5-isopropenyl-2-methylcyclohex-2-enylmethanol | 5962-49-2

• 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: 5-isopropenyl-2-methylcyclohex-2-enylmethanol
• 英文别名: (2-Methyl-5-prop-1-en-2-ylcyclohex-2-en-1-yl)methanol
• CAS: 5962-49-2
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: ROXWNAVVBBPBPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  106 °C(Press: 5 Torr)
• 密度：
  0.9528 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  7-isopropenyl-4-methyl-1-oxa-spiro[2.5]oct-4-ene 在 zeolite (H-ZSM 5) 、 sodium cyanoborohydride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以59%的产率得到5-isopropenyl-2-methylcyclohex-2-enylmethanol
  参考文献：
  名称：

  沸石（H-ZSM 5）用氰基硼氢化钠催化2,3-环氧醇还原为1,2-二醇和乙烯基环氧化物的区域选择性立体异构化

  摘要：

  在回流二氯乙烷中，用沸石H-ZSM 5 / NaCNBH 3组合试剂体系，将各种2,3-环氧醇和乙烯基环氧化合物（在末端位置具有环氧部分）还原，得到1,2-二醇和均丙醇中等至良好的产量。在这些条件下，不影响酸敏感性基团如缩醛和THP醚，这表明反应条件温和。

  DOI：

  10.1016/s0040-4039(98)02610-0

文献信息

• Formaldehyde Encapsulated in Zeolite:  A Long-Lived, Highly Activated One-Carbon Electrophile to Carbonyl-Ene Reactions
  作者：Takahiro Okachi、Makoto Onaka

  DOI：10.1021/ja039737p

  日期：2004.3.3

  Gaseous formaldehyde is extremely unstable and readily undergoes self-polymerization to a solid paraformaldehyde or disproportionation to methanol and formic acid in the presence of moisture. We disclose a simple method to stably store such a labile formaldehyde as a monomer in a nanoporous faujasite zeolite at 5 degrees C for at least 50 days without self-polymerization or disproportionation. The greater stability of formaldehyde encapsulated in zeolite was confirmed by 13C MAS NMR spectroscopy. Formaldehyde was not only stabilized within the zeolite cages but functioned as a powerful electrophile toward various olefins. Zeolite-encapsulated formaldehyde was proved to be a stable but highly reactive C1 reagent.
• Zeolite (H-ZSM 5) catalysed regio and stereoselective reduction of 2,3-epoxy alcohols to 1,2-diols and vinylic epoxides to homoallylic alcohols with sodium cyanoborohydride
  作者：Anuradha Gupta、Yashwant D. Vankar

  DOI：10.1016/s0040-4039(98)02610-0

  日期：1999.2

  positions) undergo reduction with zeolite H-ZSM 5/NaCNBH3 combination of reagent system in refluxing dichloroethane to give 1,2-diols and homoallylic alcohols in moderate to good yields. Under these conditions acid sensitive groups such as an acetal and a THP ether are not affected which indicates the mildness of the reaction conditions.

  在回流二氯乙烷中，用沸石H-ZSM 5 / NaCNBH 3组合试剂体系，将各种2,3-环氧醇和乙烯基环氧化合物（在末端位置具有环氧部分）还原，得到1,2-二醇和均丙醇中等至良好的产量。在这些条件下，不影响酸敏感性基团如缩醛和THP醚，这表明反应条件温和。