(3RS,5SR)-2-(2'-pyridinyl)-3-hydroxy-3,5-bis-trifluoromethyl-pyrroline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (3RS,5SR)-2-(2'-pyridinyl)-3-hydroxy-3,5-bis-trifluoromethyl-pyrroline
• 英文别名: (2S,4R)-5-pyridin-2-yl-2,4-bis(trifluoromethyl)-2,3-dihydropyrrol-4-ol
• 化学式: C₁₁H₈F₆N₂O
• 分子量: 298.188
• InChiKey: WZMLNWDYPDTNBF-IONNQARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3RS,5SR)-2-(2'-pyridinyl)-3-hydroxy-3,5-bis-trifluoromethyl-pyrroline 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以94%的产率得到2-(2'-pyridinyl)-(3RS,5RS)-ditrifluoromethyl-4,5-dihydro-3H-pyrrol-3-ol
  参考文献：
  名称：

  Simple and highly diastereoselective synthesis of trifluoromethyl-containing myosmines via reaction between 2-(aminomethyl)pyridine and 1,1,1,5,5,5-hexafluoro-2,4-pentanedione

  摘要：

  The reaction between 1,1,1,5,5,5-hexafluoro-2,4-pentanedione and 2-(aminomethyl)pyridine, or its salts with carboxylic acids, was found to produce a mixture of diastereomeric 2-(2'-pyridyl)-3-hydroxy-3,5-bis-trifluoromethyl-1-pyrrolines with high (up to 85% de) of kinetic (3R*,5S*)-diastereoselectivity. The thermodynamic (3R*,5R*) diastercomer was prepared as a major product (90% de) by epimerization of the kinetic (3R*,5S*) diastereomer with triethylamine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00244-2
• 作为产物：
  描述：

  2-氨甲基吡啶 、 六氟乙酰丙酮 在 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 1.08h， 以65.3%的产率得到(3RS,5SR)-2-(2'-pyridinyl)-3-hydroxy-3,5-bis-trifluoromethyl-pyrroline
  参考文献：
  名称：

  Simple and highly diastereoselective synthesis of trifluoromethyl-containing myosmines via reaction between 2-(aminomethyl)pyridine and 1,1,1,5,5,5-hexafluoro-2,4-pentanedione

  摘要：

  The reaction between 1,1,1,5,5,5-hexafluoro-2,4-pentanedione and 2-(aminomethyl)pyridine, or its salts with carboxylic acids, was found to produce a mixture of diastereomeric 2-(2'-pyridyl)-3-hydroxy-3,5-bis-trifluoromethyl-1-pyrrolines with high (up to 85% de) of kinetic (3R*,5S*)-diastereoselectivity. The thermodynamic (3R*,5R*) diastercomer was prepared as a major product (90% de) by epimerization of the kinetic (3R*,5S*) diastereomer with triethylamine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00244-2

文献信息

• Simple and highly diastereoselective synthesis of trifluoromethyl-containing myosmines via reaction between 2-(aminomethyl)pyridine and 1,1,1,5,5,5-hexafluoro-2,4-pentanedione
  作者：Hironari Ohkura、Dmitrii O. Berbasov、Vadim A. Soloshonok

  DOI：10.1016/s0040-4039(03)00244-2

  日期：2003.3

  The reaction between 1,1,1,5,5,5-hexafluoro-2,4-pentanedione and 2-(aminomethyl)pyridine, or its salts with carboxylic acids, was found to produce a mixture of diastereomeric 2-(2'-pyridyl)-3-hydroxy-3,5-bis-trifluoromethyl-1-pyrrolines with high (up to 85% de) of kinetic (3R*,5S*)-diastereoselectivity. The thermodynamic (3R*,5R*) diastercomer was prepared as a major product (90% de) by epimerization of the kinetic (3R*,5S*) diastereomer with triethylamine. (C) 2003 Elsevier Science Ltd. All rights reserved.