1-[(2S,3aS,8bS)-2-hydroxy-4,8b-bis(3-methylbut-2-enyl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-3-yl]ethanone | 377725-74-1

• 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: 1-[(2S,3aS,8bS)-2-hydroxy-4,8b-bis(3-methylbut-2-enyl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-3-yl]ethanone
• CAS: 377725-74-1
• 化学式: C₂₂H₃₀N₂O₂
• 分子量: 354.492
• InChiKey: DHEDGLFQKABORJ-FKBYEOEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 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：
  43.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(2S,3aS,8bS)-2-hydroxy-4,8b-bis(3-methylbut-2-enyl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-3-yl]ethanone 在 lithium aluminium tetrahydride 、 sodium methylate 、 肼 作用下， 以 甲醇 、 乙醚 、 水 、 xylene 为溶剂， 反应 12.0h， 生成 (-)-(3aS,8aR)-3a,8-bis-(3'-methyl-2'-butenyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole
  参考文献：
  名称：

  A new synthesis of (−)-debromoflustramine B, (+)-ent-debromoflustramine B and (+)-debromoflustramide B

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(01)01359-4
• 作为产物：
  描述：

  methyl 1-acetyl-2,3-dihydropyrrolo<2,3-b>indole-2-carboxylate 在 氧气 、 antimony triphenylsulphide 作用下， 以 乙醚 为溶剂， 生成 1-[(2S,3aS,8bS)-2-hydroxy-4,8b-bis(3-methylbut-2-enyl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-3-yl]ethanone
  参考文献：
  名称：

  A new synthesis of (−)-debromoflustramine B, (+)-ent-debromoflustramine B and (+)-debromoflustramide B

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(01)01359-4

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.
• 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.