(S)-(1-(2-bromophenyl)pyrrolidin-2-yl)methanol | 896462-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-(1-(2-bromophenyl)pyrrolidin-2-yl)methanol
• CAS: 896462-37-6
• 化学式: C₁₁H₁₄BrNO
• 分子量: 256.142
• InChiKey: JFTJVZKXYRWYNT-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-(1-(2-bromophenyl)pyrrolidin-2-yl)methanol 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 tert-butyl bis[2-(S)-(2-methoxymethylpyrrolidinyl)phenyl] phosphine
  参考文献：
  名称：

  Preparation of N-phenyl-(S)-prolinol-derived P,N-ligands and their application in Pd-catalyzed asymmetric allylic alkylation

  摘要：

  Several NPN-type ligands bearing two chiral pyrrolidinyl groups derived from N-phenyl-(S)-prolinol were prepared by two synthetic methods. Their palladium-complex-catalyzed asymmetric allylic alkylation of malonates with 1,3-diphenyl 2-propenyl acetate delivered the products with good to high enantioselectivities (84-97% ee), including an optically active fluorine-containing compound. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.010
• 作为产物：
  描述：

  (S)-1-phenylpyrrolidine-2-carboxylic acid 在 lithium aluminium tetrahydride 、 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (S)-(1-(2-bromophenyl)pyrrolidin-2-yl)methanol
  参考文献：
  名称：

  Preparation of N-phenyl-(S)-prolinol-derived P,N-ligands and their application in Pd-catalyzed asymmetric allylic alkylation

  摘要：

  Several NPN-type ligands bearing two chiral pyrrolidinyl groups derived from N-phenyl-(S)-prolinol were prepared by two synthetic methods. Their palladium-complex-catalyzed asymmetric allylic alkylation of malonates with 1,3-diphenyl 2-propenyl acetate delivered the products with good to high enantioselectivities (84-97% ee), including an optically active fluorine-containing compound. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.010

文献信息

• Chiral P,O-ligands derived from N,O-phenylene prolinols for palladium-catalyzed asymmetric allylic alkylation
  作者：Biao Jiang、Zuo-Gang Huang

  DOI：10.1016/j.tetlet.2007.01.057

  日期：2007.3

  CuI-catalyzed N,O-arylation of (S)-prolinols and 1-bromo-2-iodobenzene afforded cyclic N,O-(1,2-phenylene)prolinols, and subsequent ortho-lithiation and phosphination provided a new type of chiral P,O-ligands. Their palladium-complex-catalyzed asymmetric allylic alkylation of dimethyl malonate with 1,3-diphenyl 2-propenyl acetate gave high yields and good enantioselectivities. (c) 2007 Elsevier Ltd. All rights reserved.
• Preparation of N-phenyl-(S)-prolinol-derived P,N-ligands and their application in Pd-catalyzed asymmetric allylic alkylation
  作者：Biao Jiang、Zuo-Gang Huang、Ke-Jun Cheng

  DOI：10.1016/j.tetasy.2006.03.010

  日期：2006.3

  Several NPN-type ligands bearing two chiral pyrrolidinyl groups derived from N-phenyl-(S)-prolinol were prepared by two synthetic methods. Their palladium-complex-catalyzed asymmetric allylic alkylation of malonates with 1,3-diphenyl 2-propenyl acetate delivered the products with good to high enantioselectivities (84-97% ee), including an optically active fluorine-containing compound. (c) 2006 Elsevier Ltd. All rights reserved.