2-[(1S,2S,3R,4S)-3-(diphenylphosphino)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-[(1S,2S,3R,4S)-3-(diphenylphosphino)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]quinoline
• 英文别名: diphenyl-[(1S,2R,3S,4S)-4,7,7-trimethyl-3-quinolin-2-yl-2-bicyclo[2.2.1]heptanyl]phosphane
• 化学式: C₃₁H₃₂NP
• 分子量: 449.576
• InChiKey: XPISYVMNCVBBOL-KZMPOHPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  四(3,5-二(三氟甲基)苯基)硼酸钠 、 2-[(1S,2S,3R,4S)-3-(diphenylphosphino)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]quinoline 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 以 二氯甲烷 、 水 为溶剂， 以88%的产率得到Ir(1,5-cyclooctadiene)(2-(2-quinolyl)-3-(diphenylphosphanyl)bornane) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate
  参考文献：
  名称：

  用于不对称Ir催化反应的新P，N配体。

  摘要：

  DOI：

  10.1002/anie.200351936
• 作为产物：
  描述：

  2-[(1S,2S,3R,4S)-3-(diphenylphosphoryl)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]qionoline 在 三氯硅烷 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以61%的产率得到2-[(1S,2S,3R,4S)-3-(diphenylphosphino)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]quinoline
  参考文献：
  名称：

  t-BuOK-Mediated Hydrophosphination of Functionalized Alkenes:  A Novel Synthesis of Chiral P,N- and P,P-Ligands

  摘要：

  A novel synthesis of effective chiral P,N- and P,P-ligands has been developed by using a t-BuOK-mediated hydrophosphination of chiral alkenylpyridines and alkenylphosphine oxides. Ir complexes of chiral P,N-ligrands 1 and 3 gave high enantioselectivities for the hydrogenation of (Z)-alpha(acetamido)cinnamate 25 and (E)-1,2-diphenylpropene leading to the hydrogenated products with up to 97% ee.

  DOI：

  10.1021/jo030383u

文献信息

• METHOD FOR MANUFACTURING OPTICALLY ACTIVE COMPOUND
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20170022162A1

  公开（公告）日：2017-01-26

  The present invention provides a method for manufacturing an optically active compound of formula (2), which contains bringing hydrogen into contact with a compound of formula (1) in the presence of a transition metal catalyst having an optically active ligand. In the formula, R 1 represents a hydrogen atom or an acetyl group, R 2 , R 3 , R 4 , and R 5 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxy group, a nitro group, an amino group, or an acyl group, R 6 represents an alkyl group, R 7 and R 8 each independently represents a hydrogen atom or an alkyl group, and a carbon atom marked with an asterisk (*) represents an asymmetric carbon atom.

  本发明提供了一种制备式（2）的光学活性化合物的方法，其中包括在具有光学活性配体的过渡金属催化剂存在下，将氢与式（1）的化合物接触。在该式中，R1代表氢原子或乙酰基，R2、R3、R4和R5各自独立地代表氢原子、卤素原子、烷基、烷氧基、羟基、硝基、氨基或酰基，R6代表烷基，R7和R8各自独立地代表氢原子或烷基，而用星号（*）标记的碳原子代表一个不对称碳原子。
• US9796678B2
  申请人：——

  公开号：US9796678B2

  公开（公告）日：2017-10-24
• New P,N Ligands for Asymmetric Ir-Catalyzed Reactions
  作者：Tanasri Bunlaksananusorn、Kurt Polborn、Paul Knochel

  DOI：10.1002/anie.200351936

  日期：2003.8.25
• <i>t</i>-BuOK-Mediated Hydrophosphination of Functionalized Alkenes:  A Novel Synthesis of Chiral P,N- and P,P-Ligands
  作者：Tanasri Bunlaksananusorn、Paul Knochel

  DOI：10.1021/jo030383u

  日期：2004.7.1

  A novel synthesis of effective chiral P,N- and P,P-ligands has been developed by using a t-BuOK-mediated hydrophosphination of chiral alkenylpyridines and alkenylphosphine oxides. Ir complexes of chiral P,N-ligrands 1 and 3 gave high enantioselectivities for the hydrogenation of (Z)-alpha(acetamido)cinnamate 25 and (E)-1,2-diphenylpropene leading to the hydrogenated products with up to 97% ee.