2-(5-chloro-2-methylphenyl)isoindoline-1,3-dione | 57023-60-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(5-chloro-2-methylphenyl)isoindoline-1,3-dione
• 英文别名: 2-(5-Chloro-2-methylphenyl)isoindole-1,3-dione
• CAS: 57023-60-6
• 化学式: C₁₅H₁₀ClNO₂
• 分子量: 271.703
• InChiKey: IPLDTFGONDBSSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-chloro-2-methylphenyl)isoindoline-1,3-dione 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 30.0h， 生成 3-chloro-6H-isoindolo[2,1-a]indol-6-one
  参考文献：
  名称：

  Synthesis and biological activity of 6H-isoindolo[2,1-a]indol-6-ones, analogues of batracylin, and related compounds

  摘要：

  Closely related to batracylin, 6H-isoindolo[2,1-a]indol-6-ones including 2-nitro- 13a, 2-amino- 14, and 2-diethylaminopropionamide derivative 16 as well as D-ring substituted 13b, 13c or A-ring substituted 13d and 20 analogues, were synthesised and evaluated against L1210 leukaemia. Subsequent treatment of 13b and 13c with NN-diethylethylenediarnine at 180 degrees C, led to compounds 17a and 17b arising from an unexpected opening of the pyrrolidinone ring and amidification of the keto group. Under the same conditions, the dichloro derivative 13d led to the monoalkyl compound 20 which was the most cytotoxic of the series. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.008
• 作为产物：
  描述：

  苯酐 、 5-氯邻甲苯胺 在 phthalimide-N-sulfonic acid 作用下， 以 乙醇 为溶剂， 以86%的产率得到2-(5-chloro-2-methylphenyl)isoindoline-1,3-dione
  参考文献：
  名称：

  非手性邻苯二甲酰亚胺结晶诱导脱消旋不对称合成二氢吲哚

  摘要：

  不对称合成是通过结合非手性底物的光化学反应，然后是结晶诱导的去消旋化来进行的。通过 N-(5-氯-2-甲基苯基)邻苯二甲酰亚胺的光化学分子内 δ-氢提取和环化反应产生的稠合二氢吲哚结晶为外消旋聚集体，并通过 Viedma 熟化进行结晶诱导去外消旋，对映选择性为 99 % ee。这是第一个通过光化学夺氢反应和结晶诱导去消旋进行不对称表达和放大的例子。

  DOI：

  10.1002/chem.202103345

文献信息

• Direct C–H amination reactions of arenes with <i>N</i>-hydroxyphthalimides catalyzed by cuprous bromide
  作者：Dongming Zhang、Bin Lv、Pan Gao、Xiaodong Jia、Yu Yuan

  DOI：10.3762/bjoc.18.65

  日期：——

  An efficient Cu-catalyzed strategy for the direct C–H amination of arenes in high yields using N-hydroxyphthalimide as the amidyl radical precursor under air is reported. A possible mechanism is proposed that proceeds via a radical reaction in the presence of CuBr and triethyl phosphite.

  报道了一种使用N-羟基邻苯二甲酰亚胺作为酰胺基自由基前体在空气下以高产率直接 C-H 胺化芳烃的有效 Cu 催化策略。提出了一种可能的机制，即在 CuBr 和亚磷酸三乙酯存在下通过自由基反应进行。
• DE668743
  申请人：——

  公开号：——

  公开（公告）日：——
• US2087715
  申请人：——

  公开号：——

  公开（公告）日：——
• Photocatalytic C–H Activation and Amination of Arenes with Nonactivated <i>N</i>-Hydroxyphthalimides Involving Phosphine-Mediated N–O Bond Scission
  作者：Zhentao Pan、Bo Chen、Jingxi Fang、Tong Liu、Jiayao Fang、Yongmin Ma

  DOI：10.1021/acs.joc.2c01975

  日期：2022.11.4
• Synthesis and biological activity of 6H-isoindolo[2,1-a]indol-6-ones, analogues of batracylin, and related compounds
  作者：Jean Guillaumel、Stéphane Léonce、Alain Pierré、Pierre Renard、Bruno Pfeiffer、Paola B. Arimondo、Claude Monneret

  DOI：10.1016/j.ejmech.2005.10.008

  日期：2006.3

  Closely related to batracylin, 6H-isoindolo[2,1-a]indol-6-ones including 2-nitro- 13a, 2-amino- 14, and 2-diethylaminopropionamide derivative 16 as well as D-ring substituted 13b, 13c or A-ring substituted 13d and 20 analogues, were synthesised and evaluated against L1210 leukaemia. Subsequent treatment of 13b and 13c with NN-diethylethylenediarnine at 180 degrees C, led to compounds 17a and 17b arising from an unexpected opening of the pyrrolidinone ring and amidification of the keto group. Under the same conditions, the dichloro derivative 13d led to the monoalkyl compound 20 which was the most cytotoxic of the series. (c) 2006 Elsevier SAS. All rights reserved.