ethyl (2E)-4-[(4S,6R)-2,2-dimethyl-6-pentyl-1,3-dioxan-4-yl]but-2-enoate | 1448062-01-8

• 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: ethyl (2E)-4-[(4S,6R)-2,2-dimethyl-6-pentyl-1,3-dioxan-4-yl]but-2-enoate
• 英文别名: Ethyl (2e)-4-[(4s,6r)-2,2-dimethyl-6-pentyl-1,3-dioxan-4-yl]but-2-enoate；ethyl (E)-4-[(4S,6R)-2,2-dimethyl-6-pentyl-1,3-dioxan-4-yl]but-2-enoate
• CAS: 1448062-01-8
• 化学式: C₁₇H₃₀O₄
• 分子量: 298.423
• InChiKey: IHHHBLAFAVEFDL-NZETUCKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2E)-4-[(4S,6R)-2,2-dimethyl-6-pentyl-1,3-dioxan-4-yl]but-2-enoate 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 、 硼酸 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 25.5h， 生成 (5S,7R)-7-hydroxy-5-dodecanolide
  参考文献：
  名称：

  Methyl (3R,5R)-3,5-dihydroxydecanoate in the asymmetric synthesis of Idea Leuconoe pheromone and formal syntheses of (+)-(3R,5R)-3-hydroxydecano-5-lactone, verbalactone, and Tolypothrix pentaether

  摘要：

  A simple and efficient asymmetric synthesis of (5S,7R)-7-hydroxydodecano-5-lactone, a component of the giant danaine butterfly Idea leuconoe pheromone, and formal syntheses of (+)-(3R,5R)-3-hydroxydecano-5-lactone, verbalactone, and Tolypothrix pentaether have been accomplished starting from methyl (3R,5R)-3,5-dihydroxydecanoate. The latter is obtained from methyl 3-[(tributylstannyl)methyl]but-3-enoate using Keck allylation in the key step of the construction of its carbon skeleton.

  DOI：

  10.1134/s1070428013060067
• 作为产物：
  描述：

  methyl (3R,5R)-3,5-dihydroxydecanoate 在 lithium aluminium tetrahydride 、 重铬酸吡啶 、 4-甲基苯磺酸吡啶 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 48.0h， 生成 ethyl (2E)-4-[(4S,6R)-2,2-dimethyl-6-pentyl-1,3-dioxan-4-yl]but-2-enoate
  参考文献：
  名称：

  Methyl (3R,5R)-3,5-dihydroxydecanoate in the asymmetric synthesis of Idea Leuconoe pheromone and formal syntheses of (+)-(3R,5R)-3-hydroxydecano-5-lactone, verbalactone, and Tolypothrix pentaether

  摘要：

  A simple and efficient asymmetric synthesis of (5S,7R)-7-hydroxydodecano-5-lactone, a component of the giant danaine butterfly Idea leuconoe pheromone, and formal syntheses of (+)-(3R,5R)-3-hydroxydecano-5-lactone, verbalactone, and Tolypothrix pentaether have been accomplished starting from methyl (3R,5R)-3,5-dihydroxydecanoate. The latter is obtained from methyl 3-[(tributylstannyl)methyl]but-3-enoate using Keck allylation in the key step of the construction of its carbon skeleton.

  DOI：

  10.1134/s1070428013060067

文献信息

• Methyl (3R,5R)-3,5-dihydroxydecanoate in the asymmetric synthesis of Idea Leuconoe pheromone and formal syntheses of (+)-(3R,5R)-3-hydroxydecano-5-lactone, verbalactone, and Tolypothrix pentaether
  作者：I. V. Mineeva

  DOI：10.1134/s1070428013060067

  日期：2013.6

  A simple and efficient asymmetric synthesis of (5S,7R)-7-hydroxydodecano-5-lactone, a component of the giant danaine butterfly Idea leuconoe pheromone, and formal syntheses of (+)-(3R,5R)-3-hydroxydecano-5-lactone, verbalactone, and Tolypothrix pentaether have been accomplished starting from methyl (3R,5R)-3,5-dihydroxydecanoate. The latter is obtained from methyl 3-[(tributylstannyl)methyl]but-3-enoate using Keck allylation in the key step of the construction of its carbon skeleton.