ethyl 2-amino-5,6-dimethylindan-2-carboxylate | 141104-66-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-amino-5,6-dimethylindan-2-carboxylate
• 英文别名: 2-amino-5,6-dimethyl-indan-2-carboxylic acid ethyl ester；ethyl 2-amino-5,6-dimethyl-1,3-dihydroindene-2-carboxylate
• CAS: 141104-66-7
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: OUCSEXWUXBOBNP-UHFFFAOYSA-N

物化性质

• 沸点：
  336.5±42.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-5,6-dimethylindan-2-carboxylate 在 sodium hydroxide 、 碳酸氢钠 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 sodium chloride 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 N-[5,6-dimethyl-2-(carboethoxy)indan-2-yl]-2-[(N-carbo-2,2-dimethylethoxy)amino]indan-2-carboxamide
  参考文献：
  名称：

  Organic crystal engineering with piperazine-2,5-diones. 1. Crystal packing of piperazinediones derived from substituted 2-aminoindan-2-carboxylic acids

  摘要：

  We have postulated that molecules engineered to participate in three chemically distinct and linearly independent intermolecular interactions will self-assemble in a predictable fashion. Six prototypes for molecules capable of manifesting such interactions were synthesized from 2-amino-indan-2-carboxylic acid, 2-amino-5,6-dimethylindan-2-carboxylic acid, and 2-amino-4,7-dimethoxyindan-2-carboxylic acid. These piperazinediones were characterized in solution by NMR spectroscopy and in the solid state by X-ray crystallography. "Ladder-like" intermolecular amide-to-amide hydrogen bonding interactions were observed in each case, establishing tape structures parallel to one crystallographic axis. Tape morphology varied depending on the arene substitution pattern and was governed by the development of arene and/or van der Waals contact interactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00925-4
• 作为产物：
  描述：

  1,2-二(氯甲基)-4,5-二甲苯 在 盐酸 、 sodium hexamethyldisilazane 作用下， 以 乙醚 为溶剂， 反应 2.75h， 生成 ethyl 2-amino-5,6-dimethylindan-2-carboxylate
  参考文献：
  名称：

  A Simple Method for the Synthesis of Cyclic α- Amino Acids

  摘要：

  The benzylidene derivative of glycine ethyl ester was alkylated with various electrophiles to synthesize cyclic alpha-amino acids bearing aromatic and aliphatic side chains.

  DOI：

  10.1016/s0040-4039(00)91675-7

文献信息

• SUBSTITUTED BENZOYLAMINO-INDAN-2-CARBOXYLIC ACIDS AND RELATED COMPOUNDS
  申请人：CAULFIELD Thomas J.

  公开号：US20100113462A1

  公开（公告）日：2010-05-06

  The present invention relates to novel compounds of the formula I: wherein in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, wherein the substituents are as described herein. The inventive compounds have CXCR5 inhibitory activity are particularly useful in treating or preventing various inflammatory diseases, such as rheumatoid arthritis, multiple sclerosis, lupus, Crohn's Disease, associated with the modulation of the human CXCR5 receptor.

  本发明涉及公式I的新化合物：其中在其任何立体异构形式或立体异构形式的混合物中以任何比例，或其生理上可接受的盐，其中取代基如此描述。这些创新化合物具有CXCR5抑制活性，特别适用于治疗或预防各种炎症性疾病，例如类风湿性关节炎，多发性硬化症，红斑狼疮，克罗恩病，与人类CXCR5受体调节相关。
• Substituted benzoylamino-indan-2-carboxylic acids and related compounds
  申请人：Caulfield Thomas Joseph

  公开号：US08569535B2

  公开（公告）日：2013-10-29

  The present invention relates to novel compounds of the formula Ia: in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, wherein the substituents are as described herein. The inventive compounds have CXCR5 inhibitory activity, and are particularly useful in treating or preventing various inflammatory diseases, such as rheumatoid arthritis, multiple sclerosis, lupus, Crohn's Disease, associated with the modulation of the human CXCR5 receptor.

  本发明涉及公式Ia的新化合物：以其立体异构体形式或任何比例的立体异构体混合物或其生理上可接受的盐，其中取代基如本文所述。这些创新化合物具有CXCR5抑制活性，并且在治疗或预防各种炎症性疾病方面特别有用，例如类风湿性关节炎，多发性硬化症，狼疮，克隆氏病，与人类CXCR5受体调节有关。
• WO2008/151211
  申请人：——

  公开号：——

  公开（公告）日：——
• A Simple Method for the Synthesis of Cyclic α- Amino Acids
  作者：Sambasivarao Kotha、Atsuo Kuki

  DOI：10.1016/s0040-4039(00)91675-7

  日期：1992.3

  The benzylidene derivative of glycine ethyl ester was alkylated with various electrophiles to synthesize cyclic alpha-amino acids bearing aromatic and aliphatic side chains.
• US8569535B2
  申请人：——

  公开号：US8569535B2

  公开（公告）日：2013-10-29