(E)-3-chloromethylene-indolin-2-one | 67520-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-3-chloromethylene-indolin-2-one
• 英文别名: 3-chloromethylene-1,3-dihydro-indol-2-one；3-chloromethylene-indolin-2-one；3-Chlormethylen-indolin-2-on；E-3-Chlormethylen-indol-2-on；(3E)-3-(chloromethylidene)-1H-indol-2-one
• CAS: 67520-85-8
• 化学式: C₉H₆ClNO
• 分子量: 179.606
• InChiKey: GXYRSFSDNHEUNL-FNORWQNLSA-N

物化性质

• 沸点：
  366.0±42.0 °C(Predicted)
• 密度：
  1.458±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-chloromethylene-indolin-2-one 在 乙醇 、 氨 作用下， 生成 3-aminomethylene-indolin-2-one
  参考文献：
  名称：

  3-Hydroxymethyleneoxindole and its Derivatives

  摘要：

  DOI：

  10.1021/ja01523a068
• 作为产物：
  描述：

  2-氧代吲哚啉-3-甲醛 在 氯化亚砜 作用下， 生成 (E)-3-chloromethylene-indolin-2-one
  参考文献：
  名称：

  Behringer; Weissauer, Chemische Berichte, 1952, vol. 85, p. 743,749

  摘要：

  DOI：

文献信息

• Synthesis and antiproliferative activities of indolin-2-one derivatives bearing amino acid moieties
  作者：Mathieu Sassatelli、Éric Debiton、Bettina Aboab、Michelle Prudhomme、Pascale Moreau

  DOI：10.1016/j.ejmech.2006.03.021

  日期：2006.6

  A convenient synthesis of indolin-2-ones substituted in the 3 position by an aminomethylene group bearing different amino acid moieties is described. Their antiproliferative activities were evaluated toward a panel of human solid tumor cell lines (PC 3, DLD-1, MCF-7, M4 Beu, A549, PA 1) and healthy cell lines (a murine fibroblast L929 and a human fibroblast primary culture).

  描述了在3位上被带有不同氨基酸部分的氨基亚甲基取代的吲哚-2-酮的方便合成。对一组人实体瘤细胞系（PC 3，DLD-1，MCF-7，M4 Beu，A549，PA 1）和健康细胞系（鼠成纤维细胞L929和人成纤维细胞原代培养物）评估了它们的抗增殖活性。
• New indole derivatives. Synthesis of 3-acyl-1-carbethoxy-2-trifluoromethanesulfonylindoles and of substituted 2-vinylindoles
  作者：Egle M Beccalli、Alessandro Marchesini

  DOI：10.1016/0040-4020(94)01092-e

  日期：1995.2

  3-Acyl-1-carbethoxy-2-trifluoromethanesulfonylindoles 6 and 3-acyl-2-vinylindoles 7 are synthesized from 3-[(1-chloro)alkylidene]indol-2(3H)-ones 2 via 1-carbethoxy-3-[(1-dimethylamino)alkylidene]indol-2(3H)-ones 4.
• 6-Chloro-spirocyclohexenindol-2-ones: an unusual ring transformation to ethyl 2-(cyclohexa-1,4-dienyl)phenylcarbamates
  作者：Egle Maria Beccalli、Francesca Clerici、Maria Luisa Gelmi

  DOI：10.1016/s0040-4020(99)00475-5

  日期：1999.7

  The Diels-Alder cycloaddition reaction of 3-chloromethylen-2-indolones 1 with a series of dienes 2 was studied in order to synthesize spirocyclohexenindolones 3 and 4. The reaction proceeded with good diastereoselectivity and regioselectivity. Chloro spirocyclohexenindolones 3 and 4 were transformed into 2-aminobiphenyl derivatives 5 by reacting with sodium ethoxide. Starting from the indolone 1c and 2,3-dimethylbutadiene the spiro compounds 3f and 4e were obtained. On treatment with sodium ethoxide, 3f was transformed into the phenanthridone derivatives 7 and 8. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.