Butyric acid (3aR,4S,7aR)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester | 959143-91-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Butyric acid (3aR,4S,7aR)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester
• CAS: 959143-91-0
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: IUVVUNGJMDDGQM-UMNHJUIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Butyric acid (3aR,4S,7aR)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (+/-)-2,2-dimethyl-(3ar,7ac)-hexahydro-benzo[1,3]dioxol-4t-ol
  参考文献：
  名称：

  Conformationally constrained analogues of 2-arachidonoylglycerol

  摘要：

  Novel monocyclic analogues of 2-arachidonoylglycerol (2-AG) were designed in order to explore the pharillacophoric conformations of this endocannabinoid ligand at the key cannabinergic proteins. All 2-arachidonoyl esters of 1,2,3-cyclohexanetriol [meso-7 (AM5504), ()+/- 8 (AM5503), and ineso-9 (AM5505)] were synthesized by regioselective acylation of 2,3-dihydroxycyclohexanone followed by selective reductions. The optically active isomers (+)-8 (AM4434) and (-)-8 (AM4435) were synthesized from (2S,3S)- and (2R,3R)-2,3-dihydroxycyclohexanone, respectively, via a chernoenzymatic route. These head group constrained and conformationally restricted analogues of 2-AG as well as the 1-keto precursors were evaluated as substrates for the endocannabinoid deactivating hydrolytic enzymes monoacylglycerol lipase (MGL) and fatty acid amide hydrolase (FAAH), and also were tested for their affinities for CBI and CB2 cannabinoid receptors. The observed biochemical differences between these ligands can help define the conformational requirements for 2-AG activity at each of the above endocannabinoid protein targets. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.064
• 作为产物：
  描述：

  在 lipase from Candida rugosa 作用下， 以 phosphate buffer 为溶剂， 生成 (3aR,4R,7aS)-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-4-ol 、 Butyric acid (3aR,4S,7aR)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester
  参考文献：
  名称：

  Conformationally constrained analogues of 2-arachidonoylglycerol

  摘要：

  Novel monocyclic analogues of 2-arachidonoylglycerol (2-AG) were designed in order to explore the pharillacophoric conformations of this endocannabinoid ligand at the key cannabinergic proteins. All 2-arachidonoyl esters of 1,2,3-cyclohexanetriol [meso-7 (AM5504), ()+/- 8 (AM5503), and ineso-9 (AM5505)] were synthesized by regioselective acylation of 2,3-dihydroxycyclohexanone followed by selective reductions. The optically active isomers (+)-8 (AM4434) and (-)-8 (AM4435) were synthesized from (2S,3S)- and (2R,3R)-2,3-dihydroxycyclohexanone, respectively, via a chernoenzymatic route. These head group constrained and conformationally restricted analogues of 2-AG as well as the 1-keto precursors were evaluated as substrates for the endocannabinoid deactivating hydrolytic enzymes monoacylglycerol lipase (MGL) and fatty acid amide hydrolase (FAAH), and also were tested for their affinities for CBI and CB2 cannabinoid receptors. The observed biochemical differences between these ligands can help define the conformational requirements for 2-AG activity at each of the above endocannabinoid protein targets. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.064