2-氨基-3-(4-甲氧基苯基)丙酸乙酯盐酸盐 | 79751-43-2

• 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
• 中文名称: 2-氨基-3-(4-甲氧基苯基)丙酸乙酯盐酸盐
• 英文名称: D,L-O-methyltyrosine ethyl ester hydrochloride
• 英文别名: 2-amino-3-(4-methoxyphenyl)propionic acid ethyl ester hydrochloride；Ethyl 2-amino-3-(4-methoxyphenyl)propanoate Hydrochloride；ethyl 2-amino-3-(4-methoxyphenyl)propanoate;hydrochloride
• CAS: 79751-43-2；6330-11-6
• 化学式: C₁₂H₁₇NO₃*ClH
• 分子量: 259.733
• InChiKey: FLMKCSGNZMMXDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  61.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-氨基-3-(4-甲氧基苯基)丙酸乙酯盐酸盐 在 五氯化磷 、 三乙胺 、 乙酰氯 作用下， 以 乙酸乙酯 为溶剂， 反应 7.0h， 生成 2-{2-[(1H-indole-2-carbonyl)amino]benzoylamino}-3-(4-methoxyphenyl)propionic acid ethyl ester
  参考文献：
  名称：

  Anthranilic acid based CCK1 receptor antagonists: preliminary investigation on their second “touch point”

  摘要：

  In this phase of structure-affinity relationship study of VL-0395, a new anthranilic acid based CCK1 selective antagonist, we propose a series Of Unnatural aminoacidic derivatives. The result of this work is the identification of a new CCK ligand, which possesses an affinity (IC50 = 35 nm) one order of magnitude greater than the lead and, as a general rule, it points out how the hypothesized receptorial pocket which accommodates the Phe residue allows much more structural modification than that interacting with the N-terminal group. Hence, the modification of the C-terminal pharmacophoric group of our lead VL-0395 can not only enhance the affinity of anthranific acid derivatives but can modulate the selectivity for one CCK receptor subtype or afford mixed antagonists. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.01.002
• 作为产物：
  描述：

  2-乙酰氨基-2-(4-甲氧基苄基)丙二酸二乙酯 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 2-氨基-3-(4-甲氧基苯基)丙酸乙酯盐酸盐
  参考文献：
  名称：

  Anthranilic acid based CCK1 receptor antagonists: preliminary investigation on their second “touch point”

  摘要：

  In this phase of structure-affinity relationship study of VL-0395, a new anthranilic acid based CCK1 selective antagonist, we propose a series Of Unnatural aminoacidic derivatives. The result of this work is the identification of a new CCK ligand, which possesses an affinity (IC50 = 35 nm) one order of magnitude greater than the lead and, as a general rule, it points out how the hypothesized receptorial pocket which accommodates the Phe residue allows much more structural modification than that interacting with the N-terminal group. Hence, the modification of the C-terminal pharmacophoric group of our lead VL-0395 can not only enhance the affinity of anthranific acid derivatives but can modulate the selectivity for one CCK receptor subtype or afford mixed antagonists. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.01.002

文献信息

• A Concise Synthesis of Sterically Hindered 3-Amino-2-Oxindoles
  作者：Stephen J. O’Connor、Zheng Liu

  DOI：10.1055/s-2003-42074

  日期：——

  2-pyridylalanine as the amino acid starting materials, while 3-pyridylalanine and O-methyltyrosine are less efficiently arylated. Sterically hindered amino acids such as valine and phenylglycine are for all practical purposes, not substrates for the key nucleophilic substitution reaction. The resulting 3-alkyl-3-amino-2-oxindoles are important intermediates for the preparation of drug-like substances.

  报道了一种合成 3-烷基-3-氨基-2-羟吲哚的新方法。这些化合物是通过碱介导的亚苄基亚胺保护的 α-氨基酯与 2-硝基氟苯的亲核加成以 3 步法制备的。该方法以1-24%的产率提供了多种3-烷基-3-氨基-2-羟吲哚类似物。以丙氨酸、苯丙氨酸和 2-吡啶基丙氨酸为氨基酸起始原料的产率最高，而 3-吡啶基丙氨酸和 O-甲基酪氨酸的芳基化效率较低。空间位阻氨基酸如缬氨酸和苯基甘氨酸可用于所有实际用途，而不是关键亲核取代反应的底物。所得的 3-烷基-3-氨基-2-羟吲哚是制备类药物的重要中间体。
• Asymmetric catalytic alkynylation of thiazolones and azlactones for synthesis of quaternary α-amino acid precursors
  作者：Beibei Meng、Qian Shi、Yuan Meng、Jie Chen、Weiguo Cao、Xiaoyu Wu

  DOI：10.1039/d1ob00582k

  日期：——

  Asymmetric alkynylation of thiazolones and azlactones with alkynylbenziodoxolones as the electrophilic alkyne source catalyzed by thiourea phosphonium salt is described. By using thiazolones as nucleophiles, the desired alkyne functionalized thiazolones were obtained in 55–89% yields with 31–86% ee. Azlactones gave the desired products in comparable yields with lower enantioselectivities. Ring-opening

  描述了硫脲鏻盐催化的噻唑酮和吖内酯的不对称炔基化反应，其中炔基苯并氧唑酮作为亲电炔烃源。通过使用噻唑酮作为亲核试剂，以 55-89% 的产率和 31-86% 的 ee 获得所需的炔烃官能化噻唑酮。Azlactones 以较低的对映选择性以相当的产率得到所需的产物。炔基化产物的开环导致α，α-二取代的α-氨基酸衍生物有效而不会损失对映选择性。