3'-benzoyl-5-chlorospiro[indoline-3,2'-oxiran]-2-one | 1217043-09-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'-benzoyl-5-chlorospiro[indoline-3,2'-oxiran]-2-one
• 英文别名: 3'-benzoyl-5-chlorospiro[1H-indole-3,2'-oxirane]-2-one
• CAS: 1217043-09-8
• 化学式: C₁₆H₁₀ClNO₃
• 分子量: 299.713
• InChiKey: HBGQEQLHAJVYHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3'-benzoyl-5-chlorospiro[indoline-3,2'-oxiran]-2-one 、 硫代乙酰胺 在 lithium bromide 作用下， 以 水 为溶剂， 反应 0.1h， 以87%的产率得到2'-amino-4'-benzoyl-5-chloro-2'-methylspiro[indoline-3,5'-[1,3]oxathiolan]-2-one
  参考文献：
  名称：

  Ultrasound promoted greener synthesis of spiro[indole-3,5′-[1,3]oxathiolanes in water

  摘要：

  An aqueous mediated novel synthesis of substituted 2'amino-4'benzoyl-2'-methyl spiro[indole 3,5'-[1,3]oxathiolane]-2(1H)-ones (2a-f) was carried out from the reaction of spiro [indole-3,2'-oxiranes] (1a-f) with thioacetamide in the presence of LiBr as catalyst. The reaction was carried out under both microwaves and sonication and results were also compared with conventional method. in general, improvement in rate and yields observed when reaction was carried out under sonication as compared to microwave irradiation and conventional method. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2009.08.003
• 作为产物：
  描述：

  5-chloro-3-(2-oxo-2-phenylethylidene)indolin-2-one 在 双氧水 作用下， 生成 3'-benzoyl-5-chlorospiro[indoline-3,2'-oxiran]-2-one
  参考文献：
  名称：

  Ultrasound promoted greener synthesis of spiro[indole-3,5′-[1,3]oxathiolanes in water

  摘要：

  An aqueous mediated novel synthesis of substituted 2'amino-4'benzoyl-2'-methyl spiro[indole 3,5'-[1,3]oxathiolane]-2(1H)-ones (2a-f) was carried out from the reaction of spiro [indole-3,2'-oxiranes] (1a-f) with thioacetamide in the presence of LiBr as catalyst. The reaction was carried out under both microwaves and sonication and results were also compared with conventional method. in general, improvement in rate and yields observed when reaction was carried out under sonication as compared to microwave irradiation and conventional method. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2009.08.003

文献信息

• Facile synthesis of functionalized spiro[indoline-3,2'-oxiran]-2-ones by Darzens reaction
  作者：Qin Fu、Chao-Guo Yan

  DOI：10.3762/bjoc.9.105

  日期：——

  A series of functionalized spiro[indoline-3,2'-oxiran]-2-ones was efficiently synthesized by Darzens reaction of phenacyl bromides with isatins both with N-alkyl groups and without N-substituent in the presence of potassium carbonate as a base catalyst. When two equivalents phenacyl bromides were used in the reaction, the N-substitution reaction of isatin also finished with the formation of spiro-oxirane-oxindoles.

  一系列功能化的螺环[吲哚啉-3,2'-环氧]-2-酮通过在钾碳酸盐存在下的苯乙酰溴与带有和不带有N-烷基基团的吲哚啉进行Darzens反应而高效合成。当在反应中使用两当量苯乙酰溴时，也完成了吲哚啉的N-取代反应，形成螺环氧环氧吲哚酮。