(2S,3S)-(+)-2,3-双(二苯基膦基)双环[2.2.1]庚-5-烯

(2S,3S)-(+)-2,3-双(二苯基膦基)双环[2.2.1]庚-5-烯 基本信息
CAS号 71042-54-1 分子式 C31H28P2
分子量 462.50200 精确质量 　462.16700
PSA 　27.18000 LogP 　6.19530
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等价的CAS号：

71042-54-1,71042-55-2,76740-45-9,121902-85-0
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目录
基本信息 制备方法与用途 物化性质 安全信息 合成路线 MSDS 海关数据 结构与计算数据 上下游

基本信息 展开↓

CAS号：
71042-54-1
3D弹球模型：
立即前往扯扯看
分子式：
C31H28P2
分子量：
462.50200
中文名称：
(2S,3S)-(+)-2,3-双(二苯基膦基)双环[2.2.1]庚-5-烯
英文名称：
(2S,3S)-(+)-2,3-BIS(DIPHENYLPHOSPHINO)-BICYCLO[2.2.1]HEPT-5-ENE
中文别名：
(2S,3S)-(+)-2,3-双(二苯基膦基)双环[2.2.1]庚-5-烯;
(2R,3R)-(-)-2,3-双(二苯基膦)二环[2.2.1]庚基-5-烯
英文别名：
(2S,3S)-(+)-2,3-BIS(DIPHENYLPHOSPHINO)-BICYCLO[2.2.1]HEPT-5-ENE;
(2R,3R)-(-)-2,3-Bis(diphenylphosphino)bicyclo[2.2.1]hept-5-ene;
(S,S)-2,3-bis(diphenylphosphanyl)bicyclo[2.2.1]hept-5-ene;
(2S,3S)-(+)-2,3-Bis(diphenylphosphino)-bicylo[2.2.1]hept-5-ene;
(S,S)-Norphos;
(2S,3S)-(+)-Norphos;
(+)-norphos;
(2S,3S)-(+)-bis(diphenylphosphanyl)bicyclo[2.2.1]hept-5-ene
精确分子量/精确质量：
462.16700
极性分子表面积/PSA：
27.18000
油水分配系数/LogP：

LogP值指的是某物质在正辛醇/水两相体系中的分配系数的对数值，反映了物质在油水两相中的分配情况。其中、LogP值越大，说明该物质越亲油；反之，LogP值越小，则说明该物质越亲水。
InChI：
InChI=1/C31H28P2/c1-5-13-26(14-6-1)32(27-15-7-2-8-16-27)30-24-21-22-25(23-24)31(30)33(28-17-9-3-10-18-28)29-19-11-4-12-20-29/h1-22,24-25,30-31H,23H2/t24?,25?,30-,31-/m0/s1

生产制备方法及用途展开↓

制备方法

通过还原剂还原(+)-trans-(2S,3S)-二(二苯基氧化膦)二环庚-5-烯制得的。

合成制备方法

通过还原剂还原(+)-trans-(2S,3S)-二(二苯基氧化膦)二环[2.2.1]庚-5-烯制得的[1]。

用途简介

不对称催化加氢反应过渡金属与(+)- NORPHOS形成的配合物可以广泛用于不饱和官能团的催化加氢。由配合物[Rh(diene)Cl]2与(+)-NORPHOS反应得到的铑催化剂可用于催化加氢反应 (式1)。Rh与(+)-NORPHOS形成的配合物也可用于碳-氧双键 (式2) 和碳-氮双键 (式3) 的不对称加成，与其它试剂相比，应用(+)-NORPHOS可得到更高产率的立体专一产物。在苄胺存在下，Rh与(–)-NORPHOS形成的这种配合物对α-酮酸进行氢化，可得到立体专一性的α-苄氨基酸 (式4)。不对称硼氢化反应在Rh与(+)-NORPHOS形成的配合物催化下，环丙烯衍生物进行硼氢化反应，可得到很高立体专一性产物 (式5)。类Diels-Alder反应乙酸钴/(+)-NORPHOS催化剂使得降冰片二烯(norbornadiene)与单取代的炔烃加成，得到高立体专一性 (大于98% ee) 的四环烯烃 (式6)。(R,R)-(－)-N,N'-二(3,5-二叔丁基亚水杨基)-1,2-二氨基环己基氯化锰(III)不对称烯烃的芳基化在Pd(II)/(+)-NOR- PHOS的配合物催化下，降冰片烯能与碘代芳烃发生不对称加成反应 (式7)。

用途

不对称催化加氢反应  过渡金属与(+)- NORPHOS形成的配合物可以广泛用于不饱和官能团的催化加氢。由配合物[Rh(diene)Cl]2与(+)-NORPHOS反应得到的铑催化剂可用于催化加氢反应 (式1)[1]。

Rh与(+)-NORPHOS形成的配合物也可用于碳-氧双键 (式2)[2] 和碳-氮双键 (式3)[3] 的不对称加成，与其它试剂相比，应用(+)-NORPHOS可得到更高产率的立体专一产物。在苄胺存在下，Rh与(–)-NORPHOS形成的这种配合物对α-酮酸进行氢化，可得到立体专一性的α-苄氨基酸 (式4)[4]。

不对称硼氢化反应  在Rh与(+)-NORPHOS形成的配合物催化下，环丙烯衍生物进行硼氢化反应，可得到很高立体专一性产物 (式5)[5]。

类Diels-Alder反应  乙酸钴/(+)-NORPHOS催化剂使得降冰片二烯(norbornadiene)与单取代的炔烃加成，得到高立体专一性 (大于98% ee) 的四环烯烃 (式6)[6]。

(R,R)-(－)-N,N'-二(3,5-二叔丁基亚水杨基)-1,2-二氨基环己基氯化锰(III)

物化性质展开↓

外观与性状：
白色晶体
熔点：
120ºC
稳定性相关：

易被氧化，应在氮气或氩气保护下操作，操作在通风橱中进行。

其它信息：

1.       性状：未确定

2.       密度（g/mL,25/4℃）：未确定

3.       相对蒸汽密度（g/mL,空气=1）：未确定

4.       熔点（ºC）：129-130

5.       沸点（ºC,常压）：未确定

6.       沸点（ºC,5.2kPa）：未确定

7.       折射率：未确定

8.       闪点（ºC）：未确定

9.       比旋光度（º）：未确定

10.    自燃点或引燃温度（ºC）：未确定

11.    蒸气压（kPa,25ºC）：未确定

12.    饱和蒸气压（kPa,60ºC）：未确定

13.    燃烧热（KJ/mol）：未确定

14.    临界温度（ºC）：未确定

15.    临界压力（KPa）：未确定

16.    油水（辛醇/水）分配系数的对数值：未确定

17.    爆炸上限（%,V/V）：未确定

18.    爆炸下限（%,V/V）：未确定

19.    溶解性：未确定

安全信息展开↓

海关代码：
2902909090
危险类别码：
R36/37/38
安全说明：
S24/25
安全标志：
S26:万一接触眼睛，立即使用大量清水冲洗并送医诊治。
:

合成路线查看所有的合成路线

  • 71075-23-5

    rac-2,3-bis(diphenylphosphoryl)bicyclo[2.2.1]hept-5-ene

  • →

  • 71042-54-1

    (2S,3S)-(+)-2,3-双(二苯基膦基)双环[2.2.1]庚-5-烯

MSDS 展开↓

Name: (2R 3R)-(-)-2 3-Bis(Diphenylphosphino)Bicyclo[2.2.1]Hept-5-ene Material Safety Data Sheet
Synonym: (R,R)-NORPHOS
CAS: 71042-54-1
Section 1 - Chemical Product   MSDS Name:(2R 3R)-(-)-2 3-Bis(Diphenylphosphino)Bicyclo[2.2.1]Hept-5-ene Material Safety Data Sheet
Synonym:(R,R)-NORPHOS
Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
71042-54-1 (2R,3R)-(-)-2,3-Bis(Diphenylphosphino) ca. 100 unlisted
Hazard Symbols: None Listed.
Risk Phrases: None Listed.
Section 3 - HAZARDS IDENTIFICATION
  EMERGENCY OVERVIEW
Air sensitive.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.
Section 4 - FIRST AID MEASURES
  Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.
Section 5 - FIRE FIGHTING MEASURES
  General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.
Section 6 - ACCIDENTAL RELEASE MEASURES
  General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation. Place under an inert atmosphere.
Section 7 - HANDLING and STORAGE
  Handling:
Wash thoroughly after handling. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Handle under an inert atmosphere. Store protected from air.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Do not expose to air. Store under an inert atmosphere.
Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
  Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 71042-54-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.
Section 9 - PHYSICAL AND CHEMICAL PROPERTIES
 
Physical State: Crystals
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 120 - 125 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density:
Molecular Formula: C31H28P2
Molecular Weight: 462.52
Section 10 - STABILITY AND REACTIVITY
  Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions. Air sensitive.
Conditions to Avoid:
Incompatible materials, dust generation, exposure to air.
Incompatibilities with Other Materials:
Oxygen, oxidizing agents, halogens.
Hazardous Decomposition Products:
Carbon monoxide, oxides of phosphorus, carbon dioxide.
Hazardous Polymerization: Will not occur.
Section 11 - TOXICOLOGICAL INFORMATION
  RTECS#:
CAS# 71042-54-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(2R,3R)-(-)-2,3-Bis(Diphenylphosphino)Bicyclo[2.2.1]Hept-5-ene - Not listed by ACGIH, IARC, or NTP.
Section 12 - ECOLOGICAL INFORMATION
 
Section 13 - DISPOSAL CONSIDERATIONS
  Dispose of in a manner consistent with federal, state, and local regulations.
Section 14 - TRANSPORT INFORMATION
 
IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Not regulated as a hazardous material.
Section 15 - REGULATORY INFORMATION
 
European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 71042-54-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 71042-54-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 71042-54-1 is not listed on the TSCA inventory.
It is for research and development use only.

SECTION 16 - ADDITIONAL INFORMATION
N/A

海关数据查看详细

中国海关编码：2902909090

概述：
2902909090. 其他芳香烃. 增值税率:17.0%. 退税率:9.0%. 监管条件:无. 最惠国关税:2.0%. 普通关税:30.0%
申报要素：
品名, 成分含量
摘要/Summary：
2902909090 other aromatic hydrocarbons。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:2.0%。General tariff:30.0%

分子结构与计算化学数据展开↓

计算化学数据

1、   疏水参数计算参考值（XlogP）：

2、   氢键供体数量：

3、   氢键受体数量：

4、   可旋转化学键数量：

5、   拓扑分子极性表面积（TPSA）：

6、   重原子数量：

7、   表面电荷：

8、   复杂度：

9、   同位素原子数量：0

10、   确定原子立构中心数量：0

11、   不确定原子立构中心数量：0

12、   确定化学键立构中心数量：0

13、   不确定化学键立构中心数量：0

14、   共价键单元数量：1

 

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  • 71075-23-5

    rac-2,3-bis(diphenylphosphoryl)bicyclo[2.2.1]hept-5-ene

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