(E)-1,2-dimethyl-3-styryl-1H-indole | 72228-49-0

• 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: (E)-1,2-dimethyl-3-styryl-1H-indole
• 英文别名: 1,2-dimethyl-3-[(E)-2-phenylethenyl]indole
• CAS: 72228-49-0
• 化学式: C₁₈H₁₇N
• 分子量: 247.34
• InChiKey: RNKYIMCQCMZDQJ-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 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

• 作为反应物：
  描述：

  (E)-1,2-dimethyl-3-styryl-1H-indole 在 tetraphenylporphyrin 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以30%的产率得到9,9a-Dimethyl-3-phenyl-9,9a-dihydro-3H-[1,2]dioxino[3,4-b]indole
  参考文献：
  名称：

  .alpha.-Lithio-3-indolylacetate synthons: generation and synthetic utilization

  摘要：

  DOI：

  10.1021/jo01291a014
• 作为产物：
  描述：

  3,3′-(2-phenylethane-1,1-diyl)bis(1,2-dimethyl-1H-indole) 在 乙醇 、 iron(III) chloride hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (E)-1,2-dimethyl-3-styryl-1H-indole
  参考文献：
  名称：

  FeCl₃·6H₂O-Catalyzed Alkenylation of Indoles with Aldehydes

  摘要：

  FeCl3 center dot 6H(2)O-catalyzed efficient C3-alkenylation of indoles was realized through the condensation of aldehydes and indole derivatives in the presence of 2 equiv of ethanol at ambient temperature, forming 3-vinylindoles in up to 93% yields. Ethanol promoted formation of the desired products. An obvious solvent effect was observed, and bisindoles were identified as the reaction intermediates.

  DOI：

  10.1021/jo301416s

文献信息

• Condensation of Indoles and Aldehydes in Subcritical Water without the Addition of Catalysts
  作者：Tsunehisa Hirashita、Masaki Ogawa、Reina Hattori、Sota Okochi、Shuki Araki

  DOI：10.1246/bcsj.20150247

  日期：2015.12.15

  A series of 3,3′-diindolylmethanes were prepared in high yields from indoles and aldehydes under subcritical water conditions without the addition of catalysts. 3-Alkenylindoles were also obtained ...

  在亚临界水条件下，在不添加催化剂的情况下，由吲哚和醛以高产率制备了一系列 3,3'-二吲哚基甲烷。还获得了 3-烯基吲哚...
• Aerobic Dehydrogenative Heck Reactions of Heterocycles with Styrenes: A Negative Effect of Metallic Co-Oxidants
  作者：Alexandre Vasseur、Dominique Harakat、Jacques Muzart、Jean Le Bras

  DOI：10.1002/adsc.201200787

  日期：2013.1.14

  The aerobic dehydrogenative Heck reaction (DHR) of heterocycles with styrenes was found to be more efficient in the absence of metallic co‐oxidants. According to a study of the isotope effect, the CH cleavage was the rate‐determining step of the catalytic cycle. Electrospray ionization mass spectrometry, subsequent MS/MS, and high‐resolution mass spectrometry were used to detect and characterize catalytic

  发现在没有金属助氧化剂的情况下，杂环与苯乙烯的好氧脱氢Heck反应（DHR）更有效。根据对同位素效应的研究，CH裂解是催化循环的速率决定步骤。电喷雾电离质谱，随后的MS / MS和高分辨率质谱用于检测和表征在金属共氧化剂存在下形成的催化中间体和物种。
• ADAM W.; TAKAYAMA K., J. ORG. CHEM., 1980, 45, NO 3, 447-452
  作者：ADAM W.、 TAKAYAMA K.

  DOI：——

  日期：——