1-benzyl-6-chloroindolin-2,3-dione | 1017609-56-1

• 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: 1-benzyl-6-chloroindolin-2,3-dione
• 英文别名: 1-benzyl-6-chloroindoline-2,3-dione；N-benzyl-6-chloroisatin；1-benzyl-6-chloroindole-2,3-dione
• CAS: 1017609-56-1
• 化学式: C₁₅H₁₀ClNO₂
• 分子量: 271.703
• InChiKey: TWZDTEUOBGXCQU-UHFFFAOYSA-N

物化性质

• 熔点：
  173-174 °C(Solv: ethanol (64-17-5))
• 沸点：
  460.3±55.0 °C(Predicted)
• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 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：

  1-benzyl-6-chloroindolin-2,3-dione 在 silver trifluoromethanesulfonate 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1'-benzyl-6'-chloro-3-(3,5-dimethyl-1H-pyrazol-1-yl)-1,3-diphenylspiro[azetidine-2,3'-indoline]-2',4-dione
  参考文献：
  名称：

  Silver-catalyzed pyrazole migration and cycloaddition reaction of diazo pyrazoleamides with ketimines

  摘要：

  银催化的吡唑迁移和环化反应以高产率和非对映选择性的底物依赖方式得到了很好的证实。

  DOI：

  10.1039/d3cc03253a
• 作为产物：
  描述：

  3-氯苯胺 在 盐酸 、 盐酸羟胺 、 四丁基溴化铵 、 potassium carbonate 、 sodium sulfate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.08h， 生成 1-benzyl-6-chloroindolin-2,3-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of 5′-phenyl-3′H-spiro-[indoline-3,2′-[1,3,4]oxadiazol]-2-one analogs

  摘要：

  A series of 5'-phenyl-3'H-spiro[indoline-3,2'-[1,3,4]thiadiazol]-2-one analogs were synthesized and their Bcl-2 protein inhibitory activities were studied. The lead compound was originally identified using a fluorescence polarization-based competitive binding assay. Among the 10 compounds investigated, 1k showed good binding affinities to Bcl-xL and Mcl-1, with inhibition constants of 8.9 mu mol/L and 3.4 mu mol/L, respectively. While compound 1c achieved tight binding affinities to Bcl-xL (Ki = 0.16 mu mol/L), has the potential to be a new lead compound. (C) 2013 De-Cai Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.06.001

文献信息

• Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole‐4,5‐Diones and Indoline‐2,3‐Diones
  作者：Rong‐Hui Wang、Ya‐Ling Li、Hong‐Jiao He、You‐Cai Xiao、Fen‐Er Chen

  DOI：10.1002/chem.202005081

  日期：2021.3

  The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin‐4,5‐diones and isatins have been developed. In the presence of morpholine‐containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes

  已经开发了对环二酮（包括吡唑啉-4,5-二酮和靛红）的催化对映选择性二有机锌。在含有吗啉的手性氨基醇配体存在的情况下，相应的手性环状叔醇以良好至极佳的收率（高达97％）和对映选择性（高达95％ee）生产。该方案的显着特征包括温和的反应条件，无路易斯酸添加剂和宽泛的官能团耐受性。
• Scope, Limitations and Mechanistic Analysis of the HyperBTM‐Catalyzed Acylative Kinetic Resolution of Tertiary Heterocyclic Alcohols**
  作者：Samuel M. Smith、Mark D. Greenhalgh、Taisiia Feoktistova、Daniel M. Walden、James E. Taylor、David B. Cordes、Alexandra M. Z. Slawin、Paul Ha‐Yeon Cheong、Andrew D. Smith

  DOI：10.1002/ejoc.202101111

  日期：2022.1.11

  isothiourea HyperBTM catalyzes the acylative kinetic resolution of a wide range of tertiary heterocyclic alcohols under mild conditions with high selectivity. The synthetic utility of the methodology has been demonstrated with the preparation of two bioactive targets. Kinetic analysis reveals a fractional reaction order with respect to the alcohol concentration.

  异硫脲 HyperBTM 在温和条件下以高选择性催化多种叔杂环醇的酰化动力学拆分。该方法的合成效用已通过制备两个生物活性靶标得到证明。动力学分析揭示了关于醇浓度的分级反应顺序。
• Carbene‐Catalyzed Enantioselective Aromatic N‐Nucleophilic Addition of Heteroarenes to Ketones
  作者：Yonggui Liu、Guoyong Luo、Xing Yang、Shichun Jiang、Wei Xue、Yonggui Robin Chi、Zhichao Jin

  DOI：10.1002/anie.201912160

  日期：2020.1.2

  and optical purities. Our reaction involves the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibit excellent antibacterial activities against Ralstonia solanacearum (Rs) and

  杂芳基醛的芳族氮原子被卡宾催化剂活化以与酮亲电子试剂反应。以良好至优异的产率和光学纯度提供多功能的环状N，O-乙缩醛产物。我们的反应涉及空前的氮杂富烯型酰基唑鎓中间体的形成。各种各样的N-杂芳族醛和缺电子的酮底物可以有效地实现这种转化。通过该协议提供的几种手性N，O-乙缩醛产品表现出优异的抗青枯菌（Rsstonia solanacearum）的抗菌活性，在开发用于植物保护的新型农业化学品中具有重要的价值。
• 2,2-Difluoro-1,3-diketones as <i>gem</i> -Difluoroenolate Precusors for Asymmetric Aldol Addition with <i>N</i> -Benzylisatins
  作者：Jinlong Qian、Wenbin Yi、Xin Huang、Jerry P. Jasinski、Wei Zhang

  DOI：10.1002/adsc.201600392

  日期：2016.9.1

  2,2‐Difluoro‐1,3‐diketones are introduced as gem‐difluoroenolate precursors for the first example of an organocatalytic asymmetric aldol addition with N‐benzylisatins to form 3‐difluoroalkyl‐3‐hydroxyoxindoles.

  2,2-二氟-1,3-二酮类引入作为宝石-difluoroenolate前体的有机催化不对称醛醇加成与第一示例Ñ -benzylisatins形成3-二氟烷基-3- hydroxyoxindoles。
• Organocatalytic Enantioselective Synthesis of Tetrahydro‐Furanyl Spirooxindoles via [3+2] Annulations of 3‐Hydroxyoxindoles and Cyclic Ketolactams
  作者：Yue Liu、Ying Zhang、Qian‐Wei Huang、Chuan Gou、Qing‐Zhu Li、Qing‐Song Dai、Hai‐Jun Leng、Jun‐Long Li

  DOI：10.1002/adsc.202100033

  日期：2021.4.13

  Asymmetric construction of pharmacologically interesting tetrahydrofuranyl spirooxindole frameworks has been achieved through organocatalytic [3+2] annulations of the readily available 3‐hydroxyoxindoles and pyrrolidone‐derived cyclic ketolactams. A variety of chiral spiro tetrahydrofuranyl products, which contain four contiguous stereocenters including two tetrasubstituted carbon centers, have been

  通过有机催化[3 + 2]环解现成的3-羟基氧吲哚和吡咯烷酮衍生的环状酮内酰胺，可以实现药理学上有趣的四氢呋喃基螺并恶吲哚骨架的不对称构建。快速合成了多种手性螺环四氢呋喃基产品，这些产品包含四个连续的立体中心，其中包括两个四取代的碳中心，收率很高（高达99％，> 95：5 dr和99：1 er）。半酮基部分的合成衍生化使得能够将各种卤素原子以立体有择的方式安装到结构复杂的分子中。初步筛选了抗癌生物活性，并且4 w显示出对一组癌细胞系增殖的明显抑制能力。