2-(iodomethyl)-4-hydroxy-4-methyltetrahydropyran | 134360-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-(iodomethyl)-4-hydroxy-4-methyltetrahydropyran
• 英文别名: 2-(Iodomethyl)-4-methyloxan-4-ol
• CAS: 134360-80-8
• 化学式: C₇H₁₃IO₂
• 分子量: 256.084
• InChiKey: BYVXJNITQUNEGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(iodomethyl)-4-hydroxy-4-methyltetrahydropyran 在 1,5-二氮杂双环[4.3.0]壬-5-烯 作用下， 反应 10.0h， 以100%的产率得到4-Methyl-2-methylene-tetrahydro-pyran-4-ol
  参考文献：
  名称：

  Synthesis of (S)-(+)-mevalonolactone and mevalonate analogs

  摘要：

  Tetrahydropyran (R/S)-1, a vinylidene analogue of mevalonolactone, was prepared by addition of excess allyl Grignard to 4-acetoxy-2-butanone, iodoetherification of the resultant diol 5, and DBN-mediated dehydrohalogenation. Sharpless asymmetric epoxidation of 3-methylhexa-2,5-dien-1-ol (9) gave epoxide 10 that was reduced to diol 11 (> 95% ee) by LiA1H4. Annulation and elimination of HI as described for 5 furnished (S)-1. Ozonolysis of (S)-1 yielded (S)-mevalonolactone (2), whereas bromomethoxylation and controlled hydrolysis led to 3, a reactive analogue of (S)-mevalonic acid. Analogue 4, a nonionizable lipophilic version of (S)-mevalonic acid, was generated upon exposure of (S)-1 or 2 to excess Tebbe-Grubbs reagent.

  DOI：

  10.1021/jo00013a030
• 作为产物：
  描述：

  (R/S)-3-methyl-5-hexene-1,3-diol 在 碘 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以70%的产率得到2-(iodomethyl)-4-hydroxy-4-methyltetrahydropyran
  参考文献：
  名称：

  Synthesis of (S)-(+)-mevalonolactone and mevalonate analogs

  摘要：

  Tetrahydropyran (R/S)-1, a vinylidene analogue of mevalonolactone, was prepared by addition of excess allyl Grignard to 4-acetoxy-2-butanone, iodoetherification of the resultant diol 5, and DBN-mediated dehydrohalogenation. Sharpless asymmetric epoxidation of 3-methylhexa-2,5-dien-1-ol (9) gave epoxide 10 that was reduced to diol 11 (> 95% ee) by LiA1H4. Annulation and elimination of HI as described for 5 furnished (S)-1. Ozonolysis of (S)-1 yielded (S)-mevalonolactone (2), whereas bromomethoxylation and controlled hydrolysis led to 3, a reactive analogue of (S)-mevalonic acid. Analogue 4, a nonionizable lipophilic version of (S)-mevalonic acid, was generated upon exposure of (S)-1 or 2 to excess Tebbe-Grubbs reagent.

  DOI：

  10.1021/jo00013a030

文献信息

• BOLITT, VERONIQUE;MIOSKOWSKI, CHARLES;BHATT, R. K.;FALCK, J. R., J. ORG. CHEM., 56,(1991) N3, C. 4238-4240
  作者：BOLITT, VERONIQUE、MIOSKOWSKI, CHARLES、BHATT, R. K.、FALCK, J. R.

  DOI：——

  日期：——