ethyl 2-[(4R,6R)-2,2-dimethyl-6-pentyl-1,3-dioxan-4-yl]acetate | 1073442-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-[(4R,6R)-2,2-dimethyl-6-pentyl-1,3-dioxan-4-yl]acetate
• CAS: 1073442-18-8
• 化学式: C₁₅H₂₈O₄
• 分子量: 272.385
• InChiKey: PXYLGNFVECTYFH-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 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 2-[(4R,6R)-2,2-dimethyl-6-pentyl-1,3-dioxan-4-yl]acetate 在 lithium aluminium tetrahydride 、 重铬酸吡啶 、 potassium tert-butylate 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 (4S,6R)-undec-1-ene-4,6-diol
  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：

  ethyl (3R,5R)-3,5-dihydroxydecanoate 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以85%的产率得到ethyl 2-[(4R,6R)-2,2-dimethyl-6-pentyl-1,3-dioxan-4-yl]acetate
  参考文献：
  名称：

  Synthesis of (+)-(3R,5R)-3-Hydroxy-5-decanolide and Massoialactone, and Formal Synthesis of Verbalactone

  摘要：

  Total synthesis of (3R, 5R)-(+)-3-hydroxy-5-decanolide (1) and massoialactone (2), and formal synthesis of verbalactone (3), have been reported.

  DOI：

  10.1080/00397910802055294

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.
• Synthesis of (+)-(3<i>R</i>,5<i>R</i>)-3-Hydroxy-5-decanolide and Massoialactone, and Formal Synthesis of Verbalactone
  作者：Gowravaram Sabitha、V. Bhaskar、J. S. Yadav

  DOI：10.1080/00397910802055294

  日期：2008.8.29

  Total synthesis of (3R, 5R)-(+)-3-hydroxy-5-decanolide (1) and massoialactone (2), and formal synthesis of verbalactone (3), have been reported.