methyl (5R,7R)-5,7-dihydroxydodecanoate | 503310-35-8

• 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: methyl (5R,7R)-5,7-dihydroxydodecanoate
• CAS: 503310-35-8
• 化学式: C₁₃H₂₆O₄
• 分子量: 246.347
• InChiKey: GPBLYCNLWHEIQX-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (5R,7R)-5,7-dihydroxydodecanoate 在 对甲苯磺酸 、 N,N'-硫羰基二咪唑 、 三苯基膦 、 苯甲酸 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 168116.5h， 生成 (R)-6-庚基四氢吡喃-2-酮
  参考文献：
  名称：

  Absolute Configuration and Synthesis of β- and δ-Lactones Present in the Pheromone System of the Giant White Butterfly Idea leuconoe

  摘要：

  Males of the giant white butterfly Idea leuconoe release a complex mixture of compounds during courtship. Besides alkaloids, aromatics, terpenoids and hydrocarbons, several lactones have been identified in the pheromone bouquet. Two simple stereoselective methods to create the lactones in good enantiomeric excesses have been developed. The generation of the stereocenters of the beta-lactones 1a and 1b is based on a controlled C-C coupling by a Horner-Wadsworth-Emmons approach, followed by asymmetric dihydroxylation, whereas the synthesis of the delta-lactone 3b uses an enantioselective hydrogenation of a dioxoalkanoate precursor. The absolute configurations of the natural lactones 1a, 1b and 3b were determined by gas chromatography on a chiral stationary phase. Both 1a and 1b are of (S,S) configuration, suggesting their biosynthetic origin from (-)-viridifloric acid (7a) or (-)norviridifloric acid (7b), respectively. In contrast, natural 3b is a mixture of all enantiomers, in which the (5S,7S) enantiomer dominates.

  DOI：

  10.1002/1099-0690(200211)2002:22<3884::aid-ejoc3884>3.0.co;2-4
• 作为产物：
  描述：

  methyl 5,7-dioxododecanoate 在 (R)-Ru-BINAP 氢气 作用下， 以 甲醇 为溶剂， 80.0 ℃ 、4.0 MPa 条件下， 反应 120.0h， 以60%的产率得到methyl (5R,7R)-5,7-dihydroxydodecanoate
  参考文献：
  名称：

  Absolute Configuration and Synthesis of β- and δ-Lactones Present in the Pheromone System of the Giant White Butterfly Idea leuconoe

  摘要：

  Males of the giant white butterfly Idea leuconoe release a complex mixture of compounds during courtship. Besides alkaloids, aromatics, terpenoids and hydrocarbons, several lactones have been identified in the pheromone bouquet. Two simple stereoselective methods to create the lactones in good enantiomeric excesses have been developed. The generation of the stereocenters of the beta-lactones 1a and 1b is based on a controlled C-C coupling by a Horner-Wadsworth-Emmons approach, followed by asymmetric dihydroxylation, whereas the synthesis of the delta-lactone 3b uses an enantioselective hydrogenation of a dioxoalkanoate precursor. The absolute configurations of the natural lactones 1a, 1b and 3b were determined by gas chromatography on a chiral stationary phase. Both 1a and 1b are of (S,S) configuration, suggesting their biosynthetic origin from (-)-viridifloric acid (7a) or (-)norviridifloric acid (7b), respectively. In contrast, natural 3b is a mixture of all enantiomers, in which the (5S,7S) enantiomer dominates.

  DOI：

  10.1002/1099-0690(200211)2002:22<3884::aid-ejoc3884>3.0.co;2-4

文献信息

• Absolute Configuration and Synthesis of β- and δ-Lactones Present in the Pheromone System of the Giant White Butterfly Idea leuconoe
  作者：Katja Stritzke、Stefan Schulz、Ritsuo Nishida

  DOI：10.1002/1099-0690(200211)2002:22<3884::aid-ejoc3884>3.0.co;2-4

  日期：2002.11

  Males of the giant white butterfly Idea leuconoe release a complex mixture of compounds during courtship. Besides alkaloids, aromatics, terpenoids and hydrocarbons, several lactones have been identified in the pheromone bouquet. Two simple stereoselective methods to create the lactones in good enantiomeric excesses have been developed. The generation of the stereocenters of the beta-lactones 1a and 1b is based on a controlled C-C coupling by a Horner-Wadsworth-Emmons approach, followed by asymmetric dihydroxylation, whereas the synthesis of the delta-lactone 3b uses an enantioselective hydrogenation of a dioxoalkanoate precursor. The absolute configurations of the natural lactones 1a, 1b and 3b were determined by gas chromatography on a chiral stationary phase. Both 1a and 1b are of (S,S) configuration, suggesting their biosynthetic origin from (-)-viridifloric acid (7a) or (-)norviridifloric acid (7b), respectively. In contrast, natural 3b is a mixture of all enantiomers, in which the (5S,7S) enantiomer dominates.