1-methyl-3-(4-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one

• 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: 1-methyl-3-(4-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one
• 英文别名: (3E)-1-methyl-3-[[4-(trifluoromethyl)phenyl]methylidene]indol-2-one
• 化学式: C₁₇H₁₂F₃NO
• 分子量: 303.284
• InChiKey: JMEQDBYIHRWSII-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯甲酰甲酸甲酯 、 1-methyl-3-(4-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one 在 三(二甲胺基)膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 dimethyl 2,3-diphenyloxirane-2,3-dicarboxylate 、 methyl 1'-methyl-2'-oxo-2-phenyl-3-(4-(trifluoromethyl)phenyl)spiro[cyclopropane-1,3'-indoline]-2-carboxylate 、 methyl 1'-methyl-2'-oxo-2-phenyl-3-(4-(trifluoromethyl)phenyl)spiro[cyclopropane-1,3'-indoline]-2-carboxylate 、 methyl 1'-methyl-2'-oxo-2-phenyl-3-(4-(trifluoromethyl)phenyl)spiro[cyclopropane-1,3'-indoline]-2-carboxylate
  参考文献：
  名称：

  Stereochemical implications in the synthesis of 3,3′-spirocyclopropyl oxindoles from β-aryl/alkyl-substituted alkylidene oxindoles

  摘要：

  3,3'-Spirocyclopropane oxindoles were synthesized in good to excellent yield and diastereoselectivity employing a Kukhtin Ramirez reaction between readily accessible E-alkylidene oxindoles, commercially available P(NMe2)(3), and alpha-keto esters. The stereoselectivity in the cyclopropanation event can be traced to the starting alkylidene geometry and the propensity of the exocyclic alkene to undergo isomerization in the presence of an electron rich phosphine. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.004
• 作为产物：
  描述：

  [(methyl-phenyl-carbamoyl)-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-methyl]-phosphonic acid diethyl ester 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.13h， 生成 1-methyl-3-(4-trifluoromethyl-benzylidene)-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  One-Pot Homolytic Aromatic Substitutions/HWE Olefinations under Microwave Conditions for the Formation of a Small Oxindole Library

  摘要：

  An efficient one-pot sequence comprising a homolytic aromatic substitution followed by an ionic Horner-Wadsworth-Emmons olefination for the preparation of a small library of alpha,beta-unsaturated oxindoles is presented. Microwave-induced heating is used to conduct these reactions. The homolytic aromatic substitution is mediated by the persistent radical effect.

  DOI：

  10.1021/ol048759t

文献信息

• Tandem Horner–Wadsworth–Emmons/Heck procedures for the preparation of 3-alkenyl-oxindoles: the synthesis of Semaxanib and GW441756
  作者：Jana Lubkoll、Alessia Millemaggi、Alexis Perry、Richard J.K. Taylor

  DOI：10.1016/j.tet.2010.03.018

  日期：2010.8

  developed to provide rapid access to 3-alkenyl-oxindoles from α-halo-anilides. This one-pot microwave accelerated process proceeds with catalytic palladium(II) acetate or tetrakis(triphenylphosphine)palladium, and has been used to prepare a range of adducts derived from aromatic, heteroaromatic and aliphatic aldehydes. The procedures can be used to prepare N-unprotected oxindoles directly and the applicability

  已经开发了一个串联序列，涉及霍纳-沃兹沃思-埃蒙斯（HWE）烯化反应，然后进行钯催化的分子内Heck反应，以提供从α-卤代苯胺快速获得3-烯基-氧吲哚的途径。这种一锅微波加速方法是使用乙酸乙酸钯（II）或四（三苯基膦）钯催化的，已用于制备一系列衍生自芳族，杂芳族和脂族醛的加合物。该方法可用于直接制备N-未保护的羟吲哚，并且该方法的适用性通过一锅合成塞马克尼（一种血管生成信号抑制剂）和GW441756（一种氮杂-羟吲哚Trk A抑制剂）来建立。