2-(1-(1-methyl-1H-indol-3-yl)ethyl)phenol | 1295507-24-2

• 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: 2-(1-(1-methyl-1H-indol-3-yl)ethyl)phenol
• 英文别名: 2-[1-(1-Methylindol-3-yl)ethyl]phenol；2-[1-(1-methylindol-3-yl)ethyl]phenol
• CAS: 1295507-24-2
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: RPMRGBAAUPGRBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  水杨醛 在 tris-(dibenzylideneacetone)dipalladium(0) 、 氯丁烷 、 potassium tert-butylate 、 potassium hydrogencarbonate 、 三环己基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 76.0h， 生成 2-(1-(1-methyl-1H-indol-3-yl)ethyl)phenol
  参考文献：
  名称：

  Palladium-Catalyzed Hydrofunctionalization of Vinyl Phenol Derivatives with Heteroaromatics

  摘要：

  A hydroheteroarylation reaction of vinyl phenols using an alkyl chloride as the sacrificial hydride source is reported. The method tolerates a wide range of heterocycles as the exogenous nucleophile including indoles and pyrroles. The resulting products are easily processed to biologically relevant scaffolds.

  DOI：

  10.1021/ol200913r

文献信息

• Br₂-Catalyzed regioselective dehydrative coupling of indoles with acyloins: direct synthesis of α-(3-indolyl) ketones
  作者：Deqiang Liang、Xiangguang Li、Yanni Li、Yungang Yang、Shulin Gao、Ping Cheng

  DOI：10.1039/c6ra03321k

  日期：——

  An efficient Br2-catalyzed synthesis of α-(3-indolyl) ketones via dehydrative coupling of simple indoles with acyloins is presented. This reaction proceeded with high C-3 selectivity and a wide substrate scope, and without any metal catalyst. Both the activation of alcohols by carbonyl groups and the catalysis of Br2 were essential. Density functional theory (DFT) calculations indicated that carbonyl

  提出了一种通过简单的吲哚与酰基糖苷的脱水偶联有效地利用Br 2催化合成α-（3-吲哚基）酮的方法。该反应以高的C-3选择性和宽的底物范围进行，并且没有任何金属催化剂。羰基对醇的活化和对Br 2的催化都是必不可少的。密度泛函理论（DFT）计算表明，羰基不仅增强了所形成的碳正离子的亲电性，而且还对它们起到了稳定剂的作用，并且通过Br 2和酰基醇的羟基氢之间的氢键对催化剂的活化是转型的关键过程。
• Brønsted acid-catalyzed hydroarylation of activated olefins
  作者：Ivana Fleischer、Jola Pospech

  DOI：10.1039/c4ra13647k

  日期：——

  A mild, regiospecific Brønsted acid-catalyzed hydroarylation of activated olefins, capable of the formation of quinone methide-like intermediates, has been investigated. Variously substituted 2- and 4-vinylphenols, 4-vinylaniline or 6-vinyl-naphthalen-2-ol were successfully implemented in a sequential protonation and Friedel–Crafts-type alkylation reaction of electron-rich arenes.

  研究了温和的，区域特异性的布朗斯台德酸催化的活化烯烃的加氢芳基化反应，该反应能够形成类似醌甲基化物的中间体。在富电子芳烃的顺序质子化和Friedel-Crafts型烷基化反应中，成功实现了各种取代的2-和4-乙烯基苯酚，4-乙烯基苯胺或6-乙烯基萘-2-醇。
• Palladium-Catalyzed Hydrofunctionalization of Vinyl Phenol Derivatives with Heteroaromatics
  作者：Tejas P. Pathak、Matthew S. Sigman

  DOI：10.1021/ol200913r

  日期：2011.5.20

  A hydroheteroarylation reaction of vinyl phenols using an alkyl chloride as the sacrificial hydride source is reported. The method tolerates a wide range of heterocycles as the exogenous nucleophile including indoles and pyrroles. The resulting products are easily processed to biologically relevant scaffolds.