(3S,5E)-6-iodo-3,5-dimethyl-5-hexen-1-ol | 214260-98-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (3S,5E)-6-iodo-3,5-dimethyl-5-hexen-1-ol
• 英文别名: (E,3S)-6-iodo-3,5-dimethylhex-5-en-1-ol
• CAS: 214260-98-7
• 化学式: C₈H₁₅IO
• 分子量: 254.111
• InChiKey: IVKIMOIKWRBHAL-UQBZRGDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S,5E)-6-iodo-3,5-dimethyl-5-hexen-1-ol 在 碘 、 三苯基膦 作用下， 生成 (6R,8E)-6,8-dimethyl-9-iodo-8-nonenal
  参考文献：
  名称：

  Oxazoline N-Oxide-Mediated [2 + 3] Cycloadditions: Application to a Total Synthesis of the Hypocholesterolemic Agent 1233A

  摘要：

  Oxetanone 1233A1 has been synthesized in 22 steps and 3.43% overall yield from 3-methylglutaric anhydride. Asymmetric carbon at C-7 was introduced by a diastereoselective esterification of 3-methylglutaric anhydride, whereas the two asymmetric carbons at C-2' and C-3' were controlled by an asymmetric [2 +/- 3] cycloaddition using camphor-derived oxazoline N-oxide as dipole.

  DOI：

  10.1021/jo980813u
• 作为产物：
  描述：

  (3R,1'R)-5-hydroxy-3-methylpentanoic acid (1'-α-naphthyl)ethyl ester 在 二氯二茂锆 、 camphor-10-sulfonic acid 、 碘 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 63.5h， 生成 (3S,5E)-6-iodo-3,5-dimethyl-5-hexen-1-ol
  参考文献：
  名称：

  Oxazoline N-Oxide-Mediated [2 + 3] Cycloadditions: Application to a Total Synthesis of the Hypocholesterolemic Agent 1233A

  摘要：

  Oxetanone 1233A1 has been synthesized in 22 steps and 3.43% overall yield from 3-methylglutaric anhydride. Asymmetric carbon at C-7 was introduced by a diastereoselective esterification of 3-methylglutaric anhydride, whereas the two asymmetric carbons at C-2' and C-3' were controlled by an asymmetric [2 +/- 3] cycloaddition using camphor-derived oxazoline N-oxide as dipole.

  DOI：

  10.1021/jo980813u