3-[(9S)-9-ethyl-1,4-dioxaspiro[4.4]nonan-9-yl]propan-1-amine | 152266-63-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(9S)-9-ethyl-1,4-dioxaspiro[4.4]nonan-9-yl]propan-1-amine
• CAS: 152266-63-2
• 化学式: C₁₂H₂₃NO₂
• 分子量: 213.32
• InChiKey: VJJSNFZNJFAOFT-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(9S)-9-ethyl-1,4-dioxaspiro[4.4]nonan-9-yl]propan-1-amine 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以95%的产率得到(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：

  2-乙基环戊酮 在 ammonium hydroxide 、 lithium aluminium tetrahydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 3-[(9S)-9-ethyl-1,4-dioxaspiro[4.4]nonan-9-yl]propan-1-amine
  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

文献信息

• Formal synthesis of (−)-Vallesamidine A 2,2,3-trialkylindoline alkaloid
  作者：Paulo R.R. Costa、Rosane N. Castro、Florence M.C. Farias、Octavio A.C. Antunes、Lothar Bergter

  DOI：10.1016/s0957-4166(00)80350-x

  日期：1993.7

  (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.