(+)-ent-N¹-nor-debromoflustramide B | 377725-79-6

• 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-debromoflustramide B
• 英文别名: (3aS,8bR)-4,8b-bis(3-methylbut-2-enyl)-3,3a-dihydro-1H-pyrrolo[2,3-b]indol-2-one
• CAS: 377725-79-6
• 化学式: C₂₀H₂₆N₂O
• 分子量: 310.439
• InChiKey: NQQWPHMFWDUWSI-VQTJNVASSA-N

物化性质

• 沸点：
  486.7±45.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-ent-N¹-nor-debromoflustramide B 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以90%的产率得到(3aRS,8aRS)-3a,8-bis(3-methyl-2-butenyl)-1-methyl-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indol-2-one
  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：

  1,3-bis(3-methylbut-2-en-1-yl)-1H-indole 在 samarium diiodide 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 42.0h， 生成 (+)-ent-N¹-nor-debromoflustramide B
  参考文献：
  名称：

  氮杂-氧烯丙基阳离子中间体的脱芳基吲哚环加成反应：模块化获得吡咯并二氢吲哚

  摘要：

  已开发出取代吲哚与 α-卤代异羟肟酸酯的区域选择性脱芳香氮杂-(3 + 2) 环加成反应。这种转变提供了对以大量生物活性化合物为代表的高度官能化吡咯并二氢吲哚的快速获取。天然产物毒扁豆碱已使用该方法简明地合成。

  DOI：

  10.1021/jacs.5b10184

文献信息

• A new synthesis of (−)-debromoflustramine B, (+)-ent-debromoflustramine B and (+)-debromoflustramide B
  作者：A.Sofia Cardoso、Natarajan Srinivasan、Ana M Lobo、Sundaresan Prabhakar

  DOI：10.1016/s0040-4039(01)01359-4

  日期：2001.9

  The first synthesis of (-)-debromoflustramine B is reported. Appropriate structural modifications of an optically pure Barton ester, obtained in five steps from N-acetyl-L-tryptophan methyl ester, lead to the alkaloid. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Dearomative Indole Cycloaddition Reactions of Aza-Oxyallyl Cationic Intermediates: Modular Access to Pyrroloindolines
  作者：Arjun Acharya、Devendar Anumandla、Christopher S. Jeffrey

  DOI：10.1021/jacs.5b10184

  日期：2015.12.2

  A regioselective dearomative aza-(3 + 2) cycloaddition reaction of substituted indoles with α-halohydroxamates has been developed. This transformation provides rapid access to highly functionalized pyrroloindolines that are represented in large number of bioactive compounds. The natural product, physostigmine, has been concisely synthesized utilizing this method.

  已开发出取代吲哚与 α-卤代异羟肟酸酯的区域选择性脱芳香氮杂-(3 + 2) 环加成反应。这种转变提供了对以大量生物活性化合物为代表的高度官能化吡咯并二氢吲哚的快速获取。天然产物毒扁豆碱已使用该方法简明地合成。
• 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.