(4'S,9Z)-10-(2,2-dimethyl-1,3-dioxalan-4-yl)-dec-9-enoic acid methyl ester | 460077-82-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4'S,9Z)-10-(2,2-dimethyl-1,3-dioxalan-4-yl)-dec-9-enoic acid methyl ester
• 英文别名: methyl (Z)-10-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]dec-9-enoate
• CAS: 460077-82-1
• 化学式: C₁₆H₂₈O₄
• 分子量: 284.396
• InChiKey: VAMMSXHWDHBHGC-FPAJZGIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  (4'S,9Z)-10-(2,2-dimethyl-1,3-dioxalan-4-yl)-dec-9-enoic acid methyl ester 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成 (11S,9Z)-12-[(tert-butyldimethylsilyl)oxy]-11-hydroxydodec-9-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis of Mayolene-16 and Mayolene-18:  Larval Defensive Lipids from the European Cabbage Butterfly

  摘要：

  A tandem Wittig approach has been employed for the synthesis of both (11S,9Z,l2Z,15Z)- and (11R,9Z,12Z,15Z)-hydroxyoctadeca-9,12,15-trienoic acid (11-hydroxylinolenic acid, 11-HLA) from (R)-glyceraldehyde acetonide. From (11R)-HIA we have prepared the corresponding palmitic acid and stearic acid esters, mayolene-16 (1) and mayolene-18 (2), insect defensive compounds recently identified from Pieris rapae larvae. In addition, we describe the synthesis of three macrocyclic oligomers (24-26) derived from (11R)-HLA.

  DOI：

  10.1021/jo011102q
• 作为产物：
  描述：

  (9-methoxy-9-oxononyl)triphenylphosphonium bromide 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 以66%的产率得到(4'S,9Z)-10-(2,2-dimethyl-1,3-dioxalan-4-yl)-dec-9-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis of Mayolene-16 and Mayolene-18:  Larval Defensive Lipids from the European Cabbage Butterfly

  摘要：

  A tandem Wittig approach has been employed for the synthesis of both (11S,9Z,l2Z,15Z)- and (11R,9Z,12Z,15Z)-hydroxyoctadeca-9,12,15-trienoic acid (11-hydroxylinolenic acid, 11-HLA) from (R)-glyceraldehyde acetonide. From (11R)-HIA we have prepared the corresponding palmitic acid and stearic acid esters, mayolene-16 (1) and mayolene-18 (2), insect defensive compounds recently identified from Pieris rapae larvae. In addition, we describe the synthesis of three macrocyclic oligomers (24-26) derived from (11R)-HLA.

  DOI：

  10.1021/jo011102q