ethyl 2-amino-4,7-dimethoxyindan-2-carboxylate | 141104-67-8

• 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-4,7-dimethoxyindan-2-carboxylate
• 英文别名: Ethyl 2-amino-4,7-dimethoxy-1,3-dihydroindene-2-carboxylate；ethyl 2-amino-4,7-dimethoxy-1,3-dihydroindene-2-carboxylate
• CAS: 141104-67-8
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: BYLRPBPXKKNADJ-UHFFFAOYSA-N

物化性质

• 沸点：
  408.0±45.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-4,7-dimethoxyindan-2-carboxylate 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 生成 Ethyl 2-[[2-[(2-acetamido-2-methylpropanoyl)amino]-2-methylpropanoyl]amino]-4,7-dioxo-1,3-dihydroindene-2-carboxylate
  参考文献：
  名称：

  Synthesis of a New Rigid Quinone-Amino Acid and Diels-Alder Extension to Higher Quinones

  摘要：

  通过一种新颖的方法合成了带有 1,4-苯醌和 1,4-蒽醌侧链的缺电子环状 α-氨基酸衍生物。2-amino-4,7-dimethoxy-indan-2-carboxylic acid（2-氨基-4,7-二甲氧基-茚满-2-羧酸）是一种常见的前体，可在最终的氧化和琥珀化反应之前加入肽中。

  DOI：

  10.1246/cl.1993.299
• 作为产物：
  描述：

  ethyl 4,7-dimethoxy-2-isocyanoindan-2-carboxylate 在 盐酸 作用下， 以 乙醇 为溶剂， 以88%的产率得到ethyl 2-amino-4,7-dimethoxyindan-2-carboxylate
  参考文献：
  名称：

  在相转移催化条件下合成基于茚满的不寻常的α-氨基酸衍生物。

  摘要：

  在固液相转移催化条件下合成了构象受限的环状α-氨基酸衍生物。该方法学涉及将异氰基乙酸乙酯与各种α，α'-二溴邻二甲苯衍生物[α，α'-二溴邻二甲苯5，5，2,3-双（溴甲基）-1，4-二甲氧基苯的双烷基化。 6，1,2-双（溴甲基）-4,5-二溴苯7，2，3-双（溴甲基）萘8，1,8-双（溴甲基）萘9，6,7-双（溴甲基）- 2,2-二甲基-1H-苯并-1,3（2H）-二酮10，2，3-双（溴甲基）-1,4-蒽醌11，6，7，7-双（溴甲基）喹喔啉12，3,4 -双（溴甲基）呋喃13，1,2，4,5-四（溴甲基）苯28，和六（溴甲基）苯30]，以碳酸钾为碱，硫酸四丁铵硫酸盐为相转移催化剂，得到相应的异腈衍生物，将其在乙醇中用HCl水解后得到氨基酯。使用这种方法，制备了电子不足的以及富电子的和卤素取代的基于茚满的α-氨基酸。还描述了双茚满以及三茚满α-氨基酯的制备。

  DOI：

  10.1021/jo991387v

文献信息

• Organic crystal engineering with piperazine-2,5-diones. 1. Crystal packing of piperazinediones derived from substituted 2-aminoindan-2-carboxylic acids
  作者：Lawrence J. Williams、B. Jagadish、Scott R. Lyon、Robin A. Kloster、Michael D. Carducci、Eugene A. Mash

  DOI：10.1016/s0040-4020(99)00925-4

  日期：1999.12

  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.
• 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.
• Organic Crystal Engineering with 1,4-Piperazine-2,5-diones. 6. Studies of the Hydrogen-Bond Association of Cyclo[(2-methylamino-4,7-dimethoxyindan-2-carboxylic acid)(2-amino-4,7-dimethoxyindan-2-carboxylic acid)]
  作者：Robin A. Weatherhead-Kloster、Hugh D. Selby、Walter B. Miller、Eugene A. Mash

  DOI：10.1021/jo0509096

  日期：2005.10.1

  [GRPAHIC]The title 1,4-piperazine-2,5-dione was synthesized in 23% yield over six steps from ethyl 2-amino4,7-dimethoxyindan-2-carboxylate. Crystallization by slow diffusion of ether into a chloroform solution and by slow evaporation of an ethanol-chloroform-benzene solution produced polymorphic crystalline forms as determined by single-crystal X-ray analysis. The polymorphs exhibited different hydrogen-bonding networks. The association of this piperazinedione in solution was studied using mass spectrometric and nuclear magnetic resonance spectroscopic techniques. The MS and NMR data were interpreted using the solid-state structures as models for solution aggregation. Association constants extracted from the NMR data are in line with those of other cyclic cis amides in chloroform solvent.