(3E)-(-)-4-[(8R,10S)-10-(trifluoromethyl)-1,5-dioxa-9-azaspiro[5.5]undecan-8-yl]but-3-en-2-one | 1420667-59-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3E)-(-)-4-[(8R,10S)-10-(trifluoromethyl)-1,5-dioxa-9-azaspiro[5.5]undecan-8-yl]but-3-en-2-one
• CAS: 1420667-59-9
• 化学式: C₁₃H₁₈F₃NO₃
• 分子量: 293.286
• InChiKey: VGXXAZBYWGOHFI-SEUFLZDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3E)-(-)-4-[(8R,10S)-10-(trifluoromethyl)-1,5-dioxa-9-azaspiro[5.5]undecan-8-yl]but-3-en-2-one 在 palladium hydroxide, 20 wt% on carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以68%的产率得到(-)-(3'S,5'S,8a'S)-3'-methyl-5'-(trifluoromethyl)hexahydro-1'H-spiro[1,3-dioxane-2,7'-indolizine]
  参考文献：
  名称：

  Asymmetric synthesis of trifluoromethyl-piperidine based γ-amino acids and of trifluoromethyl-indolizidines

  摘要：

  The asymmetric synthesis of trifluoromethyl-piperidine-based gamma-aminoacids and of indolizidines bearing a trifluoromethyl group is reported. These rarely described compounds are prepared in a highly enantio-enriched form employing as key step an intramolecular Mannich type process, involving an enantiopure Tfm-aminoketal and ethyl oxobutenoate as aldehyde partner. Used strategy together with obtained compounds allows the access to a wide range of Tfm-N-(poly)heterocycles, structures of obvious interest for the research of new bioactive drugs. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.11.006
• 作为产物：
  描述：

  (2E)-(-)-ethyl 3-[(8R, 10S)-10-(trifluoromethyl)-1,5-dioxa-9-azaspiro[5.5]undec-8-yl]prop-2-enoate 在 manganese(IV) oxide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 9.25h， 生成 (3E)-(-)-4-[(8R,10S)-10-(trifluoromethyl)-1,5-dioxa-9-azaspiro[5.5]undecan-8-yl]but-3-en-2-one
  参考文献：
  名称：

  Asymmetric synthesis of trifluoromethyl-piperidine based γ-amino acids and of trifluoromethyl-indolizidines

  摘要：

  The asymmetric synthesis of trifluoromethyl-piperidine-based gamma-aminoacids and of indolizidines bearing a trifluoromethyl group is reported. These rarely described compounds are prepared in a highly enantio-enriched form employing as key step an intramolecular Mannich type process, involving an enantiopure Tfm-aminoketal and ethyl oxobutenoate as aldehyde partner. Used strategy together with obtained compounds allows the access to a wide range of Tfm-N-(poly)heterocycles, structures of obvious interest for the research of new bioactive drugs. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.11.006