2-(3-hydroxyphenyl)-N-methoxy-N-methylacetamide | 1344214-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-hydroxyphenyl)-N-methoxy-N-methylacetamide
• CAS: 1344214-04-5
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: ZBGBNJICZPKVCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-hydroxyphenyl)-N-methoxy-N-methylacetamide 在 咪唑 、 盐酸 、 正丁基锂 、 硼烷四氢呋喃络合物 、 四丁基氟化铵 、 水 、 sodium hydride 、 对甲苯磺酸 、 三苯基膦 、 sodium hydroxide 、 (R)-2-甲基-CBS-恶唑硼烷 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 13.99h， 生成 4-([2-((2R)-2-((1E,3S)-3-hydroxy-4-[3-(pyridin-3-ylmethoxy)phenyl]but-1-enyl)-5-oxopyrrolidin-1-yl)ethyl]sulfanyl)butanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of γ-lactam analogs of PGE2 as EP4 and EP2/EP4 agonists

  摘要：

  To identify topically effective EP4 agonists and EP2/EP4 dual agonists with excellent subtype selectivity, further optimization of the 16-phenyl omega-chain moiety of the gamma-lactam 5-thia prostaglandin E analog and the 2-mercaptothiazole-4-carboxylic acid analog were undertaken. Rat in vivo evaluation of these newly identified compounds as their poly (lactide-co-glycolide) microsphere formulation, from which sustained release of the test compound is possible, led us to discover compounds that showed efficacy in a rat bone fracture healing model after its topical administration without serious influence on blood pressure and heart rate. A structure-activity relationship study is also presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.008
• 作为产物：
  描述：

  3-羟基苯乙酸 、 二甲羟胺盐酸盐 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以100%的产率得到2-(3-hydroxyphenyl)-N-methoxy-N-methylacetamide
  参考文献：
  名称：

  Synthesis and evaluation of γ-lactam analogs of PGE2 as EP4 and EP2/EP4 agonists

  摘要：

  To identify topically effective EP4 agonists and EP2/EP4 dual agonists with excellent subtype selectivity, further optimization of the 16-phenyl omega-chain moiety of the gamma-lactam 5-thia prostaglandin E analog and the 2-mercaptothiazole-4-carboxylic acid analog were undertaken. Rat in vivo evaluation of these newly identified compounds as their poly (lactide-co-glycolide) microsphere formulation, from which sustained release of the test compound is possible, led us to discover compounds that showed efficacy in a rat bone fracture healing model after its topical administration without serious influence on blood pressure and heart rate. A structure-activity relationship study is also presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.008

文献信息

• Gold-catalyzed construction of two adjacent quaternary stereocenters via sequential C–H functionalization and aldol annulation
  作者：Zhunzhun Yu、Haile Qiu、Lu Liu、Junliang Zhang

  DOI：10.1039/c5cc08880a

  日期：——

  A novel gold-catalyzed intermolecular C–H functionalization and aldol cyclization for the construction of two adjacent quaternary centers is presented.

  一种新颖的金催化的分子间C-H官能化和醛缩环化反应，用于构建两个相邻的四季胺中心。
• Synthesis and evaluation of γ-lactam analogs of PGE2 as EP4 and EP2/EP4 agonists
  作者：Tohru Kambe、Toru Maruyama、Yoshihiko Nakai、Hiroji Oida、Takayuki Maruyama、Nobutaka Abe、Akio Nishiura、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2012.04.008

  日期：2012.6

  To identify topically effective EP4 agonists and EP2/EP4 dual agonists with excellent subtype selectivity, further optimization of the 16-phenyl omega-chain moiety of the gamma-lactam 5-thia prostaglandin E analog and the 2-mercaptothiazole-4-carboxylic acid analog were undertaken. Rat in vivo evaluation of these newly identified compounds as their poly (lactide-co-glycolide) microsphere formulation, from which sustained release of the test compound is possible, led us to discover compounds that showed efficacy in a rat bone fracture healing model after its topical administration without serious influence on blood pressure and heart rate. A structure-activity relationship study is also presented. (C) 2012 Elsevier Ltd. All rights reserved.