3-{1-[4-(trifluoromethyl)phenyl]prop-2-en-1-yl}-1H-indole | 1021941-49-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-{1-[4-(trifluoromethyl)phenyl]prop-2-en-1-yl}-1H-indole
• 英文别名: 3-(1-(4-(trifluoromethyl)phenyl)allyl)-1H-indole；3-[1-[4-(trifluoromethyl)phenyl]prop-2-enyl]-1H-indole
• CAS: 1021941-49-0；1186369-17-4；1620878-83-2
• 化学式: C₁₈H₁₄F₃N
• 分子量: 301.311
• InChiKey: DFBIEWLDRNUQJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 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：
  3

反应信息

• 作为产物：
  描述：

  对三氟甲基苯甲醛 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 3-{1-[4-(trifluoromethyl)phenyl]prop-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 Enantioselective Intermolecular Indole C2‐Allylation
  作者：James A. Rossi‐Ashton、Aimee K. Clarke、James R. Donald、Chao Zheng、Richard J. K. Taylor、William P. Unsworth、Shu‐Li You

  DOI：10.1002/anie.202001956

  日期：2020.5.4

  The enantioselective intermolecular C2-allylation of 3-substituted indoles is reported for the first time. This directing group-free approach relies on a chiral Ir-(P, olefin) complex and Mg(ClO4 )2 Lewis acid catalyst system to promote allylic substitution, providing the C2-allylated products in typically high yields (40-99 %) and enantioselectivities (83-99 % ee) with excellent regiocontrol. Experimental

  首次报道了3-取代吲哚的对映选择性分子间C2-烯丙基化。这种无导向基团的方法依赖于手性 Ir-(P, 烯烃) 配合物和 Mg(ClO4 )2 Lewis 酸催化剂系统来促进烯丙基取代，以通常高收率 (40-99%) 提供 C2 烯丙基化产物，并且对映选择性 (83-99 % ee) 和出色的区域控制。实验研究和 DFT 计算表明，该反应通过直接 C2 烯丙基化进行，而不是先进行 C3 烯丙基化，然后进行原位迁移。吲哚-C3 位置的空间拥挤和改进的 π-π 堆积相互作用已被确定为 C2 选择性的主要贡献者。
• Ir-Catalyzed Regio- and Enantioselective Friedel–Crafts-Type Allylic Alkylation of Indoles
  作者：Wen-Bo Liu、Hu He、Li-Xin Dai、Shu-Li You

  DOI：10.1021/ol800409d

  日期：2008.5.1

  Highly regio- and enantioselective Ir-catalyzed Friedel-Crafts type allylic alkylation of indoles have been realized using [Ir(COD)Cl]2/phosphoramidite ligand 1a, affording the branched products with up to >97/3 branched-linear ratio and 92% ee.

  使用[Ir（COD）Cl] 2 /亚磷酰胺配体1a已经实现了吲哚的高度区域选择性和对映选择性的Ir催化的Friedel-Crafts型烯丙基烷基化，提供的支链产物的支链线性比高达> 97/3，而92 ％ee。
• 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.