(R)-methyl 2-(1-benzyl-3-hydroxy-2-oxoindolin-3-yl)acetate | 1380340-91-9

• 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: (R)-methyl 2-(1-benzyl-3-hydroxy-2-oxoindolin-3-yl)acetate
• 英文别名: methyl 2-[(3R)-1-benzyl-3-hydroxy-2-oxoindol-3-yl]acetate
• CAS: 1380340-91-9
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: NKNUGGHUBYLROH-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 (1-苄基-3-羟基-2-氧代-2,3-二氢-1H-吲哚-3-基)-乙酸 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 0.25h， 生成 (R)-methyl 2-(1-benzyl-3-hydroxy-2-oxoindolin-3-yl)acetate 、 (S)-methyl 2-(1-benzyl-3-hydroxy-2-oxoindolin-3-yl)acetate
  参考文献：
  名称：

  Acetylphosphonate as a Surrogate of Acetate or Acetamide in Organocatalyzed Enantioselective Aldol Reactions

  摘要：

  Highly enantioselective aldol reactions of acetylphosphonates and activated carbonyl compounds was realized with cinchona alkaloid derived catalysts, in which the acetylphosphonate was directly used as an enolate precursor for the first time. The aldol product obtained was converted in situ to its corresponding ester or amide through methanolysis or aminolysis. The overall process may be viewed as formal highly enantioselective acetate or acetamide aldol reactions, which are very difficult to achieve directly with organocatalytic methods.

  DOI：

  10.1021/ol301270w

文献信息

• 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。