2-<<9-(methoxymethyl)-1(S)-(2-propenyl)-1,2,3,4-tetrahydro-β-carbolin-2-yl>methylene>valinol tert butyl ether | 133041-37-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 2-<<9-(methoxymethyl)-1(S)-(2-propenyl)-1,2,3,4-tetrahydro-β-carbolin-2-yl>methylene>valinol tert butyl ether
• CAS: 133041-37-9
• 化学式: C₂₆H₃₉N₃O₂
• 分子量: 425.615
• InChiKey: FDULJGAVLWFVCS-RXVRPDCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  38.99
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-<<9-(methoxymethyl)-1(S)-(2-propenyl)-1,2,3,4-tetrahydro-β-carbolin-2-yl>methylene>valinol tert butyl ether 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以87%的产率得到(-)-9-(methoxymethyl)-1(S)-(2-propenyl)-1,2,3,4-tetrahydro-β-carboline
  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：

  丙烯酰碘 、 (S)-(-)-2-[N-(1-tert-butoxy-3-methylbut-2-yl)iminomethyl]-9-methoxymethyl-1,2,3,4-tetrahydro-β-carboline 在 叔丁基锂 作用下， 生成 2-<<9-(methoxymethyl)-1(S)-(2-propenyl)-1,2,3,4-tetrahydro-β-carbolin-2-yl>methylene>valinol tert butyl ether
  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