1-methyl-3-(2-phenylprop-1-enyl)-1H-indole

• 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-methyl-3-(2-phenylprop-1-enyl)-1H-indole
• 英文别名: 1-methyl-3-[(E)-2-phenylprop-1-enyl]indole
• 化学式: C₁₈H₁₇N
• 分子量: 247.34
• InChiKey: DINCUKLFKAKJES-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-[(1-methyl-1H-indol-3-yl)methyl]-1H-1,2,3-benzotriazole 在 正丁基锂 、 titanium(III) chloride 、 铜 、 锌 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 2.0h， 生成 1-methyl-3-(2-phenylprop-1-enyl)-1H-indole
  参考文献：
  名称：

  Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation

  摘要：

  Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton alpha to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and alpha,beta-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(beta-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a-j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.

  DOI：

  10.1021/jo980616v

文献信息

• β,β-Disubstituted <i>C</i>- and <i>N</i>-Vinylindoles from One-Step Condensations of Aldehydes and Indole Derivatives
  作者：Gil Fridkin、Nicolas Boutard、William D. Lubell

  DOI：10.1021/jo900526p

  日期：2009.8.7

  Direct preparation of β,β-disubstituted C- and N-vinylindoles from condensation of aldehydes on indole derivatives is presented. Heating 1-methyl- and 1-benzylindole 3a,b with alkyl and aryl α-branched aldehydes and TFA in acetonitrile using microwave irradiation furnished 3-vinylindoles 1a−e in 18−76% yields. Under similar conditions, 3-substituted indoles 4a−c provided N-vinylindoles 2a−h in 16−98%

  提出了由醛在吲哚衍生物上的缩合直接制备β，β-二取代的C-和N-乙烯基吲哚的方法。使用微波辐射，将1-甲基和1-苄基吲哚3a，b与烷基和芳基α-支化醛以及TFA在乙腈中加热，以18-76％的收率得到3-乙烯基吲哚1a - e。在相似的条件下，3-取代的吲哚4a - c以16-98％的产率提供了N-乙烯基吲哚2a - h。