ethyl 3-amino-3-(o-tolyl)propanoate | 21464-57-3

• 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 3-amino-3-(o-tolyl)propanoate
• 英文别名: 3-Amino-3-(2-tolyl)-propionsaeure-ethylester；Ethyl 3-amino-3-(2-methylphenyl)propanoate
• CAS: 21464-57-3
• 化学式: C₁₂H₁₇NO₂
• mdl: MFCD03839215
• 分子量: 207.272
• InChiKey: MPRYVFLHNZNJLM-UHFFFAOYSA-N

物化性质

• 沸点：
  318.2±30.0 °C(Predicted)
• 密度：
  1.057±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 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 3-amino-3-(o-tolyl)propanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 gamma-氨基-2-甲基苯丙醇
  参考文献：
  名称：

  2-氨基-5,6-二氢-4H-1,3-噻嗪的新合成

  摘要：

  描述了通过用酸处理 2-叔丁基氨基-二氢噻嗪 6、N-γ-羟丙基-N'-叔丁基-硫脲 11 或 2-酰氨基-二氢噻嗪 14 来制备 2-氨基-二氢噻嗪 4。

  DOI：

  10.1002/ardp.19683011006
• 作为产物：
  描述：

  2-甲基苯乙烯 在 盐酸 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 ethyl 3-amino-3-(o-tolyl)propanoate
  参考文献：
  名称：

  Enzymatic preparation of (S)-3-amino-3-(o-tolyl)propanoic acid, a key intermediate for the construction of Cathepsin inhibitors

  摘要：

  Enantiomerically pure (S)-3-amino-3-(o-tolyl)propanoic acid [(S)-6], identified as the preferred enantiomeric form for the construction of novel beta-amino acid derivatives as inhibitors of Cathepsin, was prepared through both indirect and direct enzymatic strategies. Resolution of hydroxymethylated beta-lactam (+/-)-1 through Burkholderia cepacia lipase PSIM-catalysed R-selective butyrylation (E > 200) was first carried out in t-BuOMe. Treatment of the unreacted (S)-1 with 18% HCl then furnished the desired (S)-6 center dot HCl. Next, Candida antarctica lipase B catalysed the ring cleavage of racemic 4-(o-tolyl)azetidin-2-one [(+/-)-2] with excellent R enantioselectivity (E > 200), either in t-BuOMe with added H2O as nucleophile or in H2O at 60 degrees C. Hydrolysis of the less reactive beta-lactam enantiomer [(S)-2] with 18% HCl afforded (S)-6 center dot HCl. A direct enzymatic route to enantiomeric (S)-6 was finally optimized through the lipase PSIM-catalysed S-enantioselective (E>200) hydrolysis of racemic ethyl 3-amino-3-(o-tolyl)propanoate [(+/-)-3] in t-BuOMe with added H2O at 45 degrees C or in H2O at 3 degrees C. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.04.001

文献信息

• [EN] SUBSTITUTED 3-HETEROAROYLAMINO-PROPIONIC ACID DERIVATIVES AND THEIR USE AS PHARMACEUTICALS<br/>[FR] DÉRIVÉS SUBSTITUÉS DE L'ACIDE 3-HÉTÉROAROYLAMINO-PROPIONIQUE ET LEUR UTILISATION COMME COMPOSÉS PHARMACEUTIQUES
  申请人：SANOFI SA

  公开号：WO2012101197A1

  公开（公告）日：2012-08-02

  The present invention relates to compounds of the formula (I), wherein A, D, E, L, G, R10, R30, R40, R50 and R60 have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. They are inhibitors of the protease cathepsin A, and are useful for the treatment of diseases such as atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases, 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、D、E、L、G、R10、R30、R40、R50和R60具有所述权利要求中指示的含义，它们是有价值的药物活性化合物。它们是蛋白酶卡特普西A的抑制剂，可用于治疗动脉硬化、心力衰竭、肾脏疾病、肝脏疾病或炎症性疾病等疾病。本发明还涉及式(I)化合物的制备方法、它们的用途以及包含它们的药物组合物。
• SUBSTITUTED 3-HETEROAROYLAMINO-PROPIONIC ACID DERIVATIVES AND THEIR USE AS PHARMACEUTICALS
  申请人：RUF Sven

  公开号：US20120252809A1

  公开（公告）日：2012-10-04

  The present invention relates to compounds of the formula I, wherein A, D, E, L, G, R 10 , R 30 , R 40 , R 50 and R 60 have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. They are inhibitors of the protease cathepsin A, and are useful for the treatment of diseases such as atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases, 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、D、E、L、G、R10、R30、R40、R50和R60具有声明中指示的含义，它们是有价值的药物活性化合物。它们是蛋白酶卡特普西林A的抑制剂，可用于治疗动脉硬化、心力衰竭、肾脏疾病、肝脏疾病或炎症性疾病等疾病。此外，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制药组合物。
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