N-(5-methoxy-indol-3-yl-phenylmethyl)-4-methylbenzenesulfonamide | 929050-90-8

• 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-(5-methoxy-indol-3-yl-phenylmethyl)-4-methylbenzenesulfonamide
• 英文别名: N-[(R)-(5-methoxy-1H-indol-3-yl)-phenylmethyl]-4-methylbenzenesulfonamide
• CAS: 929050-90-8
• 化学式: C₂₃H₂₂N₂O₃S
• 分子量: 406.505
• InChiKey: RORBRKCNQOOKFP-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  79.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 、 N-亚苄基-4-甲基苯磺酰胺 在 3-[[3,5-双（三氟甲基）苯基]氨基]-4-[[（（1R，2R）-2-（二甲基氨基）环己基]氨基]-3-环丁烯-1,2-二酮 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以96%的产率得到N-(5-methoxy-indol-3-yl-phenylmethyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Squaramide-catalyzed enantioselective Friedel–Crafts reaction of indoles with imines

  摘要：

  手性方酰胺是吲哚与 N-对甲苯磺酰亚胺进行 FriedelâCrafts 反应的高对映选择性催化剂，可生成 3-吲哚基甲胺产品，收率 85â96% ，醚率 84â96% 。

  DOI：

  10.1039/b922120d

文献信息

• 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。
• Synthesis and application of the first planar chiral strong brønsted acid organocatalysts
  作者：Dieter Enders、Monika Ludwig、Gerhard Raabe

  DOI：10.1002/chir.21985

  日期：2012.3

  of planar chiral strong Brønsted acid organocatalysts derived from [2.2]paracyclophane is described. Resolution was accomplished according to a modified protocol involving pseudo‐ortho‐substituted [2.2]paracyclophane‐based sulfoxides for the synthesis of three new sulfonic acids. The first planar chiral phosphoric acid diester was obtained from the corresponding phenyl‐substituted diol derived from

  描述了衍生自[2.2]对环环烷的平面手性强布朗斯台德酸有机催化剂的合成。拆分是根据修改后的规程完成的，该规程涉及用于合成三种新磺酸的基于伪邻位取代的[2.2]对环硫基的亚砜。第一个平面手性磷酸二酯是从对映纯的4-溴-12-羟基[2.2]对环环烷衍生的相应的苯基取代的二醇中获得的。这些新型催化剂在对映选择性Friedel-Crafts反应以及直接不对称Mannich反应中进行了测试，产率高达93％，ee值高达38％。手性，2012年。©2012 Wiley Periodicals，Inc.。
• 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.