(1,2,3,5,6,8a-hexahydroindolizin-8-yl)methanol | 131252-00-1

• 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: (1,2,3,5,6,8a-hexahydroindolizin-8-yl)methanol
• 英文别名: 1,2,3,5,6,8a-hexahydroindolizine-8-methanol；1,2,3,5,6,8a-Hexahydroindolizin-8-ylmethanol
• CAS: 131252-00-1
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: SOQBKGOROSTXTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1,2,3,5,6,8a-hexahydroindolizin-8-yl)methanol 在 Swern-oxid 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 3.92h， 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：

  [1,2,3,5,6,7,8,9-octahydro-8-(phenylsulfinyl)indolizin-8-yl]methanol 在 calcium carbonate 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以47%的产率得到(1,2,3,5,6,8a-hexahydroindolizin-8-yl)methanol
  参考文献：
  名称：

  通过基于α-亚磺酰基碳负离子的环化反应，轻松合成取代的吲哚并立生物碱：制备（±）-吲哚并立核苷167B和209D，它们的差向异构体和（±）-他四胺

  摘要：

  从简单的γ-或α-内酰胺开始，已经成功地合成了（±）-吲哚唑烷167B和209D，它们的差向异构体和（±）-tashiromine。该策略涉及将α-亚磺酰基碳负环到内酰胺环的羰基上的环化作为关键步骤，从而导致含有苯基亚磺酰基的吲哚并咪唑用作制备标题化合物的前体。

  DOI：

  10.1016/j.tet.2008.01.008

文献信息

• Rearrangement of isoxazoline-5-spiro derivatives. Part 10. Regioselective nitrone cycloadditions to methoxycarbonylmethylenecyclopropane: Synthesis of precursors of (±)-Lupinine, (±)-Epilupinine and (±)-Elaeokanine A
  作者：Franca M. Cordero、Beatrice Anichini、Andrea Goti、Alberto Brandi

  DOI：10.1016/s0040-4020(01)80188-5

  日期：1993.1

  The cycloaddition of cyclic nitrones to methoxycarbonylmethylenecyclopropane (1) gives adducts having the methoxycarbonyl group on C4 of the isoxazolidine ring with high regioselectivity. The thermal rearrangement of the adducts gives quinolizidinone 6 and indolizidinones 8 bearing the methoxycarbonyl group selectively at C-1 and at C-8, respectively. The two compounds are intermediates for new formal syntheses of the alkaloids (+/-)-Lupinine and (+/-)-Epilupinine, and (+/-)-Elaeokanine A, respectively.
• 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.
• Concise syntheses of substituted indolizidine alkaloids via cyclization based on α-sulfinyl carbanions: preparation of (±)-indolizidines 167B and 209D, their epimers, and (±)-tashiromine
  作者：Manat Pohmakotr、Saisuree Prateeptongkum、Soontorn Chooprayoon、Patoomratana Tuchinda、Vichai Reutrakul

  DOI：10.1016/j.tet.2008.01.008

  日期：2008.3

  (±)-Indolizidines 167B and 209D, their epimers and (±)-tashiromine have been successfully synthesized, starting from simple γ- or α-lactams. The strategy involves the cyclization of α-sulfinyl carbanion onto the carbonyl group of the lactam ring as the key step, leading to the indolizidines containing the phenylsulfinyl group, which are used as precursors for the preparation of the title compounds

  从简单的γ-或α-内酰胺开始，已经成功地合成了（±）-吲哚唑烷167B和209D，它们的差向异构体和（±）-tashiromine。该策略涉及将α-亚磺酰基碳负环到内酰胺环的羰基上的环化作为关键步骤，从而导致含有苯基亚磺酰基的吲哚并咪唑用作制备标题化合物的前体。