酸柑子166 | 72228-39-8

• 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: 酸柑子166
• 英文名称: 2-(1-methylindol-3-yl)propionic acid
• 英文别名: 2-(N-Methyl-3-indolyl)propionic Acid；2-(1-Methyl-indolyl-3)-propionsaeure；α-(1-Methyl-3-indolyl)-propionsaeure；2-(1-methyl-1H-indol-3-yl)propanoic acid；2-(1-methylindol-3-yl)propanoic acid
• CAS: 72228-39-8
• 化学式: C₁₂H₁₃NO₂
• mdl: MFCD09751724
• 分子量: 203.241
• InChiKey: BWJKELIYCFNOEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  酸柑子166 在 水 、 sodium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 5.0h， 生成 2-methyl-2-(1-methyl-1H-indol-3-yl)butanoic acid
  参考文献：
  名称：

  2-Cyano-2-indolylpropanoic acid as a chiral derivatizing agent for the absolute configuration assignment of secondary alcohols and primary amines by 1 H NMR and VCD

  摘要：

  A convenient approach for the absolute configuration assignment of secondary alcohols in the (8R,1'R,2'S,5'R)-15,25, (8S,1'R,2'S,5'R)-15,25, (8R,1'R)-21-24, and (8S,l'R)-21-24 ester series, and of primary amines in the (8R,1'R)-32-37 and (8S,1'R)-32-37 amide series, by means of H-1 NMR and VCD spectroscopy, using 2-cyano-2-indolylpropanoic acid as a chiral derivatizing agent is presented. DFT calculations were carried out to demonstrate the anisotropic effect of the indole skeleton on the chiral alcohol or the amine fragment. Vibrational circular dichroism (VCD) measurements of the above series indicated a VCD bisignated couplet resulting from the interaction of the ester carbonyl group and the -CN group. The absolute configuration assignments were further tested by X-ray diffraction analysis. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.04.011
• 作为产物：
  描述：

  1-甲基-3-吲哚乙酸 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 酸柑子166
  参考文献：
  名称：

  .alpha.-Lithio-3-indolylacetate synthons: generation and synthetic utilization

  摘要：

  DOI：

  10.1021/jo01291a014

文献信息

• Substituted Heteroaromatic Carboxamide and Urea Compounds as Vanilloid Receptor Ligands
  申请人：Frank Robert

  公开号：US20120115903A1

  公开（公告）日：2012-05-10

  Substituted heteroaromatic carboxamide and urea compounds corresponding to formula (i) processes for the preparation thereof, pharmaceutical compositions containing these compounds and also a method of using these compounds in pharmaceutical compositions for treating or inhibiting pain and other conditions mediated at least in part via the vanilloid receptor 1.

  将与式（i）对应的取代杂芳基羧酰胺和脲化合物翻译成中文，以及其制备方法、含有这些化合物的药物组合物，以及在药物组合物中使用这些化合物治疗或抑制至少部分通过辣椒素受体1介导的疼痛和其他症状的方法。
• [EN] SUBSTITUTED HETEROAROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS<br/>[FR] CARBOXAMIDE HÉTÉROAROMATIQUE SUBSTITUÉ ET DÉRIVÉS DE L'URÉE EN TANT QUE LIGANDS DU RÉCEPTEUR VANILLOÏDE
  申请人：GRUENENTHAL GMBH

  公开号：WO2012062462A1

  公开（公告）日：2012-05-18

  The invention relates to substituted heteroaromatic carboxamide and urea derivatives of formula (I), to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions.

  这项发明涉及公式（I）的取代杂环羧酰胺和脲衍生物，涉及其制备方法，含有这些化合物的药物组合物，以及利用这些化合物制备药物组合物。
• Chemospecific Cyclizations of α‐Carbonyl Sulfoxonium Ylides on Aryls and Heteroaryls
  作者：Daniel Clare、Benjamin C. Dobson、Phillip A. Inglesby、Christophe Aïssa

  DOI：10.1002/anie.201910821

  日期：2019.11.4

  The functionalization of aryl and heteroaryls using α‐carbonyl sulfoxonium ylides without the help of a directing group has remained so far a neglected area, despite the advantageous safety profile of sulfoxonium ylides. Described herein are the cyclizations of α‐carbonyl sulfoxonium ylides onto benzenes, benzofurans and N‐p‐toluenesulfonyl indoles in the presence of a base in HFIP, whereas pyrroles

  尽管亚砜叶立德具有有利的安全性，但在没有导向基团帮助的情况下使用α-羰基亚砜叶立德对芳基和杂芳基进行官能化迄今为止仍然是一个被忽视的领域。本文描述了在 HFIP 中碱存在下，α-羰基亚锍叶立德在苯、苯并呋喃和 N-对甲苯磺酰吲哚上的环化，而吡咯和N-甲基吲哚在铱催化剂存在下进行环化。值得注意的是，这两组条件对于每组底物都是化学特异性的。
• Highly Enantioselective Direct Alkylation of Arylacetic Acids with Chiral Lithium Amides as Traceless Auxiliaries
  作者：Craig E. Stivala、Armen Zakarian

  DOI：10.1021/ja205107x

  日期：2011.8.10

  A direct, highly enantioselective alkylation of arylacetic acids via enediolates using a readily available chiral lithium amide as a stereodirecting reagent has been developed. This approach circumvents the traditional attachment and removal of chiral auxiliaries used currently for this type of transformation. The protocol is operationally simple, and the chiral reagent is readily recoverable.

  已经开发出使用容易获得的手性氨基锂作为立体定向试剂通过烯二醇对芳基乙酸进行直接、高度对映选择性的烷基化。这种方法绕过了目前用于此类转化的手性助剂的传统附着和去除。该方案操作简单，手性试剂易于回收。
• HETEROCYCLIC AZA COMPOUNDS
  申请人：Grünenthal GmbH

  公开号：EP3130589A1

  公开（公告）日：2017-02-15

  The invention relates to heterocyclic aza compounds as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

  本发明涉及杂环氮化物作为vanilloid受体配体，含有这些化合物的制药组合物，以及这些化合物用于治疗和/或预防疼痛和其他疾病和/或障碍的用途。