1,3-bis(3-methylbut-2-en-1-yl)-1H-indole | 28918-49-2

• 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: 1,3-bis(3-methylbut-2-en-1-yl)-1H-indole
• 英文别名: 1,3-bis(3'-methyl-2'-butenyl)-1H-indole；1,3-bis(dimethylallyl)indole；1,3-dipyrenyl indole；1,3-bis-(3-methyl-but-2-enyl)-indole；3,N-Bis-(3-methyl-but-2-enyl)-indol；1H-Indole, 1,3-bis(3-methyl-2-butenyl)-；1,3-bis(3-methylbut-2-enyl)indole
• CAS: 28918-49-2
• 化学式: C₁₈H₂₃N
• 分子量: 253.387
• InChiKey: UPOUTEVQUSEGIO-UHFFFAOYSA-N

物化性质

• 沸点：
  194-195 °C(Press: 14 Torr)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-溴-3-甲基-2-丁烯 在 potassium tert-butylate 、 氧气 作用下， 以 四氢呋喃 为溶剂， 生成 1,3-bis(3-methylbut-2-en-1-yl)-1H-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

文献信息

• Catalytic Prenylation and Reverse Prenylation of Indoles with Isoprene: Regioselectivity Manipulation through Choice of Metal Hydride
  作者：Yan‐Cheng Hu、Ding‐Wei Ji、Chao‐Yang Zhao、Hao Zheng、Qing‐An Chen

  DOI：10.1002/anie.201901025

  日期：2019.4.8

  The basic industrial feedstock isoprene was employed as a building block to install prenyl and reverse‐prenyl groups onto indoles. The regioselectivity can be manipulated by the choice of metal hydride. Reverse‐prenylated indoles were attained with high selectivity when using Rh−H. By switching to a Pd−H catalyst, selectivity toward prenylated indoles was achieved. This regiodivergent method also features

  基本的工业原料异戊二烯被用作将异戊二烯基和反向异戊二烯基安装到吲哚上的结构单元。区域选择性可以通过选择金属氢化物来控制。使用Rh-H时，可以实现高选择性的反向异戊二烯基吲哚。通过转换为Pd-H催化剂，可以实现对烯丙基化吲哚的选择性。该区域发散方法还具有高原子经济性而无化学计量副产物形成的特征。
• Synthesis of 2-(dimethylallyl)-N-hydroxytryptophans from indole
  作者：Ralf Plate、Harry C.J Ottenheijm

  DOI：10.1016/s0040-4039(00)83872-1

  日期：1986.1

  method for the synthesis of dimethylallyl tryptophan derivatives 11 and 12 is described. Reaction of the 3-(γ, γ-dimethyl-allyl) indoles 7a or 7b with the nitroso olefin 8 yields the cycloadducts 9a (93%) and 9b (87%), respectively. Subsequent treatment of 9a with trifluoroacetic acid affords the 2-(dimethylallyl) tryptophan derivatives 11a and 12a in a 9:1 ratio (97% yield). Isomerisation of 9b gave

  描述了合成二甲基烯丙基色氨酸衍生物11和12的温和且通用的方法。3-（γ，γ-二甲基-烯丙基）吲哚7a或7b与亚硝基烯烃8的反应分别产生环加合物9a（93％）和9b（87％）。随后用三氟乙酸处理9a，以9∶1的比例得到2-（二甲基烯丙基）色氨酸衍生物11a和12a（97％收率）。9b的异构化仅产生11b（88％收率）。
• 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.
• 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 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.