(3aS,7aS)-2,2-dimethyltetrahydrobenzo[1,3]dioxol-4-on | 125711-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,7aS)-2,2-dimethyltetrahydrobenzo[1,3]dioxol-4-on
• 英文别名: cis-2,2-dimethyl-hexahydro-2H-1,3-benzodioxol-4-one；(3aS,7aS)-2,2-dimethyl-5,6,7,7a-tetrahydro-3aH-1,3-benzodioxol-4-one
• CAS: 125711-87-7
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: MRTKVCOALNIMRT-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,7aS)-2,2-dimethyltetrahydrobenzo[1,3]dioxol-4-on 在 氢气 作用下， 以 甲醇 为溶剂， 生成 (+/-)-(2S,3S)-2,3-dihydroxycyclohexanone
  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 sodium hydroxide 、 重铬酸吡啶 、 phosphate buffer 作用下， 以 二氯甲烷 为溶剂， 生成 (3aS,7aS)-2,2-dimethyltetrahydrobenzo[1,3]dioxol-4-on
  参考文献：
  名称：

  酶法合成1,2,3-环己三醇的手性异亚丙基衍生物

  摘要：

  2,3-O-异亚丙基-1-环己醇手性结构单元的制备是通过酶解其外消旋的乙酸酯或丁酸正丁酯而获得的高对映体纯度。

  DOI：

  10.1016/s0040-4039(00)99201-3

文献信息

• Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis-Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles
  作者：D. R. Boyd、N. D. Sharma、M. Kaik、M. Bell、M. V. Berberian、P. B. A. McIntyre、B. Kelly、C. Hardacre、P. J. Stevenson、C. C. R. Allen

  DOI：10.1002/adsc.201100273

  日期：2011.9

  Enantiopure arene cis‐tetrahydrodiols of bromobenzene and iodobenzene have been obtained in good yields, from chemoselective hydrogenation (rhodium‐graphite) of the corresponding cis‐dihydrodiol metabolites. Palladium‐catalysed substitution of the halogen, by hydrogen, boron, nitrogen and phosphorus nucleophiles, in the acetonide derivatives, has yielded highly functionalised products for application

  通过对相应的顺式-二氢二醇代谢物进行化学选择性加氢（铑-石​​墨），可以得到高纯度的对映纯的溴苯和碘苯的芳烃顺式-四氢二醇。钯在丙酮化物衍生物中被氢，硼，氮和磷亲核试剂催化的卤素取代产生了高度功能化的产品，可用于合成，具有作为手性配体支架的潜力。
• DUMORTIER, L.;EYCKEN, J. VAN DER;VANDEWALLE, M., TETRAHEDRON LETT., 30,(1989) N4, C. 3201-3204
  作者：DUMORTIER, L.、EYCKEN, J. VAN DER、VANDEWALLE, M.

  DOI：——

  日期：——