methyl β-amino-β-(4-methylphenyl)propionate hydrochloride | 101207-50-5

• 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: methyl β-amino-β-(4-methylphenyl)propionate hydrochloride
• 英文别名: Methyl 3-amino-3-(4-methylphenyl)propanoate hydrochloride；methyl 3-amino-3-(4-methylphenyl)propanoate;hydrochloride
• CAS: 101207-50-5；1234556-74-1
• 化学式: C₁₁H₁₅NO₂*ClH
• mdl: MFCD09834089
• 分子量: 229.707
• InChiKey: VUDNJAZNBRXDQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl β-amino-β-(4-methylphenyl)propionate hydrochloride 在 ammonium hydroxide 作用下， 以 水 为溶剂， 生成 3-Amino-3-(4-methylphenyl)propanamide
  参考文献：
  名称：

  Highly enantioselective enzymatic resolution of aromatic β-amino acid amides with Pd-catalyzed racemization

  摘要：

  The kinetic resolution of an aromatic beta-amino acid amide 3a-d via N-acylation was explored with two lipases, Candida antarctica lipase A (CALA) and Pseudomonas stutzeri lipase (PSL). The PSL-catalyzed resolution proceeded with excellent enantioselectivity (E = >400) to give both acylated products and unreacted substrates in enantiopure forms. Three additional aromatic beta-amino acid amides 3b-d were also resolved by PSL with a high level of enantioselectivity (E = >200). The PSL-catalyzed resolution of 3a was coupled with a Pd-catalyzed racemization to obtain enantiopure N-acylated product (R)-4a (>99% ee) in high yield (90%). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.022
• 作为产物：
  描述：

  甲醇 、 3-氨基-3-(4-甲基苯基)丙酸 在 盐酸 作用下， 反应 15.0h， 生成 methyl β-amino-β-(4-methylphenyl)propionate hydrochloride
  参考文献：
  名称：

  Amidine derivatives and cardiotonic compositions

  摘要：

  式##STR1##中的胺基衍生物，其中R.sub.1和R.sub.2，可以相同也可以不同，分别代表氢原子或低碳基团，或者R.sub.1和R.sub.2与中间的碳原子和/或杂原子一起可以形成环；X代表##STR2##（其中R.sub.8代表氢原子、低碳基团，或--CH.sub.2 COOR.sub.9，其中R.sub.9代表氢原子或低碳基团；Z代表单键，--CH.sub.2 --，--CH.sub.2 CH.sub.2 --，或--CH.dbd.CH--）；R.sub.3代表氢或氯原子，甲氧基，硝基，或氨基；Y代表--CH.sub.2 CH.sub.2 --，--CH.dbd.CH--，--CH.sub.2 O--，或--OCH.sub.2 --；R.sub.4代表氢原子，甲氧基，苯甲酰基，硝基，或氨基；以及R.sub.5，R.sub.6和R.sub.7，可以相同也可以不同，分别代表氢原子，低碳基团，环烷基团，芳基烷基团，取代基烷基团，取代基芳基烷基团，或氨基，或者R.sub.5和R.sub.7可以形成环，或其盐具有优异的心力活性，并可用作心力药。

  公开号：

  US04598077A1

文献信息

• Amidine derivatives and cardiotonic compositions
  申请人：Torii & Co. Ltd.

  公开号：US04598077A1

  公开（公告）日：1986-07-01

  Amidine derivatives of the formula ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, represent each a hydrogen atom or a lower alkyl group, or R.sub.1 and R.sub.2 together with an intermediary carbon atom and/or hetero atom may form a ring; X represents ##STR2## (wherein R.sub.8 represents a hydrogen atom, a lower alkyl group, or --CH.sub.2 COOR.sub.9, where R.sub.9 represents a hydrogen atom or a lower alkyl group; Z represents a single bond, --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, or --CH.dbd.CH--); R.sub.3 represents a hydrogen or chlorine atom, methoxy group, nitro group, or amino group; Y represents --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 O--, or --OCH.sub.2 --; R.sub.4 represents a hydrogen atom, methoxy group, benzoyl group, nitro group, or amino group; and R.sub.5, R.sub.6 and R.sub.7, which may be the same or different, represent each a hydrogen atom, lower alkyl group, cycloalkyl group, aralkyl group, substituted alkyl group, substituted aralkyl group, or amino group, or R.sub.5 and R.sub.7 may form a ring, or salts thereof have an excellent cardiotonic activity and can be used as cardiotonics.

  式##STR1##中的胺基衍生物，其中R.sub.1和R.sub.2，可以相同也可以不同，分别代表氢原子或低碳基团，或者R.sub.1和R.sub.2与中间的碳原子和/或杂原子一起可以形成环；X代表##STR2##（其中R.sub.8代表氢原子、低碳基团，或--CH.sub.2 COOR.sub.9，其中R.sub.9代表氢原子或低碳基团；Z代表单键，--CH.sub.2 --，--CH.sub.2 CH.sub.2 --，或--CH.dbd.CH--）；R.sub.3代表氢或氯原子，甲氧基，硝基，或氨基；Y代表--CH.sub.2 CH.sub.2 --，--CH.dbd.CH--，--CH.sub.2 O--，或--OCH.sub.2 --；R.sub.4代表氢原子，甲氧基，苯甲酰基，硝基，或氨基；以及R.sub.5，R.sub.6和R.sub.7，可以相同也可以不同，分别代表氢原子，低碳基团，环烷基团，芳基烷基团，取代基烷基团，取代基芳基烷基团，或氨基，或者R.sub.5和R.sub.7可以形成环，或其盐具有优异的心力活性，并可用作心力药。
• Synthesis, in Vitro and in Vivo Biological Evaluation, Docking Studies, and Structure−Activity Relationship (SAR) Discussion of Dipeptidyl Boronic Acid Proteasome Inhibitors Composed of β-Amino Acids
  作者：Yongqiang Zhu、Xinrong Zhu、Gang Wu、Yuheng Ma、Yuejie Li、Xin Zhao、Yunxia Yuan、Jie Yang、Sen Yu、Feng Shao、Runtao Li、Yanrong Ke、Aijun Lu、Zhenming Liu、Liangren Zhang

  DOI：10.1021/jm901407s

  日期：2010.3.11

  A series of novel dipeptidyl boronic acid proteasome inhibitors composed of beta-amino acids were synthesized, in vitro and in vivo biologically evaluated, and theoretically modeled for the first time. From the screened racemic compounds in enzyme, 4i wits the most active. The IC50 value of its pure enantiomer 4q was 9.6 nM, 36-fold more active than its isomer 4p and as active its the marketed bortezomib in inhibiting human 20S proteasome. This candidate also showed good activities with IC50 values nearly less than 5 mu M against several human solid and hematologic tumor cell lines. Safety evaluation in vivo with zebrafish and Sprague-Dawley (SD) rats showed that the candidate 4q was less toxic than bortezomib. Pharmacokinetic profiles suggested candidate 4q showed a more plasma exposure and longer half-life than bortezomib. Docking results indicated that 4q nearly interacted with 20S proteasome in it similar way as bortezomib.
• Aspartyl dipeptide amide derivatives and sweeteners
  申请人：Ajinomoto Co., Ltd.

  公开号：EP0818463B1

  公开（公告）日：1999-09-29
• US4598077A
  申请人：——

  公开号：US4598077A

  公开（公告）日：1986-07-01
• US5958496A
  申请人：——

  公开号：US5958496A

  公开（公告）日：1999-09-28