(5R^*,8R,S,8aS^*)-8-Phenylselenocarbonyl-5-propyloctahydroindolizine | 117959-89-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (5R^*,8R,S,8aS^*)-8-Phenylselenocarbonyl-5-propyloctahydroindolizine
• 英文别名: Se-phenyl (5S,8aR)-5-propyl-1,2,3,5,6,7,8,8a-octahydroindolizine-8-carboselenoate
• CAS: 117959-89-4；130979-79-2
• 化学式: C₁₈H₂₅NOSe
• 分子量: 350.363
• InChiKey: LOQOAPLEDQYEDG-DRXWIORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (5R^*,8R,S,8aS^*)-8-Phenylselenocarbonyl-5-propyloctahydroindolizine 在 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 0.17h， 以62%的产率得到(5R,8aR)-5-propylindolizidine hydrochloride
  参考文献：
  名称：

  Stereoselective synthesis of (.+-.)-indolizidines 167B, 205A, and 207A. Enantioselective synthesis of (-)-indolizidine 209B

  摘要：

  The first syntheses of the dendrobatid indolizidine alkaloids 167B (3), 205A (4), and 207A (5) are described using as a key step the highly stereoselective intramolecular nitrone cycloaddition of the (Z)-N-alkenylnitrone 10 to prepare the isoxazolidine 11. Mesylate-promoted cyclization of the alcohol 12, followed by reductive cleavage of the resulting mesylate salt, afforded the key axial hydroxymethyl compound 13, which was epimerized via the aldehyde to the equatorial alcohol, and was subsequently reduced to the required 8-methyl-substituted indolizidine. The feasibility of extending this strategy to the enantioselective synthesis of such alkaloids was demonstrated in the first synthesis of (-)-indolizidine 209B (6), whose nitrone precursor 10d was obtained from the (S)-glutamate-derived amine 40.

  DOI：

  10.1021/jo00004a012
• 作为产物：
  描述：

  Oct-7-en-4-one N,N-Dimethylhydrazone 在 吡啶 、 盐酸 、 氢氧化钾 、 jones reagent 、 草酰氯 、 盐酸羟胺 、 sodium cyanoborohydride 、 溶剂黄146 、 甲基磺酰氯 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 50.17h， 生成 (5R^*,8R,S,8aS^*)-8-Phenylselenocarbonyl-5-propyloctahydroindolizine
  参考文献：
  名称：

  Stereoselective synthesis of (.+-.)-indolizidines 167B, 205A, and 207A. Enantioselective synthesis of (-)-indolizidine 209B

  摘要：

  The first syntheses of the dendrobatid indolizidine alkaloids 167B (3), 205A (4), and 207A (5) are described using as a key step the highly stereoselective intramolecular nitrone cycloaddition of the (Z)-N-alkenylnitrone 10 to prepare the isoxazolidine 11. Mesylate-promoted cyclization of the alcohol 12, followed by reductive cleavage of the resulting mesylate salt, afforded the key axial hydroxymethyl compound 13, which was epimerized via the aldehyde to the equatorial alcohol, and was subsequently reduced to the required 8-methyl-substituted indolizidine. The feasibility of extending this strategy to the enantioselective synthesis of such alkaloids was demonstrated in the first synthesis of (-)-indolizidine 209B (6), whose nitrone precursor 10d was obtained from the (S)-glutamate-derived amine 40.

  DOI：

  10.1021/jo00004a012

文献信息

• HOLMES, ANDREW B.;SMITH, ADRIAN L.;WILLIAMS, SIMON F.;HUGHES, LESLIE R.;L+, J. ORG. CHEM., 56,(1991) N, C. 1395-1405
  作者：HOLMES, ANDREW B.、SMITH, ADRIAN L.、WILLIAMS, SIMON F.、HUGHES, LESLIE R.、L+

  DOI：——

  日期：——