(4R,6R,7S)-7-methyldec-1-en-9-yne-4,6-diol | 507480-27-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,6R,7S)-7-methyldec-1-en-9-yne-4,6-diol
• CAS: 507480-27-5
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: UWPXQCJIKISZES-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 (4R,6R,7S)-7-methyldec-1-en-9-yne-4,6-diol 在 4-甲基苯磺酸吡啶 作用下， 以 丙酮 为溶剂， 反应 15.0h， 以65%的产率得到(4R,6R)-4-allyl-2,2-dimethyl-6-[(1S)-1-methylbut-3-ynyl]-1,3-dioxane
  参考文献：
  名称：

  Formal Total Synthesis of Salicylihalamides A and B

  摘要：

  An efficient synthesis of the macrolactone 3 of the salicylihalamides in 10 linear steps from alkene 6 is described. The key steps involved a Stille coupling between the chiral stannane 5 and benzyl bromide 4, which produced alkene 15 in good yield, and subsequent base-induced macrolactonization then gave compound 3. Macrolactone 3 was then converted into the known salicylihalamide A intermediate 18 in a three-step sequence. Compound 3 was also converted into another known salicylihalamide A and B intermediate 23 in a five-step sequence.

  DOI：

  10.1021/jo026798h
• 作为产物：
  描述：

  在 吡啶 、 盐酸 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 18.33h， 生成 (4R,6R,7S)-7-methyldec-1-en-9-yne-4,6-diol
  参考文献：
  名称：

  Formal Total Synthesis of Salicylihalamides A and B

  摘要：

  An efficient synthesis of the macrolactone 3 of the salicylihalamides in 10 linear steps from alkene 6 is described. The key steps involved a Stille coupling between the chiral stannane 5 and benzyl bromide 4, which produced alkene 15 in good yield, and subsequent base-induced macrolactonization then gave compound 3. Macrolactone 3 was then converted into the known salicylihalamide A intermediate 18 in a three-step sequence. Compound 3 was also converted into another known salicylihalamide A and B intermediate 23 in a five-step sequence.

  DOI：

  10.1021/jo026798h