ethyl 2-amino-1-oxoindanecarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: ethyl 2-amino-1-oxoindanecarboxylate
• 英文别名: 2-Amino-1-oxo-indane-2-carboxylic acid ethyl ester；ethyl 2-amino-3-oxo-1H-indene-2-carboxylate
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: QEPSLCKWTXDIHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-1-oxoindanecarboxylate 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 以67 %的产率得到ethyl 1-oxo-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate
  参考文献：
  名称：

  α-氨基-β-氧代酯向 δ-丁内酰胺的环转化

  摘要：

  通过环转化获得内酰胺：通过用 Zn−AcOH 还原环状 α-叠氮基-β-氧代环戊烷羧酸酯，获得在 δ 位具有环外酯部分的 δ-丁内酰胺。环的转变在还原条件下很容易进行，这是一个前所未有的过程。

  DOI：

  10.1002/ejoc.202300757
• 作为产物：
  描述：

  乙基1-氧亚基-2,3-二氢-1H-茚-2-甲酸基酯 在 sodium azide 、 rosenmund catalyst 、 氢气 、 碘 作用下， 以 水 、 二甲基亚砜 、 异丙醇 为溶剂， 23.0~40.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 生成 ethyl 2-amino-1-oxoindanecarboxylate
  参考文献：
  名称：

  α-氨基-β-氧代酯向 δ-丁内酰胺的环转化

  摘要：

  通过环转化获得内酰胺：通过用 Zn−AcOH 还原环状 α-叠氮基-β-氧代环戊烷羧酸酯，获得在 δ 位具有环外酯部分的 δ-丁内酰胺。环的转变在还原条件下很容易进行，这是一个前所未有的过程。

  DOI：

  10.1002/ejoc.202300757

文献信息

• ACYLAMINO-SUBSTITUTED FUSED CYCLOPENTANECARBOXYLIC ACID DERIVATIVES AND THEIR USE AS PHARMACEUTICALS
  申请人：SCHAEFER Matthias

  公开号：US20110152290A1

  公开（公告）日：2011-06-23

  The present invention relates to compounds of the formula I, wherein A, Y, Z, R 3 to R 6 , R 20 to R 22 and R 50 have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. Specifically, they are inhibitors of the endothelial differentiation gene receptor 2 (Edg-2, EDG2), which is activated by lysophosphatidic acid (LPA) and is also termed as LPA 1 receptor, and are useful for the treatment of diseases such as atherosclerosis, myocardial infarction and heart failure, for example. The invention furthermore relates to processes for the preparation of the compounds of the formula I, their use and pharmaceutical compositions comprising them.

  本发明涉及式I的化合物，其中A、Y、Z、R3至R6、R20至R22和R50具有所述权利要求中指示的含义，这些化合物是有价值的药物活性化合物。具体来说，它们是内皮分化基因受体2（Edg-2，EDG2）的抑制剂，该受体被溶血磷脂酸（LPA）激活，也称为LPA1受体，可用于治疗动脉粥样硬化、心肌梗塞和心力衰竭等疾病。本发明还涉及制备式I化合物的方法、它们的用途以及包含它们的药物组合物。
• Acylamino-substituted fused cyclopentanecarboxylic acid derivatives and their use as pharmaceuticals
  申请人：Schaefer Matthias

  公开号：US08362073B2

  公开（公告）日：2013-01-29

  The present invention relates to compounds of the formula I, wherein A, Y, Z, R3 to R6, R20 to R22 and R50 have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. Specifically, they are inhibitors of the endothelial differentiation gene receptor 2 (Edg-2, EDG2), which is activated by lysophosphatidic acid (LPA) and is also termed as LPA1 receptor, and are useful for the treatment of diseases such as atherosclerosis, myocardial infarction and heart failure, for example. The invention furthermore relates to processes for the preparation of the compounds of the formula I, their use and pharmaceutical compositions comprising them.

  本发明涉及公式I的化合物，其中A，Y，Z，R3至R6，R20至R22和R50具有所述索引中指示的含义，它们是有价值的药物活性化合物。具体来说，它们是内皮分化基因受体2（Edg-2，EDG2）的抑制剂，该受体被溶血磷脂酸（LPA）激活，也称为LPA1受体，对于治疗动脉粥样硬化、心肌梗死和心力衰竭等疾病有用。本发明还涉及制备公式I化合物的方法、它们的使用以及包含它们的药物组合物。
• Radical Chain Reactions of α-Azido-β-keto Esters with Tributyltin Hydride. A Novel Entry to Amides and Lactams through Regiospecific Nitrogen Insertion
  作者：Luisa Benati、Daniele Nanni、Corrado Sangiorgi、Piero Spagnolo

  DOI：10.1021/jo990837g

  日期：1999.10.1

  A variety of acyclic and carbocyclic alpha-azido-beta-keto esters have been readily prepared from the parent dicarbonyl compounds, and their radical chain reactions with tributyltin hydride have been investigated. These reactions normally result in efficient production of alkoxycarbonyl-substituted amides and lactams and thence provide a new, useful method for regiospecific nitrogen insertion of keto ester compounds. The likely mechanism entails initial addition of tributylstannyl radical to the azido moiety to give a stannylaminyl radical, which readily undergoes intramolecular three-membered cyclization onto the ketone group to form an alkoxyl radical. The alkoxyl radical then undergoes regiospecific beta-scissian to form a stable ring-opened radical that is eventually reduced by tributyltin hydride to propagate the chain. With certain substrates, concomitant deazidation occurs to an important extent. This process, which is unusually observed in radical reactions of alkyl azides, is ascribed to addition of the stannyl radical to the terminal azido nitrogen; subsequent fragmentation of the ensuing 1,3-triazenyl adduct gives stannyl azide and a deazidated alkyl radical, resonance-stabilized by the adjacent carbonyl groups. The radical reactions of 2-azido-2-(ethoxy-carbonyl)-1-tetralone with allyltributylstannane and allyltriphenylstannane have also been investigated with the (missed) aim to achieve nitrogen insertion and concomitant allylation.
• US8362073B2
  申请人：——

  公开号：US8362073B2

  公开（公告）日：2013-01-29
• US8445530B2
  申请人：——

  公开号：US8445530B2

  公开（公告）日：2013-05-21