(3S*,5R*,8aR*)-3-ethyl-5-methyl-1,2,3,5,6,7,8,8a-octahydroindolizine

• 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: (3S*,5R*,8aR*)-3-ethyl-5-methyl-1,2,3,5,6,7,8,8a-octahydroindolizine
• 英文别名: 3-ethyl-5-methylindolizidine；indolizidine 167E；(3S,5R,8aR)-3-ethyl-5-methyl-1,2,3,5,6,7,8,8a-octahydroindolizine
• 化学式: C₁₁H₂₁N
• 分子量: 167.294
• InChiKey: QTKAOBFOSUKTSE-OUAUKWLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6-allyl-4-(phenylthio)-1,2,5,6-tetrahydropyridin-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 copper(l) iodide 、 potassium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 15.0h， 生成 (3S*,5R*,8aR*)-3-ethyl-5-methyl-1,2,3,5,6,7,8,8a-octahydroindolizine
  参考文献：
  名称：

  New synthesis and reactions of indolizidine 167E and indolizidine derivatives

  摘要：

  Two new methods of synthesizing indolizidines via ring-closing metathesis (RCM) have been developed. One method utilizes an alkene-isomerization, and the other method uses N-vinylation of an amide as the key step. Indolizidine 167E and many derivatives have also been synthesized. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.026

文献信息

• Tandem cross metathesis and intramolecular aza-Michael reaction to synthesize bicyclic piperidines and indolizidine 167E
  作者：Shang-Shing P. Chou、Jhih-Liang Huang

  DOI：10.1016/j.tetlet.2012.08.031

  日期：2012.10

  We have successfully transformed the terminal alkenes of dihydropyridones to the alpha,beta-unsaturated esters by cross metathesis (CM). After detosylation the secondary amides can undergo the intramolecular aza-Michael reaction to give the bicyclic piperidine structures. The stereoselectivity of the aza-Michael reaction is determined by the size of the newly formed ring. With simple transformations we have also achieved the synthesis of indolizidine 167E. (C) 2012 Elsevier Ltd. All rights reserved.
• New synthesis and reactions of indolizidine 167E and indolizidine derivatives
  作者：Shang-Shing P. Chou、Shan-Lun Chiang、Guan-Lin Huang、Bi-Shan Chiang、Ya-Chien Yu

  DOI：10.1016/j.tet.2012.10.026

  日期：2013.1

  Two new methods of synthesizing indolizidines via ring-closing metathesis (RCM) have been developed. One method utilizes an alkene-isomerization, and the other method uses N-vinylation of an amide as the key step. Indolizidine 167E and many derivatives have also been synthesized. (C) 2012 Elsevier Ltd. All rights reserved.