methyl 1,2,3,5,6,8a-hexahydro-3-oxoindolizine-8-carboxylate | 131251-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl 1,2,3,5,6,8a-hexahydro-3-oxoindolizine-8-carboxylate
• 英文别名: methyl 3-oxo-2,5,6,8a-tetrahydro-1H-indolizine-8-carboxylate
• CAS: 131251-99-5
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: BBWYIRNGLBPCPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  methyl 1,2,3,5,6,8a-hexahydro-3-oxoindolizine-8-carboxylate 在 Swern-oxid 、 sodium acetate 、 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 4.42h， 生成 (+/-)-elaeokanine A
  参考文献：
  名称：

  A practical preparation of the indolizidine nucleus: synthesis of (.+-.)-elaeokanine A

  摘要：

  Reduction of 3 followed by acid-catalyzed cyclization provides alpha,beta-unsaturated ester 5. As 3 can be prepared in two steps from succinimide, acrolein, and trimethyl phosphonoacetate, this is a practical method for the assembly of the indolizidine nucleus. The structure of 5 was secured by conversion to elaeokanine A, 7.

  DOI：

  10.1021/jo00003a064
• 作为产物：
  描述：

  methyl 5-(2-methoxy-5-oxo-1-pyrrolidino)-2-pentenoate 在 四氯化锡 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 methyl 1,2,3,5,6,8a-hexahydro-3-oxoindolizine-8-carboxylate
  参考文献：
  名称：

  A practical preparation of the indolizidine nucleus: synthesis of (.+-.)-elaeokanine A

  摘要：

  Reduction of 3 followed by acid-catalyzed cyclization provides alpha,beta-unsaturated ester 5. As 3 can be prepared in two steps from succinimide, acrolein, and trimethyl phosphonoacetate, this is a practical method for the assembly of the indolizidine nucleus. The structure of 5 was secured by conversion to elaeokanine A, 7.

  DOI：

  10.1021/jo00003a064

文献信息

• TABER, DOUGLASS F.;HOERRNER, R. SCOTT;HAGEN, MICHAEL D., J. ORG. CHEM., 56,(1991) N, C. 1287-1289
  作者：TABER, DOUGLASS F.、HOERRNER, R. SCOTT、HAGEN, MICHAEL D.

  DOI：——

  日期：——
• A practical preparation of the indolizidine nucleus: synthesis of (.+-.)-elaeokanine A
  作者：Douglass F. Taber、R. Scott Hoerrner、Michael D. Hagen

  DOI：10.1021/jo00003a064

  日期：1991.2

  Reduction of 3 followed by acid-catalyzed cyclization provides alpha,beta-unsaturated ester 5. As 3 can be prepared in two steps from succinimide, acrolein, and trimethyl phosphonoacetate, this is a practical method for the assembly of the indolizidine nucleus. The structure of 5 was secured by conversion to elaeokanine A, 7.