(S)-2-Amino-3-(3-chloro-phenyl)-propionic acid methyl ester; hydrochloride | 457654-76-1

• 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: (S)-2-Amino-3-(3-chloro-phenyl)-propionic acid methyl ester; hydrochloride
• 英文别名: 3-Chloro-L-phenylalanine methyl ester HCl；methyl (2S)-2-amino-3-(3-chlorophenyl)propanoate;hydrochloride
• CAS: 457654-76-1
• 化学式: C₁₀H₁₂ClNO₂*ClH
• 分子量: 250.125
• InChiKey: QDVSQQKLRHVYFU-FVGYRXGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (S)-2-Amino-3-(3-chloro-phenyl)-propionic acid methyl ester; hydrochloride 在 lithium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 (S)-3-(3-Chloro-phenyl)-2-{[(S)-1-(3,5-dichloro-benzenesulfonyl)-2-methyl-pyrrolidine-2-carbonyl]-amino}-propionic acid
  参考文献：
  名称：

  Substituted N-(3,5-Dichlorobenzenesulfonyl)-l-prolyl-phenylalanine analogues as potent VLA-4 antagonists

  摘要：

  A series of substituted N-(3,5-dichlorobenzenesulfonyl)-L-prolyl- and alpha-methyl-L-prolyl-phenylalanine derivatives was prepared as VLA-4/VCAM antagonists. The compounds showed excellent potency with a wide variety of neutral, polar, electron withdrawing or donating groups on the phenylalanine ring (IC50 similar to I nM). Heteroaryl ring substitution for phenylalanine was also well tolerated. Pharmacokinetic studies in rat were performed on a representative set of compounds in both series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00821-6
• 作为产物：
  描述：

  甲醇 、 3-氯-L-苯丙氨酸 在 氯化亚砜 作用下， 生成 (S)-2-Amino-3-(3-chloro-phenyl)-propionic acid methyl ester; hydrochloride
  参考文献：
  名称：

  Substituted N-(3,5-Dichlorobenzenesulfonyl)-l-prolyl-phenylalanine analogues as potent VLA-4 antagonists

  摘要：

  A series of substituted N-(3,5-dichlorobenzenesulfonyl)-L-prolyl- and alpha-methyl-L-prolyl-phenylalanine derivatives was prepared as VLA-4/VCAM antagonists. The compounds showed excellent potency with a wide variety of neutral, polar, electron withdrawing or donating groups on the phenylalanine ring (IC50 similar to I nM). Heteroaryl ring substitution for phenylalanine was also well tolerated. Pharmacokinetic studies in rat were performed on a representative set of compounds in both series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00821-6

文献信息

• Pd-catalyzed intramolecular C(sp²)–H amination of phenylalanine moieties in dipeptides: synthesis of indoline-2-carboxylate-containing dipeptides
  作者：Yong Zheng、Weibin Song、Yefu Zhu、Bole Wei、Lijiang Xuan

  DOI：10.1039/c8ob00207j

  日期：——

  A palladium-catalyzed intramolecular C(sp2)–H amination of phenylalanine moieties in dipeptides is described. By this protocol, a series of indoline-2-carboxylate-containing dipeptides were synthesized from dipeptides. The N-protected amino acid moiety within the peptide is used as an intrinsic bidentate directing group. This intramolecular C–H amination reaction provides an appealing strategy for

  描述了钯催化二肽中苯丙氨酸分子内的C（sp 2）-H胺化反应。通过该方案，从二肽合成了一系列含吲哚啉-2-羧酸酯的二肽。的Ñ -保护的肽内氨基酸部分被用作内在的二齿定向基团。分子内CH氨基化反应为多肽的合成后修饰提供了一种有吸引力的策略。
• Pd-Catalyzed Site-Selective C(sp²)–H Olefination and Alkynylation of Phenylalanine Residues in Peptides
  作者：Yong Zheng、Weibin Song

  DOI：10.1021/acs.orglett.9b00987

  日期：2019.5.3

  Pd-catalyzed site-selective C(sp2)–H olefination and alkynylation of phenylalanine residues in peptides are described. The amino acids within the peptides are used as native bidentate directing groups to facilitate C–H functionalization. This protocol would provide appealing strategies for the postsynthetic modification of peptides.

  描述了钯催化的位点选择性C（sp 2）–H烯化和肽中苯丙氨酸残基的炔基化反应。肽中的氨基酸用作天然双齿引导基团，以促进C–H功能化。该协议将为多肽的后合成修饰提供有吸引力的策略。