2-Chloro-DL-phenylalanine methyl ester HCl | 37844-15-8

• 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: 2-Chloro-DL-phenylalanine methyl ester HCl
• 英文别名: methyl 2-amino-3-(2-chlorophenyl)propanoate;hydrochloride
• CAS: 37844-15-8
• 化学式: C₁₀H₁₂ClNO₂*ClH
• 分子量: 250.125
• InChiKey: FXIXAZXWVBFVDS-UHFFFAOYSA-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：

  2-Chloro-DL-phenylalanine methyl ester HCl 在 吡啶 、 (1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid diisopropyl ester 、 silver(I) acetate 、 palladium diacetate 、 三乙胺 作用下， 以 二氯甲烷 、 甲基叔丁基醚 为溶剂， 反应 36.0h， 生成 methyl 3-(2-chloro-5-(2-ethoxy-2-oxoethyl)phenyl)-2-(4-nitrophenylsulfonamido)propanoate
  参考文献：
  名称：

  钯（II）/降冰片烯催化元的-C-H烷基化硝基苯磺酰保护的苯丙氨酸

  摘要：

  据报道，以中等至良好的产率，用烷基碘化物进行的Pd /降冰片烯催化的烷基保护的苯基丙氨酸衍生物的直接间烷基化反应。二异丙基双环[2.2.1]庚-5-烯-2,3-二羧酸酯的使用被确定为更合适的瞬态介质。简单的吡啶配体对于该反应的进行也是必不可少的。在该间甲基化反应中未观察到外消旋作用。

  DOI：

  10.1021/acs.joc.8b01933
• 作为产物：
  描述：

  邻氯氯苄 在 盐酸 、 苄基三乙基氯化铵 、 水 、 potassium carbonate 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 2-Chloro-DL-phenylalanine methyl ester HCl
  参考文献：
  名称：

  Synthesis and bioactivity of novel 3-(1-hydroxyethylidene)-5-substituted-pyrrolidine-2,4-dione derivatives

  摘要：

  Ten novel 5-substituted derivatives of 3-(1-hydroxyethylidene)pyrrolidine-2,4-dione were synthesized. The compounds were confirmed by IR, H-1 NMR, MS and elemental analysis. The bioassay indicated that these compounds showed noticeable herbicidal activities, and compounds 6f and 6j exhibited excellent inhibitory activities against the stalk of Echinochloa crusgalli, with EC50 values of 94.4 and 72.7 mg/L, respectively. (C) 2012 Chun Long Yang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.07.002

文献信息

• Oleanolic acid and its derivatives: New inhibitor of protein tyrosine phosphatase 1B with cellular activities
  作者：Yi-Nan Zhang、Wei Zhang、Di Hong、Lei Shi、Qiang Shen、Jing-Ya Li、Jia Li、Li-Hong Hu

  DOI：10.1016/j.bmc.2008.07.080

  日期：2008.9

  Protein tyrosine phosphatase 1B is a key factor in the negative regulation of insulin pathway and a promising target for treatment of diabetes and obesity. Herein, a series of competitive inhibitors were optimized from oleanolic acid, a natural triterpenoid identified against PTP1B by screening libraries of traditional Chinese medicinal herbs. Modifying at 3 and 28 positions, we obtained compound 13

  酪氨酸磷酸酶1B蛋白是胰岛素通路负调节的关键因素，也是治疗糖尿病和肥胖症的有希望的靶标。本文中，通过筛选传统中草药文库中鉴定出的针对PTP1B的天然三萜类化合物齐墩果酸，优化了一系列竞争性抑制剂。在3和28位上进行修饰，我们获得了K（i）为130 nM的化合物13，该化合物在除T细胞蛋白酪氨酸磷酸酶以外的其他与胰岛素途径有关的磷酸酶之间表现出良好的选择性。在细胞模型中的进一步评估表明，这些衍生物增强了CHO / hIR细胞中胰岛素受体的磷酸化作用，并刺激了添加或不添加胰岛素的L6肌管中的葡萄糖摄取。
• Ligand-Enabled <i>meta</i>-Selective C–H Arylation of Nosyl-Protected Phenethylamines, Benzylamines, and 2-Aryl Anilines
  作者：Qiuping Ding、Shengqing Ye、Guolin Cheng、Peng Wang、Marcus E. Farmer、Jin-Quan Yu

  DOI：10.1021/jacs.6b11097

  日期：2017.1.11

  meta-selective C-H arylation of nosyl-protected phenethylamines and benzylamines is disclosed using a combination of norbornene and pyridine-based ligands. Subjecting nosyl protected 2-aryl anilines to this protocol led to meta-C-H arylation at the remote aryl ring. A diverse range of aryl iodides are tolerated in this reaction, along with select heteroaryl iodides. Select aryl bromides bearing ortho-coordinating

  使用降冰片烯和基于吡啶的配体的组合公开了一种 Pd 催化的间位选择性 CH 芳基化的 nosyl 保护的苯乙胺和苄胺。将 nosyl 保护的 2-芳基苯胺置于该协议下导致远程芳环上的间位 CH 芳基化。在该反应中可以耐受各种芳基碘化物，以及精选的杂芳基碘化物。带有邻位配位基团的精选芳基溴也可用作该反应中的有效偶联伙伴。吡啶配体的使用使钯负载降低到 2.5 mol%。此外，首次证明了催化量的 2-降冰片烯 (20 mol%) 来介导该间位 CH 活化过程。
• Haloalkyl containing compounds as cysteine protease inhibitors
  申请人：Link O. John

  公开号：US20050182096A1

  公开（公告）日：2005-08-18

  The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.

  本发明涉及抑制半胱氨酸蛋白酶的化合物，特别是cathepsins B、K、L、F和S，因此可用于治疗由这些蛋白酶介导的疾病。本发明涉及包含这些化合物的药物组合物和制备它们的过程。
• Haloalkyl Containing Compounds as Cysteine Protease Inhibitors
  申请人：Link O. John

  公开号：US20070276019A1

  公开（公告）日：2007-11-29

  The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.

  本发明涉及一种抑制半胱氨酸蛋白酶的化合物，尤其是对B、K、L、F和S型猫蛋白酶具有抑制作用，因此可用于治疗由这些蛋白酶介导的疾病。本发明涉及包含这些化合物的药物组合物以及制备它们的过程。
• Synergistic Catalysis between a Dipeptide Phosphonium Salt and a Metal‐Based Lewis Acid for Asymmetric Synthesis of <i>N</i> ‐Bridged [3.2.1] Ring Systems
  作者：Yuan Chen、Jiajia He、Cheng Zhuang、Zanjiao Liu、Kai Xiao、Zhishan Su、Xiaoyu Ren、Tianli Wang

  DOI：10.1002/anie.202207334

  日期：2022.9.19

  method for asymmetric construction of N-bridged [3.2.1] rings by a phosphonium salt/silver co-catalyzed cyclization has been developed. This route affords fluorine-installed tropane derivatives in excellent stereoselectivities. The mechanistic results revealed that the silver nitrite was installed on the phosphonium salt via hydrogen bonding and simultaneously activated the dipole, in a “sandwich” reaction

  已经开发了一种通过鏻盐/银共催化环化不对称构建N桥 [3.2.1] 环的协同催化方法。该路线以优异的立体选择性提供了氟安装的托烷衍生物。机理结果表明，在“三明治”反应模型中，亚硝酸银通过氢键安装在鏻盐上，同时激活偶极子。