3-甲酰基-2-甲氧基苯甲酸甲酯 | 91715-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-甲酰基-2-甲氧基苯甲酸甲酯
• 中文别名: 3-甲醛基-2-甲氧基苯甲酸甲酯
• 英文名称: 3-Formylmethyl-salicylsaeure-methylester
• 英文别名: Methyl 2-hydroxy-3-(2-oxoethyl)benzoate
• CAS: 91715-56-9
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: DHBOYPJJPTYSLG-UHFFFAOYSA-N

物化性质

• 沸点：
  315.9±32.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  3-甲酰基-2-甲氧基苯甲酸甲酯 在 lithium aluminium tetrahydride 、 草酰氯 、 硫酸 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯二氟甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 苯并[b]呋喃-7-甲醛
  参考文献：
  名称：

  BENZODIOXOLE, BENZOFURAN, DIHYDROBENZOFURAN, AND BENZODIOXANE MELATONERGIC AGENTS

  摘要：

  公开号：

  EP1027043B1
• 作为产物：
  描述：

  3-烯丙基-2-羟基苯甲酸甲酯 在 二甲基硫 、 臭氧 作用下， 生成 3-甲酰基-2-甲氧基苯甲酸甲酯
  参考文献：
  名称：

  Aminoalkylindoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics

  摘要：

  Aminoalkylindoles (AAIs) are a novel series of cannabinoid receptor ligands. In this report we disclose the structural features of AAIs which are important for binding to this receptor as measured by inhibition of binding of [H-3]Win 55212-2 (5). Functional activity in the mouse vas deferens is also noted and used to distinguish agonists from potential antagonists. The key structural features for potent cannabinoid activity in this series are a bicyclic (naphthyl) substituent at the 3-position, a small (II) substituent at the 2-position, and an aminoethyl (morpholinoethyl) substituent at the 1-position. A 6-bromo analog, Win 54461 (31), has been identified as a potential cannabinoid receptor antagonist. Modeling experiments were done to develop a pharmacophore and also to compare AAI structures with those of classical cannabinoids. The fact that the cannabinoid AAIs arose out of work on a series of cyclooxygenase inhibitors makes sense now that an endogenous cannabinoid ligand has been identified which is a derivative of arachidonic acid. Because of their unique structures and physical properties, AAIs provide useful tools to study the structure and function of the cannabinoid receptor(s).

  DOI：

  10.1021/jm00016a013

文献信息

• BENZODIOXOLE, BENZOFURAN, DIHYDROBENZOFURAN, AND BENZODIOXANE MELATONERGIC AGENTS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1027043B1

  公开（公告）日：2004-11-10
• Aminoalkylindoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics
  作者：Michael A. Eissenstat、Malcolm R. Bell、Thomas E. D'Ambra、E. John Alexander、Sol J. Daum、James H. Ackerman、Monte D. Gruett、Virendra Kumar、Kimberly G. Estep

  DOI：10.1021/jm00016a013

  日期：1995.8

  Aminoalkylindoles (AAIs) are a novel series of cannabinoid receptor ligands. In this report we disclose the structural features of AAIs which are important for binding to this receptor as measured by inhibition of binding of [H-3]Win 55212-2 (5). Functional activity in the mouse vas deferens is also noted and used to distinguish agonists from potential antagonists. The key structural features for potent cannabinoid activity in this series are a bicyclic (naphthyl) substituent at the 3-position, a small (II) substituent at the 2-position, and an aminoethyl (morpholinoethyl) substituent at the 1-position. A 6-bromo analog, Win 54461 (31), has been identified as a potential cannabinoid receptor antagonist. Modeling experiments were done to develop a pharmacophore and also to compare AAI structures with those of classical cannabinoids. The fact that the cannabinoid AAIs arose out of work on a series of cyclooxygenase inhibitors makes sense now that an endogenous cannabinoid ligand has been identified which is a derivative of arachidonic acid. Because of their unique structures and physical properties, AAIs provide useful tools to study the structure and function of the cannabinoid receptor(s).