(+/-)-2,2-dimethyl-(3ar,7ac)-hexahydro-benzo[1,3]dioxol-4t-ol | 81225-67-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-2,2-dimethyl-(3ar,7ac)-hexahydro-benzo[1,3]dioxol-4t-ol
• 英文别名: (3aS,4S,7aR)-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-4-ol
• CAS: 81225-67-4；125627-39-6；125627-45-4；125627-51-2；125627-53-4；125711-73-1；125711-75-3；125711-77-5；125760-50-1；140224-90-4；146388-17-2
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: GWCAZIJIJCFJCT-RNJXMRFFSA-N

物化性质

• 沸点：
  98 °C(Press: 5 Torr)
• 密度：
  1.088±0.06 g/cm3(Predicted)

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：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2,2-dimethyl-(3ar,7ac)-hexahydro-benzo[1,3]dioxol-4t-ol 在 戴斯-马丁氧化剂 作用下， 生成 (3aR,7aR)-2,2-dimethylperhydro-1,3-benzodioxol-4-one
  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：

  (3aR,7aR)-2,2-dimethylperhydro-1,3-benzodioxol-4-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到(+/-)-2,2-dimethyl-(3ar,7ac)-hexahydro-benzo[1,3]dioxol-4t-ol
  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

• STUDIES IN THE POLYOXYPHENOL SERIES: V. PREPARATION FROM PYROGALLOL OF THE ISOMERIC CYCLOHEXANE-1,2,3-TRIOLS AND -1,2-DIOLS, AND OF SEVERAL ISOPROPYLIDENE AND MONOMETHYL DERIVATIVES
  作者：W. R. Christian、C. J. Gogek、C. B. Purves

  DOI：10.1139/v51-106

  日期：1951.11.1

  A study of the high pressure hydrogenation of pyrogallol over nickel, copper – chromium oxide, and palladium catalysts showed that yields of 35% to about 60% of cis-cis-cis-cyclohexane-l,2,3-triol ...

  对连苯三酚在镍、铜-氧化铬和钯催化剂上高压加氢的研究表明，顺式-顺式-顺式-环己烷-1,2,3-三醇的产率为 35% 至约 60%。