methyl 4-isocyanato-3-(phenylethynyl)benzoate | 1190199-94-0

• 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: methyl 4-isocyanato-3-(phenylethynyl)benzoate
• 英文别名: Methyl 4-isocyanato-3-(2-phenylethynyl)benzoate
• CAS: 1190199-94-0
• 化学式: C₁₇H₁₁NO₃
• 分子量: 277.279
• InChiKey: AYOJUIRPLQQEAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-isocyanato-3-(phenylethynyl)benzoate 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 methyl (Z)-3-(1-chloro-1-phenylmethylidene)-2-oxo-2,3-dihydro-1H-indole-5-carboxylate 、 methyl (E)-3-(1-chloro-1-phenylmethylidene)-2-oxo-2,3-dihydro-1H-indole-5-carboxylate
  参考文献：
  名称：

  Iron Trichloride-Promoted Cyclization of o-Alkynylaryl Isocyanates: Synthesis of 3-(Chloromethylene)oxindoles

  摘要：

  Iron trichloride promotes the cationic cyclization of o-(arylethynyl)aryl isocyanates leading to 3-(arylchloromethylene)oxindoles which can be stereoselectively converted to (2)-3-(aminomethylene)ox in doles under straightforward conditions. When the alkyne is substituted by an alkyl group, activation of the allylic C-H bond also occurs producing 1,2-(dichloroalkylidene)oxindoles.

  DOI：

  10.1021/ol9014877
• 作为产物：
  描述：

  三光气 、 methyl 4-amino-3-(phenylethynyl)benzoate 在 三乙胺 作用下， 以 甲苯 为溶剂， 以83%的产率得到methyl 4-isocyanato-3-(phenylethynyl)benzoate
  参考文献：
  名称：

  Iron Trichloride-Promoted Cyclization of o-Alkynylaryl Isocyanates: Synthesis of 3-(Chloromethylene)oxindoles

  摘要：

  Iron trichloride promotes the cationic cyclization of o-(arylethynyl)aryl isocyanates leading to 3-(arylchloromethylene)oxindoles which can be stereoselectively converted to (2)-3-(aminomethylene)ox in doles under straightforward conditions. When the alkyne is substituted by an alkyl group, activation of the allylic C-H bond also occurs producing 1,2-(dichloroalkylidene)oxindoles.

  DOI：

  10.1021/ol9014877

文献信息

• Indolinone derivatives as inhibitors of maternal embryonic leucine zipper kinase
  申请人：BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM

  公开号：US10981896B2

  公开（公告）日：2021-04-20

  The present disclosure relates to indolinone compounds, compositions, and methods for the inhibition of maternal embryonic leucine zipper kinase (MELK). The present disclosure further relates to indolinone compounds, compositions, and methods for the treatment or prevention of a cancer (for example, triple negative breast cancer). Disclosed herein are compounds according to Formula I:

  本公开涉及用于抑制母体胚胎亮氨酸拉链激酶（MELK）的吲哚啉酮化合物、组合物和方法。本公开进一步涉及用于治疗或预防癌症（例如三阴性乳腺癌）的吲哚啉酮化合物、组合物和方法。本文公开了根据式 I 的化合物：
• INDOLINONE DERIVATIVES AS INHIBITORS OF MATERNAL EMBRYONIC LEUCINE ZIPPER KINASE
  申请人：BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM

  公开号：US20210317107A1

  公开（公告）日：2021-10-14

  The present disclosure relates to indolinone compounds, compositions, and methods for the inhibition of maternal embryonic leucine zipper kinase (MELK). The present disclosure further relates to indolinone compounds, compositions, and methods for the treatment or prevention of a cancer (for example, triple negative breast cancer).