methyl (5R,7R)-5,7-dihydroxyoctanoate | 503310-40-5

• 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-dihydroxyoctanoate
• CAS: 503310-40-5
• 化学式: C₉H₁₈O₄
• 分子量: 190.24
• InChiKey: DVTCUIAUYLJAHZ-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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-dihydroxyoctanoate 在 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 72.0h， 以87%的产率得到(5R,7R)-7-hydroxy-5-octanolide
  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：

  4-氯甲酰基丁酸甲酯 在 (R)-Ru-BINAP 氢气 、 magnesium ethylate 、 二甲基亚砜 、 sodium chloride 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 80.0 ℃ 、4.0 MPa 条件下， 反应 128.0h， 生成 methyl (5R,7R)-5,7-dihydroxyoctanoate
  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

• The Vinylogous Aldol Reaction of Unsaturated Esters and Enolizable Aldehydes Using the Novel Lewis Acid Aluminum Tris(2,6-di-2-naphthylphenoxide)
  作者：Jeffrey A. Gazaille、Tarek Sammakia

  DOI：10.1021/ol300738f

  日期：2012.6.1

  (ATNP), and its use in the vinylogous aldol reaction between methyl crotonate and enolizable aldehydes are described. ATNP is related to Yamamoto’s Lewis acid, aluminum tris(2,6-diphenylphenoxide) (ATPH), but the 2-naphthyl groups more effectively block the α-position of aldehydes, enabling the selective enolization of crotonate esters in the presence of enolizable aldehydes. Vinylogous aldol reactions

  描述了新型路易斯酸、三(2,6-二-2-萘基苯氧基铝) (ATNP) 的合成及其在巴豆酸甲酯和烯醇化醛之间的乙烯醇醛反应中的用途。ATNP 与 Yamamoto 的路易斯酸、三(2,6-二苯酚铝) (ATPH) 有关，但 2-萘基更有效地阻断醛的 α 位，从而在可烯醇化醛的存在下实现巴豆酸酯的选择性烯醇化. 然后，使用各种底物，乙烯基羟醛反应可以顺利进行并以高产率进行。
• 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.