N-[(1H-indol-3yl)(phenyl)methyl]benzenesulfonamide | 1417313-04-2

• 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-[(1H-indol-3yl)(phenyl)methyl]benzenesulfonamide
• 英文别名: N-[indol-3-yl-phenylmethyl]benzenesulfonamide；N-(indol-3-ylphenylmethyl)benzenesulfonamide；N-[(R)-1H-indol-3-yl(phenyl)methyl]benzenesulfonamide
• CAS: 1417313-04-2
• 化学式: C₂₁H₁₈N₂O₂S
• 分子量: 362.452
• InChiKey: JEGPPVPBJITRLC-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  70.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 、 N-苯亚甲基苯磺酰胺 在 3,3’-bis[3,5-bis(perfluoropropan-2-yl)phenyl]-1,1’-binaphthalene-2,2’-sulfonimide 作用下， 以 甲苯 为溶剂， 反应 2.75h， 以93%的产率得到N-[(1H-indol-3yl)(phenyl)methyl]benzenesulfonamide
  参考文献：
  名称：

  手性磺酰亚胺作为布朗斯台德酸有机催化剂用于亚胺与吲哚的不对称Friedel-Crafts烷基化

  摘要：

  首次证明了基于联萘基的手性磺酰亚胺（CSI）在不对称有机催化中是一种有效的强布朗斯台德酸。合成了一系列CSI，并在亚胺与吲哚的不对称Friedel-Crafts烷基化反应中进行了筛选。已经获得了良好至优异的产率和对映选择性。事实证明，在使用前用HCl清洗CSI催化剂至关重要。

  DOI：

  10.1021/jo2011335

文献信息

• Dinuclear zinc catalyzed asymmetric Friedel–Crafts amidoalkylation of indoles with aryl aldimines
  作者：Bei-Lei Wang、Nai-Kai Li、Jin-Xin Zhang、Guo-Gui Liu、Teng Liu、Qi Shen、Xing-Wang Wang

  DOI：10.1039/c0ob01200a

  日期：——

  The asymmetric Friedel–Crafts amidoalkylation of indoles with aryl aldimines could be efficiently catalyzed by Trost's bis-ProPhenol dinuclear zinc complexes to attain 3-indolyl methanamine derivatives in good to excellent yields (85–98%) with moderate to high enantiomeric ratios (from 70 : 30 up to 95 : 5 er). Remarkably, this approach provides efficient access to enantiomerically enriched 3-indolyl

  Trost的双-Pro-Phenol双核锌络合物可以有效地催化吲哚与芳基亚胺的不对称Friedel-Crafts酰胺烷基化反应，从而以中等至高对映体比率（70以上）获得3-吲哚基甲胺衍生物，产率高至优异（85-98％）。 ：30到95：5 er）。值得注意的是，这种方法可以有效地获得对映异构体富集的3-吲哚基甲烷胺，从而避免了不良的双（三）和三（吲哚基）甲烷（BIM和TIM）副产物的形成。
• Cavity-induced enantioselectivity reversal in a chiral metal–organic framework Brønsted acid catalyst
  作者：Min Zheng、Yan Liu、Cheng Wang、Shubin Liu、Wenbin Lin

  DOI：10.1039/c2sc20379k

  日期：——

  A pair of highly porous chiral metal–organic frameworks (CMOFs 1 and 2) were constructed from [Cu2(carboxylate)4] secondary building units (SBUs) and chiral 3,3′,6,6′- or 4,4′,6,6′-tetra(benzoate) ligands derived from 1,1′-binaphthyl-2,2′-phosphoric acid. Both 1 and 2 were active catalysts for Friedel–Crafts reactions between indole and imines. Interestingly, the 1-catalyzed asymmetric reactions yielded the major enantiomers of the opposite chirality to those afforded by the corresponding homogeneous catalyst. Structural analyses and QM/MM calculations revealed that the flip of product handedness results from the chiral environment of CMOF-1 cavity, similar to enzymatic catalysis in which the product stereoselectivity is determined by the enzyme pocket.

  一对高度多孔的手性金属有机框架（CMOF 1 和 2）由 [Cu2(羧酸盐) 4] 二级结构单元 (SBU) 和手性 3,3 , 6,6 或 4 构建而成，衍生自 1,1-联萘-2,2-磷酸的 4-,6,6-四（苯甲酸酯）配体。 1 和 2 都是吲哚和亚胺之间弗里德尔·克拉夫茨反应的活性催化剂。有趣的是，1-催化的不对称反应产生了与相应均相催化剂所提供的手性相反的主要对映体。结构分析和QM/MM计算表明，产物旋向性的翻转是由CMOF-1空腔的手性环境引起的，类似于酶催化中产物的立体选择性由酶袋决定。
• Stepwise fabrication and architecture of heterogeneous 9-thiourea epiquinine catalyst with excellent enantioselectivity in the asymmetric Friedel–Crafts reaction of indoles with imines
  作者：Peng Yu、Jing He、Lan Yang、Min Pu、Xiaodan Guo

  DOI：10.1016/j.jcat.2008.09.006

  日期：2008.11

  Heterogeneous 9-thiourea epiquinine catalysts are prepared by covalently anchoring 9-(3,5-bis(trifluoromethyl)phenylthiourea)epiquinine on mesoporous silica surfaces via mercapto linker. It is found that 9-thiourea epiquinine moieties are located comparably on the interior and exterior surfaces of SBA-15 while preferentially on the exterior surface of MCM-41. The heterogeneous 9-thiourea epiquinine are applied as catalysts in the asymmetric Friedel-Crafts reaction of indoles with imines. SBA-15 supported 9-thiourea epiquinine, with more catalytic sites inside the channels, is found more chemselective and enantioselective than the counterpart supported on MCM-41. The effects of solvents and molecule dimensions of both substrates on the reaction effectiveness and selectivity are also discussed. (C) 2008 Elsevier Inc. All rights reserved.
• SPINOL-Derived Phosphoric Acids: Synthesis and Application in Enantioselective Friedel−Crafts Reaction of Indoles with Imines
  作者：Fangxi Xu、Dan Huang、Chao Han、Wei Shen、Xufeng Lin、Yanguang Wang

  DOI：10.1021/jo101640z

  日期：2010.12.17

  A new class of chiral phosphoric acids with spirobiindane s scaffold were conveniently synthesized from (S)-1,1'-spirobiindane-7,7'-diol ((S)-SPINOL) and employed to catalyze the asymmetric Friedel-Crafts reaction of in-doles with imines to afford 3-indolylmethanamines. High yields (68-97%) and excellent enantioselectivities (up to 99% ee) were obtained.
• Chiral Sulfonimide as a Brønsted Acid Organocatalyst for Asymmetric Friedel–Crafts Alkylation of Indoles with Imines
  作者：Ling-Yan Chen、Hao He、Wing-Hong Chan、Albert W. M. Lee

  DOI：10.1021/jo2011335

  日期：2011.9.2

  Binaphthyl-based chiral sulfonimide (CSI) is demonstrated for the first time to be an efficient, strong Brønsted acid in asymmetric organocatalysis. A series of CSIs were synthesized and screened in the asymmetric Friedel–Crafts alkylation of indoles with imines. Good to excellent yields and enantioselectivities have been achieved. It was proved that it was crucial to wash the CSI catalyst with HCl

  首次证明了基于联萘基的手性磺酰亚胺（CSI）在不对称有机催化中是一种有效的强布朗斯台德酸。合成了一系列CSI，并在亚胺与吲哚的不对称Friedel-Crafts烷基化反应中进行了筛选。已经获得了良好至优异的产率和对映选择性。事实证明，在使用前用HCl清洗CSI催化剂至关重要。