6-bromo-3-hydroxy-1-methylindolin-2-one | 1458733-95-3

• 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: 6-bromo-3-hydroxy-1-methylindolin-2-one
• CAS: 1458733-95-3
• 化学式: C₉H₈BrNO₂
• 分子量: 242.072
• InChiKey: ARYPYFNBIONWEV-UHFFFAOYSA-N

物化性质

• 沸点：
  454.0±45.0 °C(predicted)
• 密度：
  1.738±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-羟基查耳酮 、 6-bromo-3-hydroxy-1-methylindolin-2-one 在 三氟甲磺酸 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以75%的产率得到6-bromo-1-methyl-2'-phenyl-5'H-spiro[indoline-3,4'-[2,5]methanobenzo[d][1,3]dioxepin]-2-one
  参考文献：
  名称：

  Metal-free diastereoselective construction of bridged ketal spirooxindoles via a Michael addition-inspired sequence

  摘要：

  通过TfOH催化的高对映选择性Michael加成/缩醛化序列，将3-羟基吲哚和邻位-羟基查尔酮进行反应，产生生物重要的桥接缩醛螺环吲哚，收率在中等到优良之间。

  DOI：

  10.1039/c7cc05813f
• 作为产物：
  描述：

  ethyl 2-(4-bromo-2-(methyl(nitroso)amino)phenyl)-2-hydroxyacetate 在 盐酸 、 氨基磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 以81%的产率得到6-bromo-3-hydroxy-1-methylindolin-2-one
  参考文献：
  名称：

  An intermolecular C–H functionalization method for the synthesis of 3-hydroxy-2-oxindoles

  摘要：

  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。

  DOI：

  10.1039/c4ob01643b

文献信息

• An unexpected cascade reaction of 3-hydroxyoxindoles with coumarin-3-carboxylates to construct 2,3-dihydrobenzofuran spirooxindoles
  作者：Kuan Zhang、Huabin Han、Lele Wang、Ziying Zhang、Qilin Wang、Wenjing Zhang、Zhanwei Bu

  DOI：10.1039/c9cc07114h

  日期：——

  An unexpected Michael addition-inspired ring-opening/closure cascade reaction of 3-hydroxyoxindoles with coumarin-3-carboxylates was developed to access new dihydrobenzofuran or dihydrobenzothiophene spirooxindoles in 68–98% yields. This reaction not only provides an expedient and convenient method to assemble dihydrobenzofuran spirooxindoles, but also establishes a new reaction mode of coumarin-3-carboxylates

  开发了一个出乎意料的迈克尔加成反应的3-羟基羟吲哚与香豆素3-羧酸酯的开环/闭合级联反应，以68-98％的产率获得新的二氢苯并呋喃或二氢苯并噻吩螺环辛多。该反应不仅为组装二氢苯并呋喃spirooxindoles提供了一种方便快捷的方法，而且建立了香豆素-3-羧酸酯的新反应方式。此外，它代表具有C 1合成子的3-羟基羟吲哚的第一个实例，其具有以羟基为离去基团的亲核和亲电双重特性。重要的是，这种方法为XEN907类似物提供了一种快速而强大的方法。
• Oxidative NHC catalysis: direct activation of β sp³ carbons of saturated acid chlorides
  作者：Shi-Ya Zhu、Hua Zhang、Qing-Wei Ma、Dou Liu、Xin-Ping Hui

  DOI：10.1039/c8cc08578a

  日期：——

  activation of saturated acid chlorides by oxidative N-heterocyclic carbene catalysis has been successfully utilized to synthesize enantio-enriched spirooxindole lactones and δ-lactones. The reaction involves the transformation of the β sp3 carbon of saturated acid chlorides into an electrophilic carbon as a key step. The product was obtained in excellent yield and stereoselectivity.

  已成功利用氧化N-杂环卡宾催化对饱和酰氯的首次活化，来合成对映体富集的螺并吲哚内酯和δ-内酯。该反应涉及将饱和酰氯的βsp 3碳转化为亲电子碳的关键步骤。以优异的产率和立体选择性获得产物。
• An organocatalytic asymmetric sequential allylic alkylation–cyclization of Morita–Baylis–Hillman carbonates and 3-hydroxyoxindoles
  作者：Qi-Lin Wang、Lin Peng、Fei-Ying Wang、Ming-Liang Zhang、Li-Na Jia、Fang Tian、Xiao-Ying Xu、Li-Xin Wang

  DOI：10.1039/c3cc45139a

  日期：——

  The first organocatalytic asymmetric sequential allylic alkylation–cyclization of Morita–Baylis–Hillman carbonates and 3-hydroxyoxindoles has been developed to afford spirooxindoles bearing α-methylene-γ-butyrolactone motifs in 25–85% yield, 60–94% ee and up to >20 : 1 diastereoselectivity.

  第一个有机催化不对称连续烯丙基烷基化-环化 Morita-Baylis-Hillman 碳酸酯和 3-羟基吲哚已被开发出来，可提供带有 α-亚甲基-γ-丁内酯基序的螺吲哚，产率 25-85%，产率 60-60 94% ee 和高达 >20-:-1 非对映选择性。
• 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).