(-)-N-(methoxymethyl)alloyohimban | 133160-33-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (-)-N-(methoxymethyl)alloyohimban
• 英文别名: (1S,15S,20S)-3-(methoxymethyl)-11,12,14,15,16,17,18,19,20,21-decahydro-1H-yohimban
• CAS: 133160-33-5
• 化学式: C₂₁H₂₈N₂O
• 分子量: 324.466
• InChiKey: KNMLSIHGRWGPCJ-YRNRMSPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.4
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (-)-N-(methoxymethyl)alloyohimban 在 盐酸 、 N,N-二甲基甲酰胺 作用下， 反应 72.0h， 以53%的产率得到(+/-)-alloyahimbane
  参考文献：
  名称：

  Asymmetric synthesis of yohimban alkaloids. Total synthesis of (-)-pseudo- and (-)-alloyohimban

  摘要：

  A route to (-)-pseudo and (-)-allo isomers of yohimban is described. This asymmetric synthetic approach to indole alkaloids is based on the stereocontrolled alkylation of alpha-amino carbanions mediated by chiral form-amidines. The stereochemically pure enantiomer of the alkylated beta-carboline 7 is utilized to bias the subsequent intramolecular Diels-Alder cycloaddition of the N-dienamide 8 or the homologous N-acrylamide 12 derived from the alkylated carboline 11. In this fashion, suitable choice of diene and dienophile partners led to the pseudo-and alloyohimban isomers 1b and 1c, respectively.

  DOI：

  10.1021/jo00009a007
• 作为产物：
  描述：

  (S)-(-)-2-[N-(1-tert-butoxy-3-methylbut-2-yl)iminomethyl]-9-methoxymethyl-1,2,3,4-tetrahydro-β-carboline 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 叔丁基锂 、 一水合肼 、 溶剂黄146 、 三乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， -100.0~50.0 ℃ 、344.73 kPa 条件下， 反应 41.0h， 生成 (-)-N-(methoxymethyl)alloyohimban
  参考文献：
  名称：

  Asymmetric synthesis of yohimban alkaloids. Total synthesis of (-)-pseudo- and (-)-alloyohimban

  摘要：

  A route to (-)-pseudo and (-)-allo isomers of yohimban is described. This asymmetric synthetic approach to indole alkaloids is based on the stereocontrolled alkylation of alpha-amino carbanions mediated by chiral form-amidines. The stereochemically pure enantiomer of the alkylated beta-carboline 7 is utilized to bias the subsequent intramolecular Diels-Alder cycloaddition of the N-dienamide 8 or the homologous N-acrylamide 12 derived from the alkylated carboline 11. In this fashion, suitable choice of diene and dienophile partners led to the pseudo-and alloyohimban isomers 1b and 1c, respectively.

  DOI：

  10.1021/jo00009a007

文献信息

• MEYERS, A. I.;HIGHSMITH, THOMAS K.;BUONORA, PAUL T., J. ORG. CHEM., 56,(1991) N, C. 2960-2964
  作者：MEYERS, A. I.、HIGHSMITH, THOMAS K.、BUONORA, PAUL T.

  DOI：——

  日期：——
• Asymmetric synthesis of yohimban alkaloids. Total synthesis of (-)-pseudo- and (-)-alloyohimban
  作者：A. I. Meyers、Thomas K. Highsmith、Paul T. Buonora

  DOI：10.1021/jo00009a007

  日期：1991.4

  A route to (-)-pseudo and (-)-allo isomers of yohimban is described. This asymmetric synthetic approach to indole alkaloids is based on the stereocontrolled alkylation of alpha-amino carbanions mediated by chiral form-amidines. The stereochemically pure enantiomer of the alkylated beta-carboline 7 is utilized to bias the subsequent intramolecular Diels-Alder cycloaddition of the N-dienamide 8 or the homologous N-acrylamide 12 derived from the alkylated carboline 11. In this fashion, suitable choice of diene and dienophile partners led to the pseudo-and alloyohimban isomers 1b and 1c, respectively.