(R)-2-(二苯基膦)-1-苯乙胺 | 141096-35-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (R)-2-(二苯基膦)-1-苯乙胺
• 中文别名: (R)-2-(二苯基膦)-1-苯基乙胺；(R)-2-二苯基膦基-1-苯基乙基胺；(ΑR)-Α-[(二苯基膦)甲基]苯甲胺；(R)-2 - (二苯基膦)- 1 -苯乙胺
• 英文名称: (R)-2-(diphenylphosphanyl)-1-phenylethan-1-amine
• 英文别名: (R)-2-(diphenylphosphano)-1-phenylethylamine；(R)-2-(Diphenylphosphino)-1-phenylethanamine；(1R)-2-diphenylphosphanyl-1-phenylethanamine
• CAS: 141096-35-7
• 化学式: C₂₀H₂₀NP
• mdl: MFCD17013988
• 分子量: 305.359
• InChiKey: OTNYDYNCOCRMDG-FQEVSTJZSA-N

物化性质

• 沸点：
  445.3±38.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

SDS

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Section 1: Product Identification
Chemical Name: (R)-2-(Diphenylphosphino)-1-phenylethylamine, min. 97%
CAS Registry Number: 141096-35-7
Formula: C26H24NP
EINECS Number: none
Chemical Family: organophosphine ligand
Synonym: none

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Section 2: Composition and Information on Ingredients
Ingredient CAS Number Percent ACGIH (TWA) OSHA (PEL)
Title compound 141096-35-7 100% no data no data

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Section 3: Hazards Identification
Emergency Overview: Irritating to skin, eyes and respiratory tract. May be harmful if swallowed.
Primary Routes of Exposure: Ingestion, inhalation
Eye Contact: Causes moderate irritation of the eyes.
Skin Contact: Causes slight to mild irritation of the skin.
Inhalation: Irritating to the nose, mucous membranes and respiratory tract.
Ingestion: No information available on the physiological effects of ingestion. May be harmful if swallowed.
Acute Health Affects: Irritating to skin, eyes and respiratory tract.
Chronic Health Affects: No information on long-term chronic effects.
NTP: No
IARC: No
OSHA: No

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SECTION 4: First Aid Measures
Immediately flush the eyes with copious amounts of water for at least 10-15 minutes. A victim may need
Eye Exposure:
assistance in keeping their eye lids open. Get immediate medical attention.
Wash the affected area with water. Remove contaminated clothes if necessary. Seek medical assistance if
Skin Exposure:
irritation persists.
Remove the victim to fresh air. Closely monitor the victim for signs of respiratory problems, such as difficulty
Inhalation:
in breathing, coughing, wheezing, or pain. In such cases seek immediate medical assistance.
Seek medical attention immediately. Keep the victim calm. Give the victim water (only if conscious). Induce
Ingestion:
vomiting only if directed by medical personnel.

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SECTION 5: Fire Fighting Measures
Flash Point: no data
Autoignition Temperature: no data
Explosion Limits: no data
Extinguishing Medium: carbon dioxide, dry powder or foam
If this product is involved in a fire, fire fighters should be equipped with a NIOSH approved positive pressure
Special Fire Fighting Procedures:
self-contained breathing apparatus and full protective clothing.
Hazardous Combustion and If involved in a fire this material may emit irritating fumes.
Decomposion Products:
Unusual Fire or Explosion Hazards: No unusual fire or explosion hazards.

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SECTION 6: Accidental Release Measures
Spill and Leak Procedures: Small spills can be mixed with vermiculite or sodium carbonate and swept up.

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SECTION 7: Handling and Storage
Store in a tightly sealed container under an inert atmosphere of nitrogen or argon. Keep in a cool, dry, well
Handling and Storage:
ventilated place.

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SECTION 8: Exposure Controls and Personal Protection
Eye Protection: Always wear approved safety glasses when handling a chemical substance in the laboratory.
Skin Protection: Wear protective clothing and gloves.
Ventilation: Handle the material in an efficient fume hood.
If ventilation is not available a respirator should be worn. The use of respirators requires a Respirator
Respirator:
Protection Program to be in compliance with 29 CFR 1910.134.
Ventilation: Handle the material in an efficient fume hood.
Additional Protection: No additional protection required.

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SECTION 9: Physical and Chemical Properties
Color and Form: white solid
Molecular Weight: 381.43
Melting Point: no data
Boiling Point: no data
Vapor Pressure: no data
Specific Gravity: no data
Odor: none
Solubility in Water: Insoluble

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SECTION 10: Stability and Reactivity
Stability: air sensitive
Hazardous Polymerization: no hazardous polymerization
Conditions to Avoid: prolonged exposure to air
Incompatibility: strong oxidizing agents
Decomposition Products: carbon monoxide, carbon dioxide, nitrogen oxides, phosphorous oxides and organic fumes

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SECTION 11: Toxicological Information
RTECS Data: No information available in the RTECS files
Carcinogenic Effects: No data
Mutagenic Effects: No data
Tetratogenic Effects: No data

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SECTION 12: Ecological Information
Ecological Information: No information available

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SECTION 13: Disposal Considerations
Disposal: Dispose of according to local, state and federal regulations.

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SECTION 14: Transportation
Shipping Name (CFR): Non-hazardous
Hazard Class (CFR): NA
Additional Hazard Class (CFR): NA
Packaging Group (CFR): NA
UN ID Number (CFR): NA
Shipping Name (IATA): Non-hazardous
Hazard Class (IATA): NA
Additional Hazard Class (IATA): NA
Packaging Group (IATA): NA
UN ID Number (IATA): NA

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SECTION 15: Regulatory Information
TSCA: Not listed in the TSCA inventory
SARA (Title 313): Not reportable under SARA 313.
Second Ingredient: none

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (R)-2-(二苯基膦)-1-苯乙胺 在 silver trifluoromethanesulfonate 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 [(2R)-2-[(2R)-2-ethenylpyrrolidin-1-yl]-2-phenylethyl]-diphenylphosphane
  参考文献：
  名称：

  功能化吡咯烷的不对称合成。硫化物和亚砜配体介导的高度非对映选择性环化

  摘要：

  银（I）催化的硫化物1b和亚砜4和5的环化反应分别得到相应的2-乙烯基吡咯烷2b，6a和7a，其非对映选择性高（高达99％的非对映异构体过量）水平；在所有这些情况下，已经证明观察到的不对称感应是相同的。

  DOI：

  10.1039/c39920000335
• 作为产物：
  描述：

  D-苯甘氨醇 在 对甲苯磺酰氯 作用下， 以 乙酸乙酯 为溶剂， 生成 (R)-2-(二苯基膦)-1-苯乙胺
  参考文献：
  名称：

  功能化吡咯烷的不对称合成。硫化物和亚砜配体介导的高度非对映选择性环化

  摘要：

  银（I）催化的硫化物1b和亚砜4和5的环化反应分别得到相应的2-乙烯基吡咯烷2b，6a和7a，其非对映选择性高（高达99％的非对映异构体过量）水平；在所有这些情况下，已经证明观察到的不对称感应是相同的。

  DOI：

  10.1039/c39920000335

文献信息

• Cobalt-catalyzed asymmetric hydrogenation of ketones: A remarkable additive effect on enantioselectivity
  作者：Tian Du、Biwen Wang、Chao Wang、Jianliang Xiao、Weijun Tang

  DOI：10.1016/j.cclet.2020.09.011

  日期：2021.3

  achiral electron-rich mono-phosphine ligand, catalyzes efficient asymmetric hydrogenation of a wide range of aryl ketones, affording chiral alcohols with high yields and moderate to excellent enantioselectivities (29 examples, up to 93% ee). Notably, the achiral mono-phosphine ligand shows a remarkable effect on the enantioselectivity of the reaction.

  手性钴夹钳配合物，与非手性富电子的单膦配体结合，可催化多种芳基酮的有效不对称氢化，提供高收率和中等至优异对映选择性的手性醇（29例，最高93％ee）。值得注意的是，非手性单膦配体对反应的对映选择性表现出显着的影响。
• <i>C1</i>-Symmetric PNP Ligands for Manganese-Catalyzed Enantioselective Hydrogenation of Ketones: Reaction Scope and Enantioinduction Model
  作者：Liyao Zeng、Huaxin Yang、Menglong Zhao、Jialin Wen、James H. R. Tucker、Xumu Zhang

  DOI：10.1021/acscatal.0c04206

  日期：2020.12.4

  ferrocene-based chiral PNP ligands is reported. These tridentate ligands were successfully applied in Mn-catalyzed asymmetric hydrogenation of ketones, giving high enantioselectivities (92%∼99% ee for aryl alkyl ketones) as well as high efficiencies (TON up to 2000). In addition, dialkyl ketones could also be hydrogenated smoothly. Manganese intermediates that might be involved in the catalytic cycle were analyzed

  报道了基于二茂铁的手性PNP配体家族。这些三齿配体已成功应用于锰催化的酮的不对称加氢反应中，具有很高的对映选择性（芳基烷基酮的ee为92％〜99％ee）以及高效率（TON高达2000）。另外，二烷基酮也可以平稳地氢化。分析了可能参与催化循环的锰中间体。进行了DFT计算以帮助理解手性诱导模型。Mn / PNP催化剂可通过柔性5元环中的膦部分变形来区分具有不同空间特性的两个基团。
• [EN] METHOD FOR PRODUCING AMIDINE DERIVATIVES<br/>[FR] PROCÉDÉ DE PRODUCTION DE DÉRIVÉS D'AMIDINE
  申请人：BIOCRYST PHARM INC

  公开号：WO2016029216A2

  公开（公告）日：2016-02-25

  The invention provides methods and intermediates useful in the synthesis of a compound of formula (I): or a pharmaceutically acceptable salt, solvate, ester or prodrug thereof; wherein the variables are as defined herein.

  本发明提供了用于合成式(I)化合物的方法和中间体，或其药学上可接受的盐、溶剂和前药酯；其中变量如本文所定义。
• Design, Synthesis, and Preclinical Activity in Ovarian Cancer Models of New Phosphanegold(I)-N-heterocyclic Carbene Complexes
  作者：Adam A. A. Sulaiman、Naike Casagrande、Cinzia Borghese、Giuseppe Corona、Anvarhusein A. Isab、Saeed Ahmad、Donatella Aldinucci、Muhammad Altaf

  DOI：10.1021/acs.jmedchem.2c00737

  日期：2022.11.10

  than cisplatin and auranofin in OvCa cells sensitive and resistant to cisplatin. The anticancer activity of the most active complex 6 was investigated using OvCa in vitro models, including three-dimensional (3D) multicellular tumor spheroids and in vivo tumor xenografts. Both cisplatin and auranofin were used for comparative purposes. Complex 6 induced apoptosis, mitochondrial reactive oxygen species,

  合成了一系列包含 1,3-双(2,6-二异丙基苯基)咪唑-2-亚基 (IPr) 和膦配体 (L1–L7)的七种金 (I) 配合物 ( 1 – 7 )，并评估了其抗肿瘤作用卵巢癌 (OvCa) 模型中的活性。通过红外光谱、质谱和核磁共振光谱对合成的配合物进行了表征，配合物6通过XRD晶体学进行了表征。在对顺铂敏感和耐药的 OvCa 细胞中，新复合物 ( 1 – 7 ) 的抗增殖作用被发现高于顺铂和金诺芬。使用 OvCa在体外研究了最活跃的复合物6的抗癌活性模型，包括三维 (3D) 多细胞肿瘤球体和体内肿瘤异种移植物。顺铂和金诺芬都用于比较目的。复合物6诱导细胞凋亡、线粒体活性氧和 DNA 损伤；引起 G1 期细胞周期停滞，抑制蛋白酶体活性和细胞迁移；改性肌动蛋白聚合；并显着抑制 OvCa 小鼠异种移植物。这些有希望的结果表明对这些复合物进行进一步的临床前测试以供将来应用。