N-((4-fluorophenyl)(1H-indol-3-yl)methyl)-4-methylbenzenesulfonamide | 1148116-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((4-fluorophenyl)(1H-indol-3-yl)methyl)-4-methylbenzenesulfonamide
• 英文别名: N-[indol-3-yl-(4-fluorophenyl)methyl]-4-methylbenzenesulfonamide；N-[(4-fluorophenyl)-(1H-indol-3-yl)methyl]-4-methylbenzenesulfonamide
• CAS: 1148116-19-1；1148116-20-4；1332481-01-2
• 化学式: C₂₂H₁₉FN₂O₂S
• 分子量: 394.469
• InChiKey: FJWAGCFUYFNEEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对氟苯甲醛 、 对甲苯磺酰胺 在 硅酸四乙酯 、 亚磷酸二甲酯 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 N-((4-fluorophenyl)(1H-indol-3-yl)methyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Organic hydrogen phosphites and hydrogen phosphates catalyzed Friedel–Crafts amidoalkylation of indoles with aryl aldimines

  摘要：

  A highly efficient and selective Friedel-Crafts amidoalkylation reaction of indoles with N-Ts aryl aldimines has been developed utilizing dimethyl hydrogen phosphite or diphenyl hydrogen phosphate as the organocatalysts, providing a facile and cost-effective process for synthesis of 3-indolyl methanamine derivatives in good to excellent yields. This transformation displays a broad substrate scope and wide functional-group tolerability, regardless of the electronic and steric properties of N-Ts aryl aldimines. Given that the developed catalytic Friedel-Crafts amidoalkylation reaction exhibits several salient features such as metal-free catalysis, high efficiency, low cost and mild reaction condition, this process might have practical applications in the synthesis of 3-indolyl methanamine derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.010

文献信息

• Access to Chiral Bisphenol Ligands (BPOL) through Desymmetrizing Asymmetric Ortho-Selective Halogenation
  作者：Xiaodong Xiong、Tianyu Zheng、Xinyan Wang、Ying-Lung Steve Tse、Ying-Yeung Yeung

  DOI：10.1016/j.chempr.2020.01.009

  日期：2020.4

  Privileged chiral catalyst scaffolds are highly useful in chemical synthesis such as drug preparation. Substituted phenol ligands are among the most frequently used scaffolds. However, the preparation of chiral phenol ligands commonly involves tedious synthetic procedures. Herein, we describe a facile strategy to prepare potent chiral bisphenols (BPOLs) through the desymmetrizing asymmetric ortho-halogenation

  特权手性催化剂支架在化学合成（例如药物制备）中非常有用。取代的酚配体是最常用的支架之一。但是，手性酚配体的制备通常涉及繁琐的合成程序。本文中，我们描述了一种通过去对称不对称邻位卤化制备有效手性双酚（BPOL）的简便策略。为了阐明机械原理，进行了理论和实验研究。操作BPOL产品中的卤素手柄可产生不对称的手性BPOL配体，该配体是潜在的优先催化剂支架，已应用于其他不对称催化反应中。
• Highly enantioselective Friedel–Crafts reaction of indoles with N-sulfonyl aldimines catalyzed by heteroarylidene malonate-type bis(oxazoline) copper(II) complexes
  作者：Lei Liu、Qiuying Zhao、Fengpei Du、Hongliang Chen、Zhaohai Qin、Bin Fu

  DOI：10.1016/j.tetasy.2011.10.017

  日期：2011.11

  The enantioselective Friedel–Crafts addition of indoles to N-sulfonyl aldimines was studied using a heteroarylidene malonate-type bis(oxazoline) as a chiral ligand. High to excellent enantioselectivities (up to >99% ee) were achieved using the complex of copper(II)–L1b with a benzyl group. The effects of ligand structure, solvent, temperature and substrate on the reaction were also investigated.

  使用杂芳基丙二酸酯型双（恶唑啉）作为手性配体，研究了吲哚向N-磺酰基醛亚胺中的吲哚的对映选择性Friedel-Crafts加成反应。使用铜（II）–L1b与苄基的配合物可实现高至优异的对映选择性（高达> 99％ee）。还研究了配体结构，溶剂，温度和底物对反应的影响。
• Efficient chirality switching in the asymmetric addition of indole to N-tosylarylimines in the presence of axially chiral cyclometalated bidentate N-heterocyclic carbene palladium(II) complexes
  作者：Zhen Liu、Min Shi

  DOI：10.1016/j.tetasy.2008.11.015

  日期：2009.1

  Efficient dual stereocontrol can be achieved by using axially chiral cyclometalated bidentate N-heterocyclic carbene palladium(II) complexes for the addition of indole to N-tosylarylimines simply by the adjustment of the R group on the benzene rings of the NHC-Pd(II) complexes. (C) 2008 Elsevier Ltd. All rights reserved.