(Z)-4-<<1(R)-(3-Butenyl)hexyl>imino>-1-butyl Acetate N-Oxide | 117960-10-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (Z)-4-<<1(R)-(3-Butenyl)hexyl>imino>-1-butyl Acetate N-Oxide
• 英文别名: 4-acetyloxy-N-[(5R)-dec-1-en-5-yl]butan-1-imine oxide
• CAS: 117960-10-8
• 化学式: C₁₆H₂₉NO₃
• 分子量: 283.411
• InChiKey: YXNYBJHNYGXOAY-MUBYSKIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  20.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-4-<<1(R)-(3-Butenyl)hexyl>imino>-1-butyl Acetate N-Oxide 在 sodium tetrahydroborate 、 草酸氯化物 、 三乙基硼氢化锂 、 potassium carbonate 、 溶剂黄146 、 二甲基亚砜 、 甲基磺酰氯 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 45.5h， 生成 (-)-indolizidine 209B
  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：

  4-acetoxy-1-butanol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-4-<<1(R)-(3-Butenyl)hexyl>imino>-1-butyl Acetate N-Oxide
  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：——
• Stereoselective synthesis of (.+-.)-indolizidines 167B, 205A, and 207A. Enantioselective synthesis of (-)-indolizidine 209B
  作者：Andrew B. Holmes、Adrian L. Smith、Simon F. Williams、Leslie R. Hughes、Zev Lidert、Colin Swithenbank

  DOI：10.1021/jo00004a012

  日期：1991.2

  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.