(indol-3-yl)glycolic acid methyl ester | 78205-41-1

• 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: (indol-3-yl)glycolic acid methyl ester
• 英文别名: methyl indol-3-yl(hydroxy)acetate；methyl 3-indolylglycolate；methyl 2-hydroxy-2-(1H-indol-3-yl)acetate；hydroxy-indol-3-yl-acetic acid methyl ester；Hydroxy-indol-3-yl-essigsaeure-methylester
• CAS: 78205-41-1
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: VXWPKONNOHOWMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (indol-3-yl)glycolic acid methyl ester 在 pH 1 buffer 作用下， 以 甲醇 为溶剂， 生成 methyl 2-indol-3-yl(methoxy)acetate
  参考文献：
  名称：

  Amat-Guerri, Francisco; Martinez-Utrilla, Roberto; Pascual, Conrad, Journal of Chemical Research, Miniprint, 1984, # 5, p. 1578 - 1586

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基吲哚-3-乙酸盐 在 N,N-diethyl-O-mesitylenesulfonylhydroxylamine 作用下， 以40%的产率得到(indol-3-yl)glycolic acid methyl ester
  参考文献：
  名称：

  FeCl 3和仲胺诱导的3-吲哚-3-乙酸甲酯的氧化

  摘要：

  在二甲胺存在下，用FeCl 3氧化吲哚-3-乙酸甲酯，得到α-（二甲基氨基）-吲哚-3-乙酸甲酯，4d可以被季铵化，随后在乙酸存在下与吲哚-3-乙酸甲酯偶联。 LDA。

  DOI：

  10.1016/s0040-4039(01)93780-3

文献信息

• Tyrosine phosphatase inhibitors
  申请人：——

  公开号：US20030144338A1

  公开（公告）日：2003-07-31

  A compound of the formula (I): 1 wherein X 1 and X 2 are the same or different and each is a bond or a spacer having 1 to 20 atom(s) in the main chain; one of R 1 and R 2 is a cycle group having substituent(s) selected from 1) an optionally substituted carboxy-C 1-6 alkoxy group and 2) an optionally substituted carboxy-C 1-6 aliphatic hydrocarbon group, wherein the cycle group optionally has additional substituent(s), and the other is an optionally substituted cycle group or a hydrogen atom; and R 3 , R 4 and R 5 are the same or different and each is a hydrogen atom or a substituent, or R 4 may link together with R 3 or R 5 to form an optionally substituted ring; provided that when R 3 is a hydrogen atom, R 4 is a hydrogen atom and R 5 is methyl, X 2 —R 2 is not 4-cyclohexylphenyl; when R 3 is 4-methoxyphenyl, R 4 is a hydrogen atom and R 5 is methyl, X 2 —R 2 is not 4-methoxyphenyl; and when R 1 or R 2 is a hydrogen atom, the adjacent X 1 or X 2 is not a C 1-7 alkylene; or a salt thereof exhibits a protein tyrosine phosphatase inhibitory action and is useful as a prophylactic or therapeutic agent for diabetes or the like.

  式（I）的化合物： 其中X1和X2相同或不同，每个都是主链中具有1至20个原子的键或间隔物； R1和R2中的一个是具有取代基的环基，所述取代基选自1）可选择地取代的羧基-C1-6烷氧基和2）可选择地取代的羧基-C1-6脂肪烃基，其中所述环基可选择地具有额外的取代基，另一个是可选择地取代的环基或氢原子；以及 R3、R4和R5相同或不同，每个是氢原子或取代基，或R4可以与R3或R5结合形成可选择地取代的环； 但是当R3是氢原子时，R4是氢原子且R5是甲基时，X2—R2不是4-环己基苯基；当R3是4-甲氧基苯基，R4是氢原子且R5是甲基时，X2—R2不是4-甲氧基苯基；当R1或R2是氢原子时，相邻的X1或X2不是C1-7烷基； 或其盐具有蛋白酪氨酸磷酸酶抑制作用，并且可用作糖尿病等疾病的预防或治疗剂。
• Directed C3-Alkoxymethylation of Indole via Three-Component Cascade Reaction
  作者：Chao Pi、Xiaohang Yin、Xiuling Cui、Yuwen Ma、Yangjie Wu

  DOI：10.1021/acs.orglett.9b00357

  日期：2019.4.5

  An efficient and regioselective C3-alkoxymethylation of indoles has been developed with aldehydes and alcohols via three-component cascade reaction under transition-metal free conditions. This method allows for rapid access to a variety of C3-alkoxymethylaed free (N–H) indole in up to 98% yield with excellent regioselectivity. The titled products are useful building blocks in organic synthesis.

  通过在无过渡金属条件下的三组分级联反应，利用醛和醇开发了吲哚的高效且区域选择性的C3-烷氧基甲基化反应。这种方法可以快速获得各种C3-烷氧基甲基化的游离（NH）吲哚，具有高达98％的产率，并具有出色的区域选择性。标题产品是有机合成中有用的组成部分。
• THE FORMATION OF 1- AND 3-SUBSTITUTED INDOLES IN THE REACTION BETWEEN INDOLE AND SODIUM GLYOXYLATE
  作者：Francisco Amat-Guerri、Roberto Martinez-Utrilla、Conrad Pascual

  DOI：10.1246/cl.1981.511

  日期：1981.4.5

  The reaction between indole and sodium glyoxylate under basic conditions produces, in addition to the expected sodium 3-indolylglycolate (3a), the 1-substituted derivative (4a). 3a partially condenses with unreacted indole and with 4a yielding the corresponding 3 ,3′-diindolyllmethane derivatives, 5a and 6a. All compounds were isolated and identified as methyl esters.

  除了预期的 3-吲哚基乙醇酸钠 (3a) 外，吲哚和乙醛酸钠在碱性条件下的反应还生成 1-取代衍生物 (4a)。3a 与未反应的吲哚和 4a 部分缩合，产生相应的 3,3'-二吲哚基甲烷衍生物 5a 和 6a。所有化合物均被分离并鉴定为甲酯。
• TYROSINE PHOSPHATASE INHIBITORS
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1284260A1

  公开（公告）日：2003-02-19

  A compound of the formula (I):    wherein X1 and X2 are the same or different and each is a bond or a spacer having 1 to 20 atom(s) in the main chain;    one of R1 and R2 is a cycle group having substituent(s) selected from 1) an optionally substituted carboxy-C1-6 alkoxy group and 2) an optionally substituted carboxy-C1-6 aliphatic hydrocarbon group, wherein the cycle group optionally has additional substituent(s), and the other is an optionally substituted cycle group or a hydrogen atom; and    R3, R4 and R5 are the same or different and each is a hydrogen atom or a substituent, or R4 may link together with R3 or R5 to form an optionally substituted ring;    provided that when R3 is a hydrogen atom, R4 is a hydrogen atom and R5 is methyl, X2-R2 is not 4-cyclohexylphenyl; when R3 is 4-methoxyphenyl, R4 is a hydrogen atom and R5 is methyl, X2-R2 is not 4-methoxyphenyl; and when R1 or R2 is a hydrogen atom, the adjacent X1 or X2 is not a C1-7 alkylene; or a salt thereof exhibits a protein tyrosine phosphatase inhibitory action and is useful as a prophylactic or therapeutic agent for diabetes or the like.

  式(I)化合物： 其中 X1 和 X2 相同或不同，且各自为键或在主链中具有 1 至 20 个原子的间隔物； R1 和 R2 中的一个是具有选自 1）任选取代的羧基-C1-6 烷氧基和 2）任选取代的羧基-C1-6 脂肪族烃基的取代基的循环基团，其中循环基团任选具有附加取代基，另一个是任选取代的循环基团或氢原子；以及 R3、R4 和 R5 相同或不同，且各自为氢原子或取代基，或 R4 可与 R3 或 R5 连接形成任选取代的环； 条件是当 R3 是氢原子、R4 是氢原子且 R5 是甲基时，X2-R2 不是 4-环己基苯基；当 R3 是 4-甲氧基苯基、R4 是氢原子且 R5 是甲基时，X2-R2 不是 4-甲氧基苯基；以及当 R1 或 R2 是氢原子时，相邻的 X1 或 X2 不是 C1-7 亚烷基； 或其盐具有蛋白酪氨酸磷酸酶抑制作用，可用作糖尿病或类似疾病的预防或治疗剂。
• The formation of 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)cyclopent-2-enone derivatives from ascorbigens
  作者：Alexander M Korolev、Larisa N Yudina、Ilyia I Rozhkov、Ludmila N Lysenkova、Eduard I Lazhko、Yury N Luzikov、Maria N Preobrazhenskaya

  DOI：10.1016/s0008-6215(00)00310-4

  日期：2001.2

  A facile preparation is described of 3-(indol-3-yl)-2-hydroxy-4-hydroxymethylcyclopent-2-enone and its N-derivatives in 15-40% yields by the degradation of ascorbigen or its N-derivatives in a warm solution of L-ascorbic acid through a sequential domino reaction. The same cyclopentenone derivatives were obtained in 30-40% yields by the condensation of (N-alkylindol-3-yl)glycolic acids with ascorbic acid. 2,6-Dihydroxy-1-(indol-3-yl)hexa-1,4-diene-3-one and 2-hydroxy-4-hydroxymethyl-5-(indol-3-yl)cyclopent-2-enone were identified as intermediates in this reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.