2-[(4s,6r)-2,2-Dimethyl-6-pentyl-1,3-dioxan-4-yl]ethanol | 1152531-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(4s,6r)-2,2-Dimethyl-6-pentyl-1,3-dioxan-4-yl]ethanol
• CAS: 1152531-76-4
• 化学式: C₁₃H₂₆O₃
• 分子量: 230.348
• InChiKey: ZYFFGFPHQHORGD-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  2-[(4s,6r)-2,2-Dimethyl-6-pentyl-1,3-dioxan-4-yl]ethanol 在 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 、 二氯甲烷 为溶剂， 反应 15.5h， 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：

  methyl (3R,5R)-3,5-dihydroxydecanoate 在 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 14.0h， 生成 2-[(4s,6r)-2,2-Dimethyl-6-pentyl-1,3-dioxan-4-yl]ethanol
  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

• Total synthesis of verbalactone: an efficient, carbohydrate-based approach
  作者：Ganesh B. Salunke、I. Shivakumar、Mukund K. Gurjar

  DOI：10.1016/j.tetlet.2009.02.062

  日期：2009.5

  A carbohydrate-based strategy for the total synthesis of verbalactone has been described. (3R,5R)-3,5-dihydroxydecanoic acid was dimerised under Yamaguchi conditions to provide verbalactone in an overall yield of 17% starting from 3-deoxy-1,2:5,6-di-O-isopropylidine-alpha-D-glucofuranose. (c) 2009 Elsevier Ltd. All rights reserved.