2-[(1S,2S,3R,4S)-3-(diphenylphosphoryl)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]qionoline | 610300-89-5

• 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-(diphenylphosphoryl)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]qionoline
• 英文别名: 2-[(1S,2S,3R,4s)-3-(diphenylphosphoryl)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]quinoline；2-[(1S,2S,3R,4S)-3-diphenylphosphoryl-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]quinoline
• CAS: 610300-89-5
• 化学式: C₃₁H₃₂NOP
• 分子量: 465.575
• InChiKey: XVUSFIBVCROESZ-KZMPOHPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  34
• 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：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl trifluoromethanesulfonate 在 正丁基锂 、 potassium tert-butylate 、 zinc dibromide 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 为溶剂， 反应 31.75h， 生成 2-[(1S,2S,3R,4S)-3-(diphenylphosphoryl)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]qionoline
  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

• Chiral ligands and their transition metal complexes
  申请人：Scholz Ulrich

  公开号：US20070066825A1

  公开（公告）日：2007-03-22

  The present invention relates to chiral phosphorus compounds and their transition metal complexes, and also to the use of these transition metal complexes, especially in asymmetric syntheses.

  本发明涉及手性磷化合物及其过渡金属配合物，以及这些过渡金属配合物的应用，特别是在不对称合成中的应用。
• 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.