(S)-N-(2-(diphenylphosphino)phenyl)methylpyrrolidine-2-carboxyamide | 1358730-16-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-N-(2-(diphenylphosphino)phenyl)methylpyrrolidine-2-carboxyamide
• 英文别名: (2S)-N-(2-diphenylphosphanylphenyl)pyrrolidine-2-carboxamide
• CAS: 1358730-16-1
• 化学式: C₂₃H₂₃N₂OP
• 分子量: 374.422
• InChiKey: MMKVFLVUZSLIIX-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-(2-(diphenylphosphino)phenyl)methylpyrrolidine-2-carboxyamide 在 双氧水 作用下， 以 氯仿 、 水 为溶剂， 反应 3.0h， 以97%的产率得到C₂₃H₂₃N₂O₂P
  参考文献：
  名称：

  Chiral phosphine-prolineamide as an organocatalyst in direct asymmetric aldol reactions

  摘要：

  Chiral phosphine-prolineamide 1a was employed as an organocatalyst in direct asymmetric aldol reactions of various aromatic aldehydes with ketones. Cyclohexanone led to the aldol products in up to 98% ee and with good diastereoselectivity using 10 mol % of TFA and 30 mol % of prolineamide 1a in DMF at 0 degrees C. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.021
• 作为产物：
  描述：

  2-二苯基膦苯甲酸 在 盐酸 、 lithium aluminium tetrahydride 、 碳酸氢铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 66.0h， 生成 (S)-N-(2-(diphenylphosphino)phenyl)methylpyrrolidine-2-carboxyamide
  参考文献：
  名称：

  Direct Asymmetric α-Allylation of Ketones with Allylic Alcohols via Pd/Enamine Cooperative Function

  摘要：

  Direct asymmetric alpha-allylation of ketones with allylic alcohols is described. The combination of palladium with a new phosphine ligand bearing a chiral proline moiety promoted the reaction to afford the corresponding alpha-allylated ketones in moderate yield and enantioselectivity.

  DOI：

  10.3987/com-12-s(n)34
• 作为试剂：
  描述：

  对三氟甲基苯甲醛 、 环己酮 在 (S)-N-(2-(diphenylphosphino)phenyl)methylpyrrolidine-2-carboxyamide 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 2-[hydroxy(4-trifluoromethylphenyl)methyl]cyclohexan-1-one 、 (S)-2-((R)-hydroxy(4-trifluoromethylphenyl)methyl)cyclohexan-1-one 、 (2R,1'S)-2-(hydroxy-(4-(trifluoromethyl)phenyl)methyl)cyclohexan-1-one
  参考文献：
  名称：

  Chiral phosphine-prolineamide as an organocatalyst in direct asymmetric aldol reactions

  摘要：

  Chiral phosphine-prolineamide 1a was employed as an organocatalyst in direct asymmetric aldol reactions of various aromatic aldehydes with ketones. Cyclohexanone led to the aldol products in up to 98% ee and with good diastereoselectivity using 10 mol % of TFA and 30 mol % of prolineamide 1a in DMF at 0 degrees C. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.021

文献信息

• Chiral phosphine-prolineamide as an organocatalyst in direct asymmetric aldol reactions
  作者：Takashi Mino、Ayaka Omura、Yukari Uda、Kazuya Wakui、Yuri Haga、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1016/j.tetasy.2011.11.021

  日期：2011.12

  Chiral phosphine-prolineamide 1a was employed as an organocatalyst in direct asymmetric aldol reactions of various aromatic aldehydes with ketones. Cyclohexanone led to the aldol products in up to 98% ee and with good diastereoselectivity using 10 mol % of TFA and 30 mol % of prolineamide 1a in DMF at 0 degrees C. (C) 2011 Elsevier Ltd. All rights reserved.
• Direct Asymmetric α-Allylation of Ketones with Allylic Alcohols via Pd/Enamine Cooperative Function
  作者：Masakatsu Shibasaki、Naoya Kumagai、Shigeo Yasuda

  DOI：10.3987/com-12-s(n)34

  日期：——

  Direct asymmetric alpha-allylation of ketones with allylic alcohols is described. The combination of palladium with a new phosphine ligand bearing a chiral proline moiety promoted the reaction to afford the corresponding alpha-allylated ketones in moderate yield and enantioselectivity.