3-hydroxy-1-phenylindolin-2-one | 93717-59-0

• 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: 3-hydroxy-1-phenylindolin-2-one
• 英文别名: N-Phenyl-dioxindol；3-Hydroxy-1-phenyl-indolin-2-on；N-phenyl-3-hydroxy-oxindole；3-hydroxy-1-phenyl-3H-indol-2-one
• CAS: 93717-59-0
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: RRUNSHTZNYVWNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 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：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-1-phenylindolin-2-one 、 3-(1H-pyrazole-1-carbonyl)-2H-chromen-2-one 在 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Coumarin-3-Formylpyrazoles 作为 3-Carbon Partners 与 3-Hydroxyoxindoles 通过酯化/Michael 加成序列的不对称形式 (3 + 2) 环缩合

  摘要：

  第一个涉及 α,β-不饱和吡唑酰胺作为 3-碳伙伴的对映选择性形式 (3 + 2) 环缩合反应是逐步完成的。逐步酯化/迈克尔加成顺序分别由 Zn(OTf) 2和奎宁-squaramide 衍生物促进。该协议能够从香豆素-3-甲酰基吡唑和 3-羟基氧吲哚中获得螺稠合五环螺氧吲哚，总收率良好至令人满意（高达 91%），具有出色的 dr（所有情况 >20:1 dr）和高 ee 值（高达到 99%）。机理研究有助于阐明该过程的对映选择性事件。

  DOI：

  10.1021/acs.joc.2c01757
• 作为产物：
  描述：

  1-苯基靛红 在 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 3-hydroxy-1-phenylindolin-2-one
  参考文献：
  名称：

  一锅法合成C2-季2-羟基吲哚酚的多米诺·格利雅（Domino Grignard）加成和氧化反应。

  摘要：

  我们在本文中描述了3-羟基氧吲哚对格氏试剂的未探索的反应性，从而能够以高收率快速获得广泛的非天然C2-季2-羟基吲哚酚。该反应通过机械上引人入胜的一锅1，2-氢化物转移，然后通过自氧化途径进行。通过合成一类新的双吲哚螺螺呋喃衍生物证明了该方法的实用性。

  DOI：

  10.1021/acs.orglett.9b03022

文献信息

• Coumarin-3-formylpyrazoles as 3-carbon synthons in cyclocondensation for the synthesis of spiro-fused pentacyclic spirooxindoles
  作者：Chuan-Wen Lei、Chuan-Bao Zhang、Zhen-Hua Wang、Ke-Xin Xie、Jian-Qiang Zhao、Ming-Qiang Zhou、Xiao-Mei Zhang、Xiao-Ying Xu、Wei-Cheng Yuan

  DOI：10.1039/c9ob02434d

  日期：——

  Coumarin-3-formylpyrazoles have been synthesized and applied as 3-carbon synthons in reaction with 3-hydroxyoxindoles by using DABCO as the catalyst. A range of structurally diverse spiro-fused pentacyclic spirooxindoles, bearing a spirooxindole-γ-lactone and a 3,4-dihydrocoumarin substructure, could be smoothly obtained in good to excellent yields (up to 99%) with excellent diastereoselectivities

  合成了香豆素-3-甲酰基吡唑，并以DABCO为催化剂，将其作为3-碳合成子与3-羟基羟吲哚反应。可以平稳地获得一系列结构多样的螺旋稠合的五环螺旋螺环，它们带有螺氧吲哚-γ-内酯和3,4-二氢香豆素亚结构，具有良好的至优异的产率（高达99％）和非对映选择性（所有情况> 20） ：1个博士）。通过使用手性有机催化剂初步研究了该串联反应的不对称形式。
• Organocatalytic Asymmetric Michael/Cyclization Cascade Reactions of 3-Hydroxyoxindoles/3-Aminooxindoles with α,β-Unsaturated Acyl Phosphonates for the Construction of Spirocyclic Oxindole-γ-lactones/lactams
  作者：Lin Chen、Zhi-Jun Wu、Ming-Liang Zhang、Deng-Feng Yue、Xiao-Mei Zhang、Xiao-Ying Xu、Wei-Cheng Yuan

  DOI：10.1021/acs.joc.5b02253

  日期：2015.12.18

  Enantioselective Michael/cyclization cascade reactions of 3-hydroxyoxindoles/3-aminooxindoles with α,β-unsaturated acyl phosphonates by using a cinchonine derived squaramide as the catalyst were developed. A broad range of spirocyclic oxindole-γ-lactones/lactams could be obtained in moderate to excellent yields (up to 98%) with good to excellent diastereo- and enantioselectivities (up to >99:1 dr and

  以辛可宁衍生的方酰胺为催化剂，开发了3-羟基氧吲哚/ 3-氨基氧吲哚与α，β-不饱和酰基膦酸酯的对映选择性迈克尔/环化级联反应。在温和条件下，可以以中等至优异的收率（高达98％）获得良好的非对映和对映选择性（高达> 99：1 dr和97％ee）的各种螺环羟吲哚-γ-内酯/内酰胺类化合物。 。这项工作代表了有关α，β-不饱和酰基膦酸酯用于螺环羟吲哚的不对称结构的第一个例子。
• An intermolecular C–H functionalization method for the synthesis of 3-hydroxy-2-oxindoles
  作者：Jinsen Chen、Chao Song、Pei Chen、Jin Zhu

  DOI：10.1039/c4ob01643b

  日期：——

  An intermolecular C–H functionalization with a denitrosation-triggered cyclization method is developed for the synthesis of 3-hydroxy-2-oxindoles.

  一种利用去亚硝基化引发环化反应的分子间C-H官能化方法被开发用于合成3-羟基-2-氧化吲哚。
• Asymmetric hydrogenation of α-keto acid derivatives by rhodium-}amidophosphine-phosphinite{ catalysts
  作者：Jean-François Carpentier、André Mortreux

  DOI：10.1016/s0957-4166(97)00078-5

  日期：1997.4

  The enantioselective hydrogenation of several alpha-keto esters (3a-f, 5a-j), alpha-keto amides (7a-e) and isatine derivatives (9a-d) with a set of four representative neutral homogeneous rhodium-amidophosphine-phosphinite catalysts has been investigated. Trifluoroacetato-Rh-AMPP catalytic precursors promoted the rapid, efficient synthesis of aliphatic oc-hydroxy esters 4a-f in moderate to high enantioselectivities (66-95% ee), in contrast to most aromatic alpha-hydroxy esters 6a-j (8-81% ee). Best enantioselectivities for alpha-hydroxy amides 8a-e (85-95% ee) and dioxindoles 10a-d (80-94% ee) were obtained with chloro-Rh-AMPP precursors. It is proposed that, contrary to alpha-keto amides, alpha-keto esters do not chelate onto the rhodium center and that, in such circumstances, the asymmetric induction is mainly controlled by the steric hindrance around the C=O function. (C) 1997 Elsevier Science Ltd.
• Organocatalytic, Enantioselective, Polarity-Matched Ring-Reorganization Domino Sequence Based on the 3-Oxindole Scaffold
  作者：Ji-Wei Ren、Lan Zheng、Zhi-Peng Ye、Zhi-Xiong Deng、Zhen-Zhen Xie、Jun-An Xiao、Fa-Wei Zhu、Hao-Yue Xiang、Xiao-Qing Chen、Hua Yang

  DOI：10.1021/acs.orglett.9b00477

  日期：2019.4.5

  A one-pot squaramide-catalyzed enantioselective ring-reorganization domino sequence (Michael addition/intramolecular ring-opening/lactamization) of 3-hydroxyoxindole and methyleneindolinone, which can be readily derived from 3-oxindole, has been established in this work. As a result, novel polycyclic quinolinone-spirooxindoles bearing three contiguous chiral centers were efficiently and step-economically assembled under mild conditions in high yields (up to 97%) with excellent enantioselectivities (up to >99% ee) and moderate to good diastereoselectivities (up to >95:5 dr).