(1S,2S,4R)-p-menthane-1,2,4-triol | 465529-97-9

• 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: (1S,2S,4R)-p-menthane-1,2,4-triol
• 英文别名: (1S,2S,4S)-trihydroxy-p-menthane；(1S,2S,4R)-1-Methyl-4-(1-methylethyl)-1,2,4-cyclohexanetriol；(1S,2S,4R)-1-methyl-4-propan-2-ylcyclohexane-1,2,4-triol
• CAS: 465529-97-9
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: RKROZYQLIWCOBD-LPEHRKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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：

  Toluene-4-sulfonic acid (R)-1-isopropyl-4-methyl-cyclohex-3-enyl ester 在 vanadia 双氧水 作用下， 以 丙酮 为溶剂， 生成 1(R),2(S),4(R)-Trihydroxy-p-menthan 、 (1S,2S,4R)-p-menthane-1,2,4-triol
  参考文献：
  名称：

  Stereoselective trans-dihydroxylation of terpinen-4-ol: synthesis of some stereoisomers of p-menthane-1,2,4-triol

  摘要：

  A high level of trans-stereoselectivity in the dihydroxylation of the homoallylic alcohol, terpinen-4-ol 1 (R=H) has been achieved. Thus, the enantiomeric triols 2a and 2b were separately synthesized in high yield and with high stereoselectivity by trans-dihydroxylation of the enantiomeric (4S)-terpinen-4-ol 1a (R = H), and (4R)-terpinen-4-ol 1b (R=H), respectively, using hydrogen peroxide as oxidant and V2O5; as catalyst. In the same way, the enantiomeric triols 3a and 3b were obtained from the enantiomeric (4S)-terpinen-4-yl tosylate 1a (R=tosyl) and (4R)-terpinen-4-yl tosylate 1b (R=tosyl), respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00207-0

文献信息

• Stereoselective trans-dihydroxylation of terpinen-4-ol: synthesis of some stereoisomers of p-menthane-1,2,4-triol
  作者：Ioan Cristea、Erika Kozma、Carmen Batiu

  DOI：10.1016/s0957-4166(02)00207-0

  日期：2002.6

  A high level of trans-stereoselectivity in the dihydroxylation of the homoallylic alcohol, terpinen-4-ol 1 (R=H) has been achieved. Thus, the enantiomeric triols 2a and 2b were separately synthesized in high yield and with high stereoselectivity by trans-dihydroxylation of the enantiomeric (4S)-terpinen-4-ol 1a (R = H), and (4R)-terpinen-4-ol 1b (R=H), respectively, using hydrogen peroxide as oxidant and V2O5; as catalyst. In the same way, the enantiomeric triols 3a and 3b were obtained from the enantiomeric (4S)-terpinen-4-yl tosylate 1a (R=tosyl) and (4R)-terpinen-4-yl tosylate 1b (R=tosyl), respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.