3-((S)-6-Ethyl-1,4-dioxa-spiro[4.4]non-6-yl)-propionic acid methyl ester | 152266-61-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-((S)-6-Ethyl-1,4-dioxa-spiro[4.4]non-6-yl)-propionic acid methyl ester
• CAS: 152266-61-0
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: HYUHAXHGOBWJLO-LBPRGKRZSA-N

物化性质

• 沸点：
  311.1±17.0 °C(predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-((S)-6-Ethyl-1,4-dioxa-spiro[4.4]non-6-yl)-propionic acid methyl ester 在 盐酸 、 ammonium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (S)-(+)-4a-ethyl-3,4,4a,5,6,7-hexahydro-2H-1-pyridine
  参考文献：
  名称：

  Formal synthesis of (−)-Vallesamidine A 2,2,3-trialkylindoline alkaloid

  摘要：

  (S)-(+)-2-ethyl-2[2'-carboxymethyl]cyclopentanone 6 was prepared regio- and enantioselectively (ee = 90%) by ''deracemizing alkylation'' of the chiral imine 5 with methylacrylate. Compound 6 was transformed into the bicyclic imine (R)-(+)-3. This intermediate was used by Heathcock, in the racemic form, to the total synthesis of (+/-)-Vallesamidine 1, a 2,2,3-trialkylindoline alkaloid.

  DOI：

  10.1016/s0957-4166(00)80350-x
• 作为产物：
  描述：

  在 对甲苯磺酸 、 溶剂黄146 作用下， 生成 3-((S)-6-Ethyl-1,4-dioxa-spiro[4.4]non-6-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Formal synthesis of (−)-Vallesamidine A 2,2,3-trialkylindoline alkaloid

  摘要：

  (S)-(+)-2-ethyl-2[2'-carboxymethyl]cyclopentanone 6 was prepared regio- and enantioselectively (ee = 90%) by ''deracemizing alkylation'' of the chiral imine 5 with methylacrylate. Compound 6 was transformed into the bicyclic imine (R)-(+)-3. This intermediate was used by Heathcock, in the racemic form, to the total synthesis of (+/-)-Vallesamidine 1, a 2,2,3-trialkylindoline alkaloid.

  DOI：

  10.1016/s0957-4166(00)80350-x