tert-butyl (R,R)-3-oxooctahydroindolizine-1-carboxylate | 1227063-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: tert-butyl (R,R)-3-oxooctahydroindolizine-1-carboxylate
• 英文别名: tert-butyl (1R,8aR)-3-oxo-2,5,6,7,8,8a-hexahydro-1H-indolizine-1-carboxylate
• CAS: 1227063-00-4
• 化学式: C₁₃H₂₁NO₃
• 分子量: 239.315
• InChiKey: JPTKCDIRRKAAJF-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (R,R)-3-oxooctahydroindolizine-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以95%的产率得到(+/-)-tashiromine
  参考文献：
  名称：

  Asymmetric synthesis of piperidines and octahydroindolizines using a one-pot ring-closure/N-debenzylation procedure

  摘要：

  The conjugate addition of an enantiopure lithium amide to a zeta-hydroxy-alpha,beta-unsaturated ester followed by a one-pot ring-closure/N-debenzylation protocol has been used in the asymmetric syntheses of (S)coniine and (R)-delta-coniceine (isolated as the corresponding hydrochloride salts), and (R,R)-1-(hydroxymethyl)octahydroindolizine (the bicyclic fragment of stellettamides A-C). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.038
• 作为产物：
  描述：

  以 氯仿 为溶剂， 反应 16.0h， 以44 mg的产率得到tert-butyl (R,R)-3-oxooctahydroindolizine-1-carboxylate
  参考文献：
  名称：

  Asymmetric synthesis of piperidines and octahydroindolizines using a one-pot ring-closure/N-debenzylation procedure

  摘要：

  The conjugate addition of an enantiopure lithium amide to a zeta-hydroxy-alpha,beta-unsaturated ester followed by a one-pot ring-closure/N-debenzylation protocol has been used in the asymmetric syntheses of (S)coniine and (R)-delta-coniceine (isolated as the corresponding hydrochloride salts), and (R,R)-1-(hydroxymethyl)octahydroindolizine (the bicyclic fragment of stellettamides A-C). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.038

文献信息

• Asymmetric Synthesis of Piperidines and Octahydroindolizines
  作者：Stephen Davies、Deri Hughes、Paul Price、Paul Roberts、Angela Russell、Andrew Smith、James Thomson、Oliver Williams

  DOI：10.1055/s-0029-1219346

  日期：2010.3

  The conjugate addition of a homochiral lithium amide to a xi-hydroxy-alpha,beta-unsaturated ester, followed by a one-pot, ring-closure-N-debenzylation protocol has been used in the asymmetric syntheses of (S)-coniine and (R)-delta-coniceine (isolated as the corresponding hydrochloride salts) and the bicyclic core of stellettamide A.