7-羟基吲哚-2-羧酸乙酯 | 84638-84-6

• 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
• 中文名称: 7-羟基吲哚-2-羧酸乙酯
• 英文名称: ethyl 7-hydroxyindole-2-carboxylate
• 英文别名: Ethyl 7-hydroxy-1H-indole-2-carboxylate
• CAS: 84638-84-6
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: SUFWHESGARMYGI-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202 °C(Solv: methanol (67-56-1))
• 沸点：
  410.4±25.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：

  7-羟基吲哚-2-羧酸乙酯 在 potassium phosphate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 ethyl 7-phenyl-1H-indole-2-carboxylate
  参考文献：
  名称：

  Design and synthesis of calindol derivatives as potent and selective calcium sensing receptor agonists

  摘要：

  We report the first comprehensive structure-activity study of calindol (4, (R)-N-[(1H-indol-2-yl) methyl]1-(1-naphthyl) ethanamine), a positive allosteric modulator, or calcimimetic, of the calcium sensing receptor (CaSR). While replacement of the naphthyl moiety of calindol by other aromatic groups (phenyl, biphenyl) was largely detrimental to calcimimetic activity, incorporation of substituents on the 4, 5 or 7 position of the indole portion of calindol was found to provide either equipotent derivatives compared to calindol (e.g., 4-phenyl, 4-hydroxy, 5-hydroxycalindol 44, 52, 53) or, in the case of 7-nitrocalindol (51), a 6-fold more active calcimimetic displaying an EC50 of 20 nM. Unlike calindol, the more active CaSR calcimimetics were shown not to act as antagonists of the closely related GPRC6A receptor, suggesting a more selective profile for these new analogues. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.12.019
• 作为产物：
  描述：

  7-溴-1H-吲哚-2-甲酸乙酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 双氧水 、 potassium acetate 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 14.0h， 生成 7-羟基吲哚-2-羧酸乙酯
  参考文献：
  名称：

  WO2020033784A5

  摘要：

  公开号：

  WO2020033784A5

文献信息

• Synthetic Studies on Indoles and Related Compounds. XXXIX. New Strategy for Indole Synthesis from Ethyl Pyrrole-2-carboxylate.
  作者：Masanobu TANI、Takahiro ARIYASU、Masanori OHTSUKA、Terumi KOGA、Yumi OGAWA、Yuusaku YOKOYAMA、Yasuoki MURAKAMI

  DOI：10.1248/cpb.44.55

  日期：——

  As a synthetic application of the previously reported C4-acylation of ethyl pyrrole-2-carboxylate (1), a new strategy for indole synthesis was developed. Ethyl pyrrole-2-carboxylate (1) was allowed to react with succinic anhydride or 3-methoxycarbonylpropionyl chloride to give, in good yield, a C4-succinyl derivative of 1, which was converted into ethyl 7-oxo-4, 5, 6, 7-tetrahydroindole-2-carboxylate (6) as a key intermediate for indole synthesis. Starting from 6, several indoles functionalized on the benzene moiety were synthesized.

  作为之前报道的乙基吡咯-2-羧酸酯（1）C4-酰化反应的综合应用，开发了一种合成吲哚的新策略。乙基吡咯-2-羧酸酯（1）与琥珀酸酐或3-甲氧基羰基丙酰氯反应，以良好产率得到1的C4-琥珀酰衍生物，该衍生物被转化为乙基7-氧代-4,5,6,7-四氢吲哚-2-羧酸酯（6），这是合成吲哚的关键中间体。从6出发，合成了几种在苯环上带有官能团的吲哚化合物。
• Indole derivatives pharmaceutical preparations based thereon, and
  申请人：Schering Aktiengesellschaft

  公开号：US04835175A1

  公开（公告）日：1989-05-30

  Indole derivatives of Formula I ##STR1## wherein R.sub.1 is hydrogen, alkyl of 1-6 carbon atoms, or benzyl R.sub.2 is hydrogen, alkyl of up to 4 carbon atoms, free or esterified hydroxyalkyl of up to 4 carbon atoms, or free, amidated or esterified carboxy or carboxyalkyl, R.sub.3 is hydrogen or alkyl containing 1-6 carbon atoms, R.sub.4 is hydrogen or alkyl containing 1-6 carbon atoms and R.sub.5 is hydrogen, or alkyl, alkenyl, or cycloalkyl, all of which per se contain up to 6 carbon atoms, and all of which are optionally substituted by a free or esterified carboxy group or by an optionally substituted phenyl group; or a polymethylene group of up to 8 carbon atoms linking the first indole residue to a second indole residue of Formula Ia ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are as defined above, and the physiologically acceptable salts thereof with acids and, optionally, their alkali metal and alkaline earth metal salts, possess valuable pharmacological properties, such as stimulating .beta.-receptors and prevention of premature labor, are described.

  Formula I中的吲哚衍生物##STR1##其中R.sub.1是氢，1-6个碳原子的烷基，或苄基R.sub.2是氢，最多4个碳原子的烷基，自由或酯化的最多4个碳原子的羟基烷基，或自由的，酰化的或酯化的羧基或羧基烷基，R.sub.3是氢或含有1-6个碳原子的烷基，R.sub.4是氢或含有1-6个碳原子的烷基，R.sub.5是氢，或烷基，烯基，或环烷基，这些本身包含最多6个碳原子，并且这些都可以选择地被自由或酯化的羧基或通过一个可选择地被取代的苯基团取代；或者是一个最多含有8个碳原子的聚亚甲基基团，将第一个吲哚残基与Formula Ia的第二个吲哚残基连接起来##STR2##其中R.sub.1，R.sub.2，R.sub.3和R.sub.4如上所定义，并且其与酸的生理上可接受的盐，以及可选地其碱金属和碱土金属盐，具有有价值的药理特性，如刺激β-受体和预防早产。
• Fischer indolization of 2-sulfonyloxyphenylhydrazones: A new and practical approach for preparing 7-oxygenated indoles and application to the first synthesis of eudistomidin-A. (Fischer indolization and its related compounds. Part 28)
  作者：Yasuoki Murakami、Toshiko Watanabe、Hiroyuki Takahashi、Hiroshi Yokoo、Yoshie Nakazawa、Michie Koshimizu、Nori Adachi、Masami Kurita、Tomoko Yoshino、Takayuki Inagaki、Maki Ohishi、Mari Watanabe、Masanobu Tani、Yuusaku Yokoyama

  DOI：10.1016/s0040-4020(97)10255-1

  日期：1998.1

  An efficient method for synthesis of 7-oxygenated indoles was established by Fischer indolization of the phenylhydrazones (10) with a sulfonyloxy group at the ortho-position. This method was applied to the first synthesis of the calmodulin antagonist eudistomidin-A (2).

  通过对在邻位具有磺酰氧基的苯hydr（10）进行费歇尔吲哚化，建立了一种有效的7-氧化吲哚合成方法。该方法被应用于钙调蛋白拮抗剂大毒dist素-A（2）的首次合成。
• Albrecht; Heindl; Loge, European Journal of Medicinal Chemistry, 1985, vol. 20, # 1, p. 57 - 60
  作者：Albrecht、Heindl、Loge

  DOI：——

  日期：——
• A Procedure for Transforming Indoles into Indolequinones
  作者：Andrew S. Eastabrook、Christy Wang、Emma K. Davison、Jonathan Sperry

  DOI：10.1021/jo502509s

  日期：2015.1.16

  A procedure that converts a series of structurally diverse, readily available indole derivatives to their corresponding indolequinones is described. The three-step route commences with an iridium catalyzed C-H borylation to give a 7-borylindole that upon oxidationhydrolysis affords the 7-hydroxyindole. Subsequent oxidation provides the indolequinone.