(5R,7S)-7-hydroxy-5-dodecanolide | 121772-35-8

• 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: (5R,7S)-7-hydroxy-5-dodecanolide
• 英文别名: (5r,7s)-7-Hydroxy-5-dodecanolid；(6R)-6-[(2S)-2-hydroxyheptyl]oxan-2-one
• CAS: 121772-35-8
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: XLTJMMLYOQDLMD-WDEREUQCSA-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

• 作为产物：
  描述：

  (R)-6-((1R,2S)-1-Bromo-2-hydroxy-heptyl)-5,6-dihydro-pyran-2-one 在 镍 氢气 、 calcium carbonate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以71%的产率得到(5R,7S)-7-hydroxy-5-dodecanolide
  参考文献：
  名称：

  Signorella, Sandra R.; Cravero, Raquel M.; Sala, Luis F., Synthetic Communications, 1988, vol. 18, # 16-17, p. 1935 - 1946

  摘要：

  DOI：

文献信息

• Asymmetric synthesis of (+)-(S)-Massoia lactone, pheromone of Idea leuconoe. Formal total synthesis of valilactone and lachnelluloic acid
  作者：I. V. Mineeva

  DOI：10.1134/s1070428013110146

  日期：2013.11

  Simple and efficient asymmetric synthesis was developed of the cyclic scaffold of (-)-valilactone, an effective inhibitor of the pancreas lipase, applying the Keck allylation in the key stage of building up the carbon skeleton of the target molecule and of the unnatural (S)-isomer of Massoia lactone, lachnelluloic acid, possessing fungicidal properties, and (5R,7S)-7-hydroxy-5-dodecanolid, pheromone

  开发了一种简单有效的不对称合成方法，合成了一种有效的胰腺脂肪酶抑制剂（-）-半乳糖内酯的环状骨架，并在形成靶分子和非天然（S）碳骨架的关键阶段应用了Keck烯丙基化反应。）的异构体，具有杀真菌的特性，以及（5 R，7 S）-7-羟基-5-十二烷醇，大树若虫蝴蝶Idea leuconoe的信息素成分。
• 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.
• SIGNORELLA, SANDRA R.;CRAVERO, RAQUEL M.;SALA, LUIS F.;RUVEDA, EDMUNDO A., SYNTH. COMMUN., 18,(1988) N 16-17, C. 1935-1945
  作者：SIGNORELLA, SANDRA R.、CRAVERO, RAQUEL M.、SALA, LUIS F.、RUVEDA, EDMUNDO A.

  DOI：——

  日期：——
• Signorella, Sandra R.; Cravero, Raquel M.; Sala, Luis F., Synthetic Communications, 1988, vol. 18, # 16-17, p. 1935 - 1946
  作者：Signorella, Sandra R.、Cravero, Raquel M.、Sala, Luis F.、Ruveda, Edmundo A.

  DOI：——

  日期：——