(+)-(3S,4S)-p-mentha-1,8(10)-diene-3,9-diol | 204916-69-8

• 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: (+)-(3S,4S)-p-mentha-1,8(10)-diene-3,9-diol
• 英文别名: (+)-(3S,4S)-p-mentha-1,8(10)diene-3,9-diol；(+)-(1S,2S)-2-hydroxy-4-methyl-β-methylenecyclohex-3-eneethanol；(1S,2S)-2-hydroxy-4-methyl-β-methylenecyclohex-3-ene-1-ethanol；(1S,6S)-6-(3-hydroxyprop-1-en-2-yl)-3-methylcyclohex-2-en-1-ol
• CAS: 204916-69-8
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: GCLZPPYBYFYOCA-UWVGGRQHSA-N

物化性质

• 熔点：
  72 °C
• 沸点：
  272.1±40.0 °C(Predicted)
• 密度：
  1.066±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：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(3S,4S)-p-mentha-1,8(10)-diene-3,9-diol 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以94%的产率得到(-)-(3S,4S)-3,9-epoxy-p-mentha-1,8(10)-diene
  参考文献：
  名称：

  Enzyme-Mediated Preparation of Enantiomerically Pure p-Menthan- 3,9-diols and Their Use for the Synthesis of Natural p-Menthane Lactones and Ethers

  摘要：

  The diasiereoselective preparation of the p-menthane-3,9-diols (+/-)-12, (+/-)-13a, (+/-)-13b, and (+/-)-18 and the study of their enzymic resolution is described (Scheme 1). The corresponding enantiomer-enriched diols obtained by means of the lipase-mediated kinetic acetylation of the racemic diols are suitable synthetic precursors of many relevant p-menthane monoterpenes. Their usefulness is shown in the preparation of different natural products of this class that are interesting for industrial purposes because of their odor qualities, i.e., of the enantiomeric form of 3-hydroxy-p-menthan-9-oic acid lactone 1, of mintlactone 2, of the 3,9-epoxy-p-menth-1,8(10)-diene 10, and of the pheromone vesperal 11 (Schemes 2 and 3).

  DOI：

  10.1002/1522-2675(200208)85:8<2489::aid-hlca2489>3.0.co;2-9
• 作为产物：
  描述：

  (+)-(3S,4S)-p-mentha-1,8(10)diene-3,9-diol 9-acetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以93%的产率得到(+)-(3S,4S)-p-mentha-1,8(10)-diene-3,9-diol
  参考文献：
  名称：

  Enzyme-Mediated Preparation of Enantiomerically Pure p-Menthan- 3,9-diols and Their Use for the Synthesis of Natural p-Menthane Lactones and Ethers

  摘要：

  The diasiereoselective preparation of the p-menthane-3,9-diols (+/-)-12, (+/-)-13a, (+/-)-13b, and (+/-)-18 and the study of their enzymic resolution is described (Scheme 1). The corresponding enantiomer-enriched diols obtained by means of the lipase-mediated kinetic acetylation of the racemic diols are suitable synthetic precursors of many relevant p-menthane monoterpenes. Their usefulness is shown in the preparation of different natural products of this class that are interesting for industrial purposes because of their odor qualities, i.e., of the enantiomeric form of 3-hydroxy-p-menthan-9-oic acid lactone 1, of mintlactone 2, of the 3,9-epoxy-p-menth-1,8(10)-diene 10, and of the pheromone vesperal 11 (Schemes 2 and 3).

  DOI：

  10.1002/1522-2675(200208)85:8<2489::aid-hlca2489>3.0.co;2-9

文献信息

• Naturalp-Menthene Monoterpenes: Synthesis of the Enantiomeric Forms of Wine Lactone, Epi-wine Lactone, Dill Ether, and Epi-dill Ether Starting from a Common Intermediate
  作者：Stefano Serra、Claudio Fuganti

  DOI：10.1002/hlca.200490189

  日期：2004.8

  A concise synthesis of the enantiomeric forms of wine lactone (5), epi-wine lactone (14), dill ether (6), and epi-dill ether (15) was accomplished starting from the enantiomeric forms of p-mentha-1,8(10)-diene-3,9-diol (8) (Scheme 3). The latter compounds were previously prepared in high optical purity by means of lipase-mediated kinetic resolution, and they were the common building blocks for this

  从p -mentha-1的对映体形式开始，简明地合成了葡萄酒内酯（5），表酒内酯（14），莳萝醚（6）和表莳萝醚（15）的对映体形式， 8（10）-二烯-3,9-二醇（8）（方案3）。后者化合物以前是通过脂肪酶介导的动力学拆分以高光学纯度制备的，它们是这种发散性合成的常见组成部分。关键步骤是许多化学和非对映选择性反应，其中8被氧化为内酯7（见表1）。），全面研究了7对内酯14和5（见表2）的非对映选择性还原，和烯醇醚16对醚15的还原。这种新的合成方法的有效性使得可以以高收率和几个简单的实验步骤制备标题对-薄荷烷单萜，这是香料工业相当感兴趣的。
• Boyer, Francois-Didier; Malosse, Christian; Zagatti, Pierre, Bulletin de la Societe Chimique de France, 1997, vol. 134, # 8-9, p. 757 - 764
  作者：Boyer, Francois-Didier、Malosse, Christian、Zagatti, Pierre、Einhorn, Jacques

  DOI：——

  日期：——