5-chloro-3-(2-oxo-2-phenylethylidene)indolin-2-one | 1292780-69-8

• 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: 5-chloro-3-(2-oxo-2-phenylethylidene)indolin-2-one
• CAS: 1292780-69-8
• 化学式: C₁₆H₁₀ClNO₂
• 分子量: 283.714
• InChiKey: GHVCIPVOXSQWSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  5-chloro-3-hydroxy-3-(2-oxo-2-phenylethyl)indolin-2-one 反应 0.13h， 以94%的产率得到5-chloro-3-(2-oxo-2-phenylethylidene)indolin-2-one
  参考文献：
  名称：

  环保型聚乙二醇400作为一种快速有效的可循环利用的反应介质，可用于合成抗癌的伊斯廷连接的查尔酮及其3羟基前体

  摘要：

  Isatin查耳酮及其3-羟基前体被证明具有潜在的抗癌活性，并且还是用于合成多种生物活性螺-羟吲哚的通用底物和关键中间体。已开发出一种环保的串联合成法，使用PEG 400作为绿色溶剂兼相转移催化剂，可用于一系列3-羟基-2-氧吲哚和3-亚甲基-2-氧吲哚。将报告的单罐可持续合成策略与常规方法进行了比较，发现该方法在简便性，产物收率和反应时间方面均优于现有的两步合成方法，并且具有较大的底物范围。

  DOI：

  10.1002/jhet.3424

文献信息

• Diastereoselective trans Cyclopropanation of 3-Alkylidene Oxindoles with In Situ Generated α-Diazo Carbonyls or α,β-Unsaturated Diazo Compounds
  作者：Chhanda Mukhopadhyay、Sayan Pramanik、Suman Ray、Suvendu Maity、Prasanta Ghosh

  DOI：10.1055/a-1384-1967

  日期：2021.7

  An efficient diastereoselective trans cyclopropanation of 3-alkylidene oxindoles with in situ generated α-diazo carbonyl compounds or α,β-unsaturated diazo compounds under metal-free conditions has been developed to synthesize 3-spirocyclopropyl-2-oxindole derivatives. The procedure is based on the 1,3-dipolar character of the corresponding diazo compounds under base-catalyzed conditions. The method has a wide substrate scope and uses easily available starting materials.

  开发了一种高效的立体选择性反式环丙烷化反应，用于合成3-烷基亚基氧化吲哚与现场生成的α-重氮羰基化合物或α,β-不饱和重氮化合物的反应，无需金属条件即可合成3-螺环丙基-2-氧化吲哚衍生物。该方法基于相应重氮化合物在碱催化条件下的1,3-偶极特性。该方法具有广泛的底物范围，并使用易于获得的起始材料。

• Unexpected isocyanide-based cascade cycloaddition reaction with methyleneindolinone
  作者：Jian Li、Shikuan Su、Mengyuan Huang、Boyi Song、Chunju Li、Xueshun Jia

  DOI：10.1039/c3cc46237d

  日期：——

  An unprecedented cascade reaction of isocyanide and methyleneindolinone has been established, which represents a novel and different reaction mode. This present transformation involves the ring-opening of methyleneindolinone and the construction of two other new rings simultaneously in an atom-economic manner.

  已经建立了前所未有的异氰酸酯与亚甲基吲哚酮的级联反应，它代表了一种新颖而又不同的反应模式。该当前的转化涉及以原子经济的方式同时打开亚甲基吲哚酮的开环和同时构建另外两个新的环。
• Access to 3-Prenylated Oxindoles by α-Regioselective Prenylation: Application to the Synthesis of (±)-Debromoflustramine E
  作者：De-Feng Li、Kun Liu、Yi-Xuan Jiang、Yan Gu、Jing-Ru Zhang、Li-Ming Zhao

  DOI：10.1021/acs.orglett.8b00045

  日期：2018.2.16

  development of a rapid, highly efficient, and one-pot synthesis of C3-α-prenylated oxindoles with simple reagents is described. The process is based on zinc-mediated α-regioselective prenylation of 3-acylidene-oxindole with commercially available prenyl bromide using inexpensive CeCl3 as the catalyst. The new transformation tolerates a wide range of 3-acylidene-oxindoles, providing easy access to a variety

  描述了用简单的试剂快速，高效，一锅合成C3-α-戊烯基化的吲哚的方法。该方法基于使用便宜的CeCl 3作为催化剂，用市售的异戊烯基溴与锌介导的3-丙叉基-氧吲哚的α-区域选择性烯丙基化。新的转化方法可耐受各种3-丙炔基-羟吲哚，可轻松获得各种功能化的3-烯丙基化的羟吲哚。该方法的合成效用通过氟他胺家族生物碱（±）-去溴氟胺E的形式合成得到证实。
• Temperature-Dependent Double Isocyanide Insertion Reaction To Construct a Polycyclic Skeleton
  作者：Yaming Tian、Lumin Tian、Chunju Li、Xueshun Jia、Jian Li

  DOI：10.1021/acs.orglett.6b00131

  日期：2016.2.19

  A novel strategy to furnish selective double insertion of isocyanides with the aid of potassium tetrachloroaurate(III) has been disclosed. This strategy provides quick access to approach a complex polycyclic skeleton in an efficient manner. Unexpected oxygen migration was also observed when the reaction was conducted at a lower temperature.

  公开了一种新颖的策略，其借助于四氯金酸钾（III）选择性地双插入异氰酸酯。该策略提供了以有效方式快速访问复杂的多环骨架的途径。当反应在较低温度下进行时，也观察到了意外的氧迁移。
• Molecular diversity of cycloaddition reactions of the functionalized pyridinium salts with 3-phenacylideneoxindoles
  作者：Qin Fu、Chao-Guo Yan

  DOI：10.1016/j.tet.2013.05.034

  日期：2013.7

  cycloaddition reactions of a series of functionalized pyridinium salts, which were generated from reaction of pyridine with active alkyl halides such as p-nitrobenzyl bromide, N,N-diethyl chloroacetamide and phenacyl bromides with 3-phenacylideneoxindoles in the presence of triethylamine showed very interesting molecular diversities. A series of the functionalized spiro[cyclopropane-1,3′-indolines], and 3-

  在三乙胺的存在下，吡啶与活性烷基卤化物（如对硝基苄基溴，N，N-二乙基氯乙酰胺和苯甲酰溴与3-苯乙叉基氧吲哚）反应生成的一系列官能化吡啶鎓盐的环加成反应显示出非常有趣的结果。分子多样性。根据吡啶鎓盐的结构和反应条件，成功制备了一系列官能化的螺[环丙烷-1,3'-二氢吲哚]和3-呋喃-3（2 H）-亚烷基）吲哚-2-酮。简要讨论了反应的区域选择性和立体选择性以及反应机理。