(4R,6R,7S)-6-(4-Methoxy-benzyloxy)-7-methyl-dec-1-en-9-yn-4-ol | 507480-08-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4R,6R,7S)-6-(4-Methoxy-benzyloxy)-7-methyl-dec-1-en-9-yn-4-ol
• 英文别名: (4R,6R,7S)-6-[(4-methoxyphenyl)methoxy]-7-methyldec-1-en-9-yn-4-ol
• CAS: 507480-08-2
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: XDDNSCBRQPCWBU-KVSKMBFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,6R,7S)-6-(4-Methoxy-benzyloxy)-7-methyl-dec-1-en-9-yn-4-ol 在 盐酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 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
• 作为产物：
  描述：

  在 吡啶 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 16.33h， 生成 (4R,6R,7S)-6-(4-Methoxy-benzyloxy)-7-methyl-dec-1-en-9-yn-4-ol
  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