(2E)-(+)-ethyl 3-[(8S, 10R)-10-(trifluoromethyl)-1,5-dioxa-9-azaspiro[5.5]undec-8-yl]prop-2-enoate | 1420666-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (2E)-(+)-ethyl 3-[(8S, 10R)-10-(trifluoromethyl)-1,5-dioxa-9-azaspiro[5.5]undec-8-yl]prop-2-enoate
• CAS: 1420666-80-3
• 化学式: C₁₄H₂₀F₃NO₄
• 分子量: 323.312
• InChiKey: SLYBQNCMIQNHNS-XKFHPXPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  56.79
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2E)-(+)-ethyl 3-[(8S, 10R)-10-(trifluoromethyl)-1,5-dioxa-9-azaspiro[5.5]undec-8-yl]prop-2-enoate 在 三氟化硼乙醚 、 2-氯-1-甲基吡啶碘化物 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 (±)-(2E)-N-methoxy-N-methyl-3-[(7R,9S)-9-(trifluoromethyl)-1,4-dithia-8-azaspiro[4.5]dec-7-yl]prop-2-enamide
  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：

  (2R)-(+)-1,1,1-trifluoro-3-(2-methyl-1,3-dioxan-2-yl)-N-[(R)-1-phenylethyl]propan-2-amine 在 palladium hydroxide, 20 wt% on carbon 、 氢气 、 magnesium sulfate 作用下， 以 甲醇 、 甲苯 为溶剂， 20.0~70.0 ℃ 、344.75 kPa 条件下， 反应 4.5h， 生成 (2E)-(+)-ethyl 3-[(8S, 10R)-10-(trifluoromethyl)-1,5-dioxa-9-azaspiro[5.5]undec-8-yl]prop-2-enoate
  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