(+)-ent-N¹-nor-debromoflustramine B | 955031-11-5

• 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: (+)-ent-N¹-nor-debromoflustramine B
• 英文别名: (+)-(3aR,8aS)-3a,8-bis-(3'-methyl-2'-butenyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole；(3aS,8bR)-4,8b-bis(3-methylbut-2-enyl)-1,2,3,3a-tetrahydropyrrolo[2,3-b]indole
• CAS: 955031-11-5
• 化学式: C₂₀H₂₈N₂
• 分子量: 296.456
• InChiKey: TWRZIFGLJFJQJK-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  碘甲烷 、 (+)-ent-N¹-nor-debromoflustramine B 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以23%的产率得到(±)-debromoflustramine B
  参考文献：
  名称：

  A synthetic strategy using Witkop's pyrroloindole for (−)-debromoflustramine B, (+)-ent-debromoflustramine B and (+)-ent-debromoflustramide B

  摘要：

  While prenylation of (-)-Witkop's pyrroloindole (2), secured from L-tryptophan under standard N-alkylation conditions, led to a ca. 1: 1 diastereoisomeric mixture of two C-3a-alkylated indolenines 3 and 4, use of phase-transfer conditions altered this to ca. 1: 2. Reduction followed by N-prenylation of the resulting secondary amines gave C, N-dialkylated products. The derived separable diastereoisomeric (-)-and (+)-Barton esters 19a and 19b were then converted into (-)-debromoflustramine B and (+)-ent-debromoflustramine B, respectively. A novel reaction involving oxygen and the carbanion derived from Barton ester 19b led to (+)-ent-debromoflustramide B. Treatment of N-8-prenylated Witkop's pyrroloindole 5 with Lewis acid (BF3 center dot Et2O) uncovered a new clean intramolecular cyclisation involving the prenyl unit. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.091
• 作为产物：
  描述：

  (2-sulfanylidenepyridin-1-yl) (2S,3aR,8bR)-3-acetyl-4,8b-bis(3-methylbut-2-enyl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-2-carboxylate 在 lithium aluminium tetrahydride 、 氧气 、 sodium methylate 、 antimony triphenylsulphide 、 一水合肼 作用下， 以 甲醇 、 乙醚 、 xylene 为溶剂， 反应 14.5h， 生成 (+)-ent-N¹-nor-debromoflustramine B
  参考文献：
  名称：

  A synthetic strategy using Witkop's pyrroloindole for (−)-debromoflustramine B, (+)-ent-debromoflustramine B and (+)-ent-debromoflustramide B

  摘要：

  While prenylation of (-)-Witkop's pyrroloindole (2), secured from L-tryptophan under standard N-alkylation conditions, led to a ca. 1: 1 diastereoisomeric mixture of two C-3a-alkylated indolenines 3 and 4, use of phase-transfer conditions altered this to ca. 1: 2. Reduction followed by N-prenylation of the resulting secondary amines gave C, N-dialkylated products. The derived separable diastereoisomeric (-)-and (+)-Barton esters 19a and 19b were then converted into (-)-debromoflustramine B and (+)-ent-debromoflustramine B, respectively. A novel reaction involving oxygen and the carbanion derived from Barton ester 19b led to (+)-ent-debromoflustramide B. Treatment of N-8-prenylated Witkop's pyrroloindole 5 with Lewis acid (BF3 center dot Et2O) uncovered a new clean intramolecular cyclisation involving the prenyl unit. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.091

文献信息

• Synthesis of Isotope Labeled Me(3a)-13C-Physostigmine and Debromoflustramine B
  作者：Martha S. Morales-Ríos、Pedro Joseph-Nathan、Norma F. Santos-Sánchez、Yolanda Mora-Pérez

  DOI：10.3987/com-04-10041

  日期：——
• A synthetic strategy using Witkop's pyrroloindole for (−)-debromoflustramine B, (+)-ent-debromoflustramine B and (+)-ent-debromoflustramide B
  作者：A. Sofia P. Cardoso、M. Manuel B. Marques、Natarajan Srinivasan、Sundaresan Prabhakar、Ana M. Lobo

  DOI：10.1016/j.tet.2007.07.091

  日期：2007.10

  While prenylation of (-)-Witkop's pyrroloindole (2), secured from L-tryptophan under standard N-alkylation conditions, led to a ca. 1: 1 diastereoisomeric mixture of two C-3a-alkylated indolenines 3 and 4, use of phase-transfer conditions altered this to ca. 1: 2. Reduction followed by N-prenylation of the resulting secondary amines gave C, N-dialkylated products. The derived separable diastereoisomeric (-)-and (+)-Barton esters 19a and 19b were then converted into (-)-debromoflustramine B and (+)-ent-debromoflustramine B, respectively. A novel reaction involving oxygen and the carbanion derived from Barton ester 19b led to (+)-ent-debromoflustramide B. Treatment of N-8-prenylated Witkop's pyrroloindole 5 with Lewis acid (BF3 center dot Et2O) uncovered a new clean intramolecular cyclisation involving the prenyl unit. (C) 2007 Elsevier Ltd. All rights reserved.