5-fluoro-4,7-dihydro-1H-indole | 1039170-79-0

• 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: 5-fluoro-4,7-dihydro-1H-indole
• 英文别名: 5-fluoro-4,7-dihydroindole
• CAS: 1039170-79-0
• 化学式: C₈H₈FN
• 分子量: 137.157
• InChiKey: AXQQAVKVLGDREW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-fluoro-4,7-dihydro-1H-indole 、 N-亚苄基-4-甲基苯磺酰胺 在 (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以83%的产率得到N-((5-fluoro-4,7-dihydro-1H-indol-2-yl)(phenyl)methyl)-4-methyllbenzenesulfonamide
  参考文献：
  名称：

  4,7-二氢吲哚与亚胺通过手性磷酸的高度对映选择性的friedel-crafts反应：容易获得2-吲哚基甲胺衍生物。

  摘要：

  DOI：

  10.1002/chem.200800263

文献信息

• Asymmetric Friedel-Crafts Reaction of 4,7-Dihydroindoles with Nitroolefins by Chiral Brønsted Acids under Low Catalyst Loading
  作者：Yi-Fei Sheng、Gong-Qiang Li、Qiang Kang、An-Jiang Zhang、Shu-Li You

  DOI：10.1002/chem.200900033

  日期：2009.3.23

  Slowly does it! By adding the substrate by a syringe pump, a highly efficient Friedel–Crafts reaction of 4,7‐dihydroindoles with nitroolefins was realized with 0.5 mol % of a chiral phosphoric acid. The Friedel–Crafts alkylation, together with a subsequent oxidation of the product, led to 2‐substituted indoles in excellent enantiomeric excesses, which can be easily transformed to enantioenriched t

  慢慢来！通过使用注射泵添加底物，可以用0.5 mol％的手性磷酸实现4,7-二氢吲哚与硝基烯烃的高效Friedel-Crafts反应。Friedel-Crafts烷基化反应以及随后的产物氧化，导致对映异构体过量存在的2个取代的吲哚，很容易转化为对映体富集的四氢-γ-咔啉。
• Enantioselective Friedel-Crafts Alkylation of 4,7-Dihydroindoles with Enones Catalyzed by Primary-Secondary Diamines
  作者：Liang Hong、Wangsheng Sun、Chunxia Liu、Lei Wang、Kwokyin Wong、Rui Wang

  DOI：10.1002/chem.200901635

  日期：2009.10.26

  selectivity: A primary–secondary diamine catalyst 1 was readily prepared from a commercially available amino acid and has been applied in the asymmetric Friedel–Crafts alkylation of 4,7‐dihydroindoles with α,β‐unsaturated enones. A series of aromatic, aliphatic, and cyclic α,β‐unsaturated ketones can be converted into the desired products in moderate to high yields with excellent enantioselectivities (up to

  优异的选择性：伯-仲二胺催化剂1易于从市售氨基酸制备，并已用于4,7-二氢吲哚与α，β-不饱和烯酮的不对称Friedel-Crafts烷基化反应。在温和条件下，一系列芳族，脂肪族和环状α，β-不饱和酮可以中等至高收率转化成所需的产品，并具有出色的对映选择性（最高97％ee）。
• Asymmetric Allylic Alkylation of Pyrroles and 4,7-Dihydroindoles with Alkene–Phosphine Ligands
  作者：Yilin Liu、Ziping Cao、Haifeng Du

  DOI：10.1021/jo300539y

  日期：2012.5.4

  A palladium-catalyzed highly enantioselective allylic alkylation of pyrroles and 4,7-dihydroindoles has been successfully developed with the use of chiral alkene-phosphine hybrid ligands to furnish the desired products in high yields with excellent ee's. It is noteworthy that alkene-phosphine ligands are much more effective than some other types of chiral ligands in this catalytic system.
• Highly Enantioselective Friedel–Crafts Reaction of 4,7-Dihydroindoles with Imines by Chiral Phosphoric Acids: Facile Access to 2-Indolyl Methanamine Derivatives
  作者：Qiang Kang、Xiao-Jian Zheng、Shu-Li You

  DOI：10.1002/chem.200800263

  日期：2008.4.18