methyl 2-(1-benzyl-3-hydroxy-2-oxoindolin-3-yl)acetate | 500220-02-0

• 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: methyl 2-(1-benzyl-3-hydroxy-2-oxoindolin-3-yl)acetate
• 英文别名: Methyl 2-(1-benzyl-3-hydroxy-2-oxoindol-3-yl)acetate
• CAS: 500220-02-0
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: NKNUGGHUBYLROH-UHFFFAOYSA-N

物化性质

• 熔点：
  137-139 °C
• 沸点：
  554.2±50.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  methyl 2-(1-benzyl-3-hydroxy-2-oxoindolin-3-yl)acetate 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到1-benzyl tryptophol
  参考文献：
  名称：

  A versatile synthetic methodology for the synthesis of tryptophols

  摘要：

  Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01048-7
• 作为产物：
  描述：

  1-苯甲酰基-1H-吲哚-2,3-二酮 在 吡啶 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 生成 methyl 2-(1-benzyl-3-hydroxy-2-oxoindolin-3-yl)acetate
  参考文献：
  名称：

  A versatile synthetic methodology for the synthesis of tryptophols

  摘要：

  Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01048-7

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。
• Copper-Catalyzed Selective Electron Transfer Enables Switchable Divergent Synthesis of 3-Functionalized Oxindoles
  作者：Shu-Yun Jiang、Jun Shi、Wei Wang、Yan-Zheng Sun、Wei Wu、Jun-Rong Song、Xiaoyan Yang、Ge-Fei Hao、Wei-Dong Pan、Hai Ren

  DOI：10.1021/acscatal.2c05881

  日期：2023.3.3

  this time-consuming and complex task produces a single type of product via two-electron oxidation using stoichiometric chemical oxidants. Herein, we report a unified and efficient copper-catalyzed selective single-electron transfer strategy for three oxidation reactions of 3-substituted indoles using air (O2) as the terminal oxidant, providing a streamlined and practical synthetic approach to access 3-hydroxyl-

  3-取代吲哚的氧化重排是合成 2-羟吲哚支架的基本有机转化。然而，这项耗时且复杂的任务使用化学计量化学氧化剂通过双电子氧化产生单一类型的产品。在此，我们报告了一种统一且高效的铜催化选择性单电子转移策略，用于使用空气 (O 2 ) 作为末端氧化剂的 3-取代吲哚的三种氧化反应，提供了一种简化且实用的合成方法来获得 3-羟基- , 3-烷氧基-, 和 3-hygrogenous-2-oxindoles通过3-自由基-2-羟基二氢吲哚中间体。这种铜催化方案在生物 3-功能化羟吲哚衍生物的模块化合成中表现出高化学选择性、良好的官能团耐受性和广泛的应用潜力。
• Regioselective synthesis of enantiopure 1,2- and 1,3-dispirooxindoles along with a DFT study
  作者：Kamal Asmari Bardazard、Naeimeh Shahrestani、Amirhosein Zamani、Mehdi Eskandari、Khosrow Jadidi、Mahshid Hamzehloueian、Behrouz Notash

  DOI：10.1039/d2ob02311c

  日期：——

  the enantiomeric purity of the desired products. The mechanism and differences in the regioselectivity of the 1,3-dipolar cycloaddition reactions between the stable azomethane ylides obtained from ninhydrin, pipecolinic acid, and proline with (E)-2-oxoindolin-3-ylideneacetyl sultam were theoretically studied through DFT calculations at the M06-2X/6-31G(d,p) level in methanol.

  在本研究中，使用不同的氨基酸（哌啶酸、肌氨酸、脯氨酸和羟脯氨酸）合成了具有三个或四个连续和两个季立体异构中心的重要对映纯二螺吲哚 [吲哚里西啶、吡咯里西啶和吡咯烷] 衍生物库（高达 96%）通过区域选择性和非对映选择性（高达 99:1）多组分 1,3-偶极环加成策略。根据结果​​，氨基酸的改变导致区域选择性的变化和不寻常的区域异构体（吡咯里西啶与indolizidine/pyrrolidine) 被用来构建一个新的对映体纯的 1,3-dispirooxindole 骨架。环加成的立体化学结果通过单晶 X 射线衍射分析确定，对映体自歧化 (SDE) 测试证实了所需产品的对映体纯度。通过 DFT 计算从理论上研究了从茚三酮、哌啶酸和脯氨酸获得的稳定偶氮甲烷叶立德与 ( E )-2-氧代吲哚啉-3-亚基乙酰基磺胺的1,3-偶极环加成反应的机理和区域选择性差异甲醇中的 M06-2X/6-31G(d
• A versatile synthetic methodology for the synthesis of tryptophols
  作者：Simon J Garden、Rosângela B da Silva、Angelo C Pinto

  DOI：10.1016/s0040-4020(02)01048-7

  日期：2002.10

  Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol. (C) 2002 Elsevier Science Ltd. All rights reserved.