2-methyl-3-(1-phenylprop-2-en-1-yl)-1H-indole | 1164108-93-3

• 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-methyl-3-(1-phenylprop-2-en-1-yl)-1H-indole
• 英文别名: 2-methyl-3-(1-phenylallyl)-1H-indole；2-methyl-3-(1-phenylprop-2-enyl)-1H-indole
• CAS: 1164108-93-3
• 化学式: C₁₈H₁₇N
• 分子量: 247.34
• InChiKey: BKKSHIWUYMXUFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(1-phenylprop-2-en-1-yl)-1H-indole 在 [Ru(η5-pentamethylcyclopentadienyl)(H₂CCHCH₂)(2-(diphenylphosphino)benzenesulfonate)]PF₆ 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 1-allyl-2-methyl-2-(1-phenylallyl)indolin-3-one
  参考文献：
  名称：

  从烯丙醇和吲哚获得3-辛辛醇

  摘要：

  使用含膦-磺酸盐螯合物的钌（IV）预催化剂对2-取代的吲哚进行位点选择性和区域选择性烯丙基化。根据反应条件有选择地获得单，二和三烯丙基吲哚，其中水是唯一的副产物。由于空气氧化了相应的烯丙基化吲哚，因此成功地完成了3-氧吲哚衍生物的制备。事实证明，二烯丙基化的拟吲哚酚是一种很好的合成子，可以通过闭环易位反应进行环化反应，从而提供相应的三环加合物。测量了3-氧吲哚的光物理性质，某些化合物在水中显示出强荧光。

  DOI：

  10.1002/chem.201800348
• 作为产物：
  描述：

  苯甲醛 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 硫酸 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 2-methyl-3-(1-phenylprop-2-en-1-yl)-1H-indole
  参考文献：
  名称：

  Iridium-Catalyzed C-3 Allylation of Indoles with Allylic Alcohols Promoted by a Brønsted Acid

  摘要：

  A highly regioselective method has been developed for the allylation of indoles with an iridium catalyst. This regioselective procedure uses allylic alcohols directly as allylating agents in the presence of a catalytic amount of sulfuric acid. A wide range of indoles reacted smoothly with asymmetrical allylic alcohols to give the corresponding branched products in branched-to-linear ratios of up to 99: 1 and yields as high as 92%. A series of inorganic and organic acids were tested in this approach, and it was shown that acids with pK(a) values in acetonitrile of less than 15 are required in this iridium-catalyzed system.

  DOI：

  10.1055/s-0033-1341156

文献信息

• Iridium-Catalyzed C-3 Allylation of Indoles with Allylic Alcohols Promoted by a Brønsted Acid
  作者：Chun Cai、Shu-jie Chen、Guo-ping Lu

  DOI：10.1055/s-0033-1341156

  日期：——

  A highly regioselective method has been developed for the allylation of indoles with an iridium catalyst. This regioselective procedure uses allylic alcohols directly as allylating agents in the presence of a catalytic amount of sulfuric acid. A wide range of indoles reacted smoothly with asymmetrical allylic alcohols to give the corresponding branched products in branched-to-linear ratios of up to 99: 1 and yields as high as 92%. A series of inorganic and organic acids were tested in this approach, and it was shown that acids with pK(a) values in acetonitrile of less than 15 are required in this iridium-catalyzed system.
• Access to 3-Oxindoles from Allylic Alcohols and Indoles
  作者：Hortense Lauwick、Yang Sun、Huriye Akdas-Kilig、Sylvie Dérien、Mathieu Achard

  DOI：10.1002/chem.201800348

  日期：2018.6.4

  The preparation of 3‐oxindole derivatives was then successfully performed owing to air oxidation of the corresponding allylated indoles. Diallylated pseudoindoxyls were proven to be good synthons to perform cyclization through a ring‐closing metathesis reaction to afford the corresponding tricyclic adducts. The photophysical properties of the 3‐oxindoles were measured, and some of the compounds showed

  使用含膦-磺酸盐螯合物的钌（IV）预催化剂对2-取代的吲哚进行位点选择性和区域选择性烯丙基化。根据反应条件有选择地获得单，二和三烯丙基吲哚，其中水是唯一的副产物。由于空气氧化了相应的烯丙基化吲哚，因此成功地完成了3-氧吲哚衍生物的制备。事实证明，二烯丙基化的拟吲哚酚是一种很好的合成子，可以通过闭环易位反应进行环化反应，从而提供相应的三环加合物。测量了3-氧吲哚的光物理性质，某些化合物在水中显示出强荧光。