(2R,4R)-2-(4-methoxyphenyl)-4-[(2S)-pent-4-yn-2-yl]-1,3-dioxane | 507480-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,4R)-2-(4-methoxyphenyl)-4-[(2S)-pent-4-yn-2-yl]-1,3-dioxane
• CAS: 507480-06-0
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: CIMOVWKSPFZRJI-APHBMKBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4R)-2-(4-methoxyphenyl)-4-[(2S)-pent-4-yn-2-yl]-1,3-dioxane 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 为溶剂， 反应 1.33h， 生成 (4S,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
• 作为产物：
  描述：

  (2S)-2-[(4R)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]propan-1-ol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 30.0h， 生成 (2R,4R)-2-(4-methoxyphenyl)-4-[(2S)-pent-4-yn-2-yl]-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