(1R,2R,4R)-p-menthane-1,2,8-triol | 93861-31-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,4R)-p-menthane-1,2,8-triol
• 英文别名: 1,2,8-Trihydroxy-p-menthan；(1R,2R,4R)-4-(2-hydroxypropan-2-yl)-1-methylcyclohexane-1,2-diol
• CAS: 93861-31-5
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: KANCZQSRUGHECB-NQMVMOMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+)-α-松油醇 在 sodium hydroxide 、 甲酸 、 硫酸 、 双氧水 作用下， 反应 24.5h， 生成 (1R,2R,4R)-p-menthane-1,2,8-triol
  参考文献：
  名称：

  Carman, Raymond M.; Fletcher, Mary T., Australian Journal of Chemistry, 1984, vol. 37, # 26, p. 2129 - 2136

  摘要：

  DOI：

文献信息

• Studies on the Oxidation of cis- and trans-Pinane with molecular oxygen
  作者：Thomas Brose、Wilhelm Pritzkow、Gerda Thomas

  DOI：10.1002/prac.19923340506

  日期：——

  The pinanes are preferably attacked at the tertiary C-H bond in 2-position, but' products of the oxidative attack at the secondary C-H bonds in 3- and 4-position are also found. At 100-degrees-C cis-pinane is attacked more easily than trans-pinane (k(cis):k(trans) = 6.4), the relative rates of attack at the secondary C-H bonds in positions 3 and 4 with respect to the tertiary C-H bond in 2-position were also determined (in cis-pinane k(sec):k(tert) = 0.027; in trans-pinane k(sec):k(tert) = 0.20). After the attack at the 2-C-H bond the radical formed can either react with oxygen to form the corresponding cis- and trans-peroxy radicals and further to give cis- and trans-2-hydroperoxy pinane or fragmentate to the monocyclic radical derived from alpha-terpinene, giving as final products alpha-terpinene hydroperoxide and the bicyclic 8-hydroperoxy 4,4,8-trimethyl 2,3-dioxabicyclo[3.3.1]nonane. The corresponding alcohols were found after reduction with sodium sulphite. The oxidation at position 2 of the pinanes delivers not only the cis- and trans-hydroperoxide but also, as short-lived intermediates, the corresponding 2-pinanyloxy radicals. These radicals fragmentate forming a carbon radical with cyclobutane structure whose oxidation products were identified. Besides fragmentation of the 2-pinanyloxy radical also an intramolecular H-transfer from the methyl group in 9-position to the oxygen of the trans-2-pinanyloxy radical takes place leading to 9-hydroperoxy trans-pinane-2-ol.
• Carman, Raymond M.; Fletcher, Mary T., Australian Journal of Chemistry, 1984, vol. 37, # 26, p. 2129 - 2136
  作者：Carman, Raymond M.、Fletcher, Mary T.

  DOI：——

  日期：——