5-methoxy-3-(3-methylbut-2-en-1-yl)-1H-indole | 477331-72-9

• 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: 5-methoxy-3-(3-methylbut-2-en-1-yl)-1H-indole
• 英文别名: 5-methoxy-3-(3-methylbut-2-enyl)-1H-indole
• CAS: 477331-72-9
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: AFQZTHYCWYGBDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 5-methoxy-3-(3-methylbut-2-en-1-yl)-1H-indole 在 potassium tert-butylate 、 三乙基硼 作用下， 以 1,4-二氧六环 、 正己烷 为溶剂， 反应 13.0h， 以80%的产率得到3-benzyl-5-methoxy-3-(3-methylbut-2-en-1-yl)-3H-indole
  参考文献：
  名称：

  N-Indolyltriethylborate: A Useful Reagent for Synthesis of C3-Quaternary Indolenines

  摘要：

  N-Indolyltriethylborate was found to be a useful reagent for dearomatizing C3-alkylation of 3-substituted indoles with both activated and nonactivated alkyl halides to give C3-quaternary indolenines, pyrroloindolines, furoindoline, and hexahydropyridoindoline under mild reaction conditions. The utility of these reagents was demonstrated in the syntheses of a pyrroloindoline-4-cholestene hybrid and debromoflustramine B.

  DOI：

  10.1021/ol4005992
• 作为产物：
  描述：

  5-甲氧基吲哚 、 天然橡胶 在 四(三苯基膦)钯 、 三乙基硼 、 (S)-(+)-5,5'-双[二(3,5-二叔丁基-4-甲氧基苯基)膦]-4,4'-二-1,3-苯并二氧戊环 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以73%的产率得到5-methoxy-3-(3-methylbut-2-en-1-yl)-1H-indole
  参考文献：
  名称：

  异戊二烯对吲哚的催化烯丙基化和反向烯丙基化：通过选择金属氢化物的区域选择性操纵

  摘要：

  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。

  DOI：

  10.1002/anie.201901025

文献信息

• Zinc-mediated Barbier reactions of pyrrole and indoles: a new method for the alkylation of pyrrole and indoles
  作者：J.S. Yadav、B.V.S. Reddy、P.Muralikrishna Reddy、Ch. Srinivas

  DOI：10.1016/s0040-4039(02)00971-1

  日期：2002.7

  Pyrrole and indoles react smoothly with alkyl halides such as allyl bromide, prenyl bromide, crotyl bromide and propargyl bromide in the presence of zinc metal in THF to afford the corresponding 3- and 2-alkyl pyrrole and 3-alkyl indole derivatives in good yields with high regioselectivity.

  在THF中存在锌金属的情况下，吡咯和吲哚与烷基卤化物（如烯丙基溴，异戊烯基溴化物，巴豆基溴化物和炔丙基溴）平稳反应，以高收率得到相应的3-和2-烷基吡咯和3-烷基吲哚衍生物。高区域选择性。
• Palladium-Catalyzed Enantioselective C-3 Allylation of 3-Substituted-1<i>H</i>-Indoles Using Trialkylboranes
  作者：Barry M. Trost、Jean Quancard

  DOI：10.1021/ja0608139

  日期：2006.5.1

  We have developed a new enantioselective C-3 allylation of 3-substituted indoles using allyl alcohol and trialkylboranes. Asymmetric syntheses of 3,3-disubstituted indolines and indolenines in enantiomeric excesses up to 90% have been achieved using the bulky borane 9-BBN-C6H13 as the promoter of the reaction. The dependence of the selectivity on the nature of the borane suggests that the boron reagent has a role beyond promoting ionization of the allyl alcohol. A protocol for oxidation of indolenines to oxindoles has also been developed and led to a formal synthesis of (-)-phenserine.
• 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。
• <i>N</i>-Indolyltriethylborate: A Useful Reagent for Synthesis of C3-Quaternary Indolenines
  作者：Aijun Lin、Jiong Yang、Mohamed Hashim

  DOI：10.1021/ol4005992

  日期：2013.4.19

  N-Indolyltriethylborate was found to be a useful reagent for dearomatizing C3-alkylation of 3-substituted indoles with both activated and nonactivated alkyl halides to give C3-quaternary indolenines, pyrroloindolines, furoindoline, and hexahydropyridoindoline under mild reaction conditions. The utility of these reagents was demonstrated in the syntheses of a pyrroloindoline-4-cholestene hybrid and debromoflustramine B.