methyl (2S)-(methylamino)(phenyl)acetate | 111934-22-6

• 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 (2S)-(methylamino)(phenyl)acetate
• 英文别名: methyl 2-(methylamino)-2-phenylacetate；N-methylphenylglicyne methyl ester；methyl (2S)-2-(methylamino)-2-phenylacetate
• CAS: 111934-22-6
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: MAQULIULLOBHGK-VIFPVBQESA-N

物化性质

• 沸点：
  250.2±28.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 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：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-fluoro-6-(2-((1-hydroxy-3-phenylpropan-2-yl)amino)-2-oxoethoxy)benzoic acid 、 methyl (2S)-(methylamino)(phenyl)acetate 在 N,N-二异丙基乙胺 、 N,N'-羰基二咪唑 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 methyl (2S)-2-[[2-[2-[[(1S)-1-benzyl-2-hydroxy-ethyl]amino]-2-oxo-ethoxy]-6-fluoro-benzoyl]-methyl-amino]-2-phenyl-acetate
  参考文献：
  名称：

  Inhibitors of hepatitis C virus polymerase: Synthesis and characterization of novel 2-oxy-6-fluoro-N-((S)-1-hydroxy-3-phenylpropan-2-yl)-benzamides

  摘要：

  SAR exploration from an initial hit, (S)-N-(2-cyclohexenylethyl)-2-fluoro-6-(2-(1-hydroxy-3-phenylpropan-2-ylamino)-2-oxoethoxy)benzamide (1), identified using our proprietary automated ligand identification system (ALIS),(1) has led to a novel series of selective hepatitis C virus (HCV) NS5B polymerase inhibitors with improved in vitro potency as exemplified by (S)-2-fluoro-6-(2-(1-hydroxy-3-phenylpropan-2-ylamino)-2-oxoethoxy)-N-isopentyl-N-methylbenzamidecarboxamide (41) (IC(50) = 0.5 mu M). The crystal structure of an analogue (44) was solved and provided rationalization of the SAR of this series, which binds in a distinct manner in the palm domain of NS5B, consistent with biochemical analysis using enzyme mutant variants. These data warrant further lead optimization efforts on this novel series of non-nucleoside inhibitors targeting the HCV polymerase. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.054
• 作为产物：
  描述：

  (S)-(+)-2-苯甘氨酸甲酯 盐酸盐 在 三乙基硅烷 、 三氟乙酸 作用下， 以 氯仿 、 水 为溶剂， 反应 20.5h， 生成 methyl (2S)-(methylamino)(phenyl)acetate
  参考文献：
  名称：

  Immonium ion based synthetic methodology: a novel method for the N-methylation of dipeptides and amino acid derivatives via retro aza Diels-Alder reactions

  摘要：

  DOI：

  10.1021/jo00235a021

文献信息

• Direct Synthesis of <i>N</i>-Alkyl Arylglycines by Organocatalytic Asymmetric Transfer Hydrogenation of <i>N</i>-Alkyl Aryl Imino Esters
  作者：Javier Mazuela、Thomas Antonsson、Magnus J. Johansson、Laurent Knerr、Stephen P. Marsden

  DOI：10.1021/acs.orglett.7b02627

  日期：2017.10.20

  The organocatalytic asymmetric transfer hydrogenation of N-alkyl aryl imino esters for the direct synthesis of N-alkylated arylglycinate esters is reported. High yields and enantiomeric ratios were obtained, and tolerance to a diverse set of functional groups facilitated the preparation of more complex molecules as well as intermediates for active pharmaceuticals. A simple recycling protocol was developed

  报道了用于直接合成N-烷基化的芳基甘氨酸酯的有机催化的N-烷基芳基亚氨基亚氨基酯的不对称转移氢化。获得了高产率和对映体比率，并且对各种官能团的耐受性促进了更复杂的分子以及活性药物中间体的制备。针对布朗斯台德酸催化剂开发了一种简单的回收方案，该方案可以通过五个循环重复使用，而不会损失活性或选择性。
• SYNTHESIS OF FUNCTIONALIZED OCTAHYDRO-ISOQUINOLIN-1-ONE-8-CARBOXYLIC ESTERS AND ANALOGS, AND THERAPEUTIC METHODS
  申请人：University of Kansas

  公开号：US20140243333A1

  公开（公告）日：2014-08-28

  A functionalized polycyclic compound can have a structure of Formula 1 or salt, prodrug, analog, or derivative thereof, which compound can be prepared by providing a diene; reacting the diene with a dienophile under sufficient conditions for a combined Diels-Alder/acylation reaction so as to provide a polycyclic compound having a carboxylic acid; and coupling the carboxylic acid with an amine-containing compound or a hydroxyl-containing compound so as to form an amide or an ester and producing a compound having a structure of Formula 1. The compound can be used for modulating an opioid receptor, which can be conducted by administering to an opioid receptor a functionalized polycyclic compound as described herein in an effective amount to modulate the functionality of the opioid receptor. Such opioid modulation can provide a biological benefit to a subject.

  一种功能化多环化合物可以具有公式1或其盐、前药、类似物或衍生物的结构，该化合物可以通过提供二烯；在足够条件下将二烯与二烯丙酮反应，从而提供具有羧酸的多环化合物，并将羧酸与含胺化合物或含羟基化合物偶联，以形成酰胺或酯，并产生具有公式1结构的化合物进行制备。该化合物可用于调节阿片受体，这可通过向阿片受体中施用本文所述的功能化多环化合物的有效量来进行，以调节阿片受体的功能。这种阿片调节可以为主体提供生物学上的益处。
• COMPOUNDS FOR INHIBITING DRUG-RESISTANT STRAINS OF HIV-1 INTEGRASE
  申请人：THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SEC., DEPT. OF HEALTH AND HUMAN SERVICES

  公开号：US20160083382A1

  公开（公告）日：2016-03-24

  A method of inhibiting drug-resistant HIV-1 integrase in a subject comprising administering to a subject in need thereof a therapeutically effective amount of a compound of formula I, or a pharmaceutically acceptable salt or ester thereof, having a structure of: wherein X is N, C(OH), or CH; Y is H or OH; each of Z 1 -Z 5 is independently H or halogen; R 4 is H, OH, NH 2 , NHR 8 , NR 8 R 9 or R 8 ; R 5 , R 6 , and R 7 is each independently H, halogen, OR 8 , R 8 , NHR 8 , NR 8 R 9 , CO 2 R 8 , CONR 8 R 9 , SO 2 NR 8 R 9 , or R 5 and R 6 together with the carbon atoms to which R 5 and R 6 are attached form an optionally-substituted carbocycle or optionally-substituted heterocycle; and R 8 and R 9 is each independently H, optionally-substituted alkyl, optionally-substituted alkenyl, optionally-substituted alkynyl, optionally-substituted aryl, optionally-substituted cycloalkyl, optionally-substituted cycloalkylene, optionally-substituted heterocycle, optionally-substituted amide, optionally-substituted ester, or R 8 and R 9 together with the nitrogen to which R 8 and R 9 are attached form an optionally-substituted heterocycle.

  本方法涉及在需要抑制药物耐药性HIV-1整合酶的主体中向其施用公式I的化合物的治疗有效量，或其药学上可接受的盐或酯，其结构为：其中X为N，C（OH）或CH；Y为H或OH；Z1-Z5中的每一个独立为H或卤素；R4为H，OH，NH2，NHR8，NR8R9或R8；R5、R6和R7各自独立为H，卤素，OR8，R8，NHR8，NR8R9，CO2R8，CONR8R9，SO2NR8R9或R5和R6与R5和R6附着的碳原子一起形成可选地取代的碳环或可选地取代的杂环；R8和R9各自独立为H，可选地取代的烷基，可选地取代的烯基，可选地取代的炔基，可选地取代的芳基，可选地取代的环烷基，可选地取代的环烷基，可选地取代的杂环，可选地取代的酰胺，可选地取代的酯，或R8和R9与R8和R9附着的氮一起形成可选地取代的杂环。
• METHOD FOR PRODUCING CARBOXYLIC ACID AND ALCOHOL BY HYDROLYSIS OF ESTER
  申请人：National University Corporation Nagoya University

  公开号：EP2799422A1

  公开（公告）日：2014-11-05

  As shown by the following formula (1), after methyl laurate (2 mmol) and water (8 mL) are added to an ammonium pyrosulfate catalyst (5 mol%), a hydrolysis reaction of methyl laurate is carried out by heating for 24 hours at 60°C while stirring is performed, so that lauric acid can be obtained with a yield of 86%.

  如下式（1）所示，向焦硫酸铵催化剂（5 摩尔%）中加入月桂酸甲酯（2 毫摩尔）和水（8 毫升）后，在 60°C 下搅拌加热 24 小时，进行月桂酸甲酯的水解反应，可获得产率为 86%的月桂酸。
• GRIECO, PAUL A.;BAHSAS, ALI, J. ORG. CHEM., 52,(1987) N 26, 5746-5749
  作者：GRIECO, PAUL A.、BAHSAS, ALI

  DOI：——

  日期：——