O-methyl-tyrosine methyl ester; hydrochloride | 7479-01-8

• 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: O-methyl-tyrosine methyl ester; hydrochloride
• 英文别名: O-Methyl-tyrosin-methylester; Hydrochlorid；L-Tyrosine, O-methyl-, methyl ester, hydrochloride；methyl 2-amino-3-(4-methoxyphenyl)propanoate;hydrochloride
• CAS: 7479-01-8；64657-63-2；70601-64-8
• 化学式: C₁₁H₁₅NO₃*ClH
• 分子量: 245.706
• InChiKey: CDCIQNBPLQWUQS-UHFFFAOYSA-N

物化性质

• 熔点：
  180-181 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  O-methyl-tyrosine methyl ester; hydrochloride 在 lithium aluminium tetrahydride 、 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 120.0h， 生成 2-(p-methoxybenzyl)ethylenediamine
  参考文献：
  名称：

  Brunner; Kroiss; Schmidt, European Journal of Medicinal Chemistry, 1986, vol. 21, # 4, p. 333 - 338

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2-(benzylideneamino)-3-(4-methoxyphenyl)propanoate 在 盐酸 、 水 作用下， 生成 O-methyl-tyrosine methyl ester; hydrochloride
  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

• Novel <i>N</i>-transfer reagent for converting α-amino acid derivatives to α-diazo compounds
  作者：Guan-Han Lu、Tzu-Chia Huang、Hsiao-Chin Hsueh、Shin-Cherng Yang、Ting-Wei Cho、Ho-Hsuan Chou

  DOI：10.1039/d1cc01285a

  日期：——

  direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides from N-terminal dipeptides (32 examples, up to 91%)

  开发了一种新型通用N-转移试剂，可在温和的碱性条件下直接有效地将 α-氨基酮、乙酰胺和酯转化为相应的 α-重氮产物。这种一步合成方法不仅允许从 α-氨基酸衍生物生成 α-取代-α-重氮羰基化合物，而且允许从N-末端二肽制备 α-重氮二肽（32 个例子，高达 91%） .
• Renin-inhibiting functionalized peptidyl aminodiols and - triols
  申请人：ABBOTT LABORATORIES

  公开号：EP0341602A2

  公开（公告）日：1989-11-15

  A renin inhibiting compound of the formula: or a pharmaceutically acceptable salt, ester or prodrug thereof.

  一个公式为的抑制肾素的化合物： 或其药用可接受的盐、酯或前药。
• A new type of chiral-pyridoxamines for catalytic asymmetric transamination of α-keto acids
  作者：Jianfeng Chen、Junyu Zhao、Xing Gong、Dongfang Xu、Baoguo Zhao

  DOI：10.1016/j.tetlet.2016.09.005

  日期：2016.10

  A new type of chiral pyridoxamines bearing an adjacent chiral stereocenter has been developed via multi-step synthesis. The pyridoxamines displayed catalytic activity in asymmetric transamination of α-keto acids to give a variety of optically active amino acids in 27–78% yields with 34–62% ee’s under very mild conditions. This work provides a synthetic strategy to construct new chiral pyridoxamines

  通过多步合成已经开发了一种新型的带有相邻手性立体中心的手性吡ido胺。吡ido胺在非常温和的条件下，在α-酮酸的不对称转氨反应中显示出催化活性，从而以27-78％的产率提供了34-62％ee的多种光学活性氨基酸。这项工作提供了使用溴吡啶7作为关键合成子来构建新的手性吡ido胺的合成策略，也代表了手性吡x胺在不对称催化中的早期应用实例。
• 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。