(5S,7S)-7-hydroxy-5-dodecanolide | 503310-38-1

• 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: (5S,7S)-7-hydroxy-5-dodecanolide
• 英文别名: (6S)-6-[(2S)-2-hydroxyheptyl]oxan-2-one
• CAS: 503310-38-1
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: XLTJMMLYOQDLMD-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S,7S)-7-hydroxy-5-dodecanolide 在 N,N'-硫羰基二咪唑 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 168004.5h， 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 (5R,7R)-5,7-dihydroxydodecanoate 在 对甲苯磺酸 、 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 112.0h， 生成 (5S,7S)-7-hydroxy-5-dodecanolide
  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

• 10.1021/acs.joc.4c00158
  作者：Dissanayake, Gihan C.、Martinez, James B.、Garg, Gaurav、Ndi, Cornelius、Markley, Jana L.、Hanson, Paul R.

  DOI：10.1021/acs.joc.4c00158

  日期：——

  A one-pot, sequential phosphate tether-mediated method for the synthesis of simplified 2-desmethyl sanctolide A analogs is reported. Western side-chain diversification was achieved using a pot-efficient, sequential cross metathesis (CM)/ring-closing metathesis (RCM)/H2/dephosphorylation procedure. Further diversification was achieved by Me3Al-mediated amide formation, Yamaguchi esterification, and

  报道了一种用于合成简化的 2-去甲基桑托内酯 A 类似物的一锅、连续磷酸盐系链介导的方法。使用高效、顺序交叉复分解(CM)/闭环复分解(RCM)/H 2 /去磷酸化程序实现了Western侧链多样化。通过 Me 3 Al 介导的酰胺形成、Yamaguchi 酯化和 RCM 大环化实现了进一步多样化，获得了稳定性得到改善的五种 C11/C12 Z构型 2-des-methyl sainttolide A 类似物。
• 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.