(-)-(3R,5S)-3-hydroxy-5-decanolide | 135415-55-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (-)-(3R,5S)-3-hydroxy-5-decanolide
• 英文别名: (4R,6S)-4-hydroxy-6-pentyloxan-2-one
• CAS: 135415-55-3
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: WPOYJLMQCBFDQM-BDAKNGLRSA-N

物化性质

• 沸点：
  330.4±25.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (-)-(3R,5S)-3-hydroxy-5-decanolide 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 5.0h， 以70%的产率得到(6S)-6-pentyl-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Secondary metabolites by chemical screening -13. Enantioselective synthesis of δ-lactones from streptenola, achiral building block from streptomyces

  摘要：

  The enantioselective synthesis of all four stereoisomers of the secondary metabolite 3-hydroxy-5-decanolide (4a) from Cephalosporium recifei and both enantiomers of massoialactone (5a) by starting from one chiral building block, streptenol A (1a), a secondary metabolite from Streptomyces sp., is described. The key steps of the reaction sequence involve diastereoselective reduction of 1a to syn- or anti-triol 2a and 2b and the regioselective oxidation of the primary hydroxyl group. This reaction furnishes in one step the sigma-lactones 3a and 3b and requires no protecting group.

  DOI：

  10.1016/s0040-4020(01)86398-5
• 作为产物：
  描述：

  (3S,8E)-1,3-二羟基-8-癸烯-5-酮 在 palladium on activated charcoal sodium tetrahydroborate 、 tris(triphenylphosphine)ruthenium(II) chloride 、 氢气 、 溶剂黄146 作用下， 以 乙酸乙酯 、 苯 为溶剂， -70.0~25.0 ℃ 、101.33 kPa 条件下， 反应 83.0h， 生成 (-)-(3R,5S)-3-hydroxy-5-decanolide
  参考文献：
  名称：

  Secondary metabolites by chemical screening -13. Enantioselective synthesis of δ-lactones from streptenola, achiral building block from streptomyces

  摘要：

  The enantioselective synthesis of all four stereoisomers of the secondary metabolite 3-hydroxy-5-decanolide (4a) from Cephalosporium recifei and both enantiomers of massoialactone (5a) by starting from one chiral building block, streptenol A (1a), a secondary metabolite from Streptomyces sp., is described. The key steps of the reaction sequence involve diastereoselective reduction of 1a to syn- or anti-triol 2a and 2b and the regioselective oxidation of the primary hydroxyl group. This reaction furnishes in one step the sigma-lactones 3a and 3b and requires no protecting group.

  DOI：

  10.1016/s0040-4020(01)86398-5

文献信息

• Process for the stereoselective preparation of 5-substituted
  申请人：Hoechst Aktiengesellschaft

  公开号：US05292898A1

  公开（公告）日：1994-03-08

  A process for the stereoselective preparation of 5-substituted .delta.-lactones of the formulae Ia, Ib, Ic and Id ##STR1## in which R.sup.1 is a straight-chain or branched alkyl or alkenyl group or methylhydroxy, novel 5-substituted .delta.-lactones and novel intermediates, and use thereof as pharmaceuticals having cholesterol synthesis-inhibiting action, fragrances and flavorings is described.

  本发明涉及一种立体选择性制备式Ia、Ib、Ic和Id的5-取代.delta.-内酯的方法，其中R.sup.1是直链或支链烷基或烯基或甲基羟基，新颖的5-取代.delta.-内酯和新颖的中间体，以及作为具有抑制胆固醇合成作用的药物、香料和调味剂的用途。
• Verfahren zur stereoselektiven Herstellung von 5-substituierten delta-Lactonen und deren Verwendung
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0469480A2

  公开（公告）日：1992-02-05

  Es wird ein Verfahren zur stereoselektiven Herstellung von 5-substituierten 8-Lactonen der Formeln Ia, Ib, Ic und Id wobei R1 für geradkettige oder verzweigte Alkyl- oder Alkenylgruppe oder für Methylhydroxy steht, neue 5-substituierte δ-Lactone und neue Zwischenprodukte, sowie deren Verwendung als Arzneimittel mit Cholesterin-Synthese hemmender Wirkung, Duft- und Geschmackstoffe, beschrieben.

  一种立体选择性制备式 Ia、Ib、Ic 和 Id 的 5-取代 8-内酯的工艺 式中 R1 为直链或支链烷基或烯基或甲基羟基的新 5-取代的 δ-内酯和新中间体，以及它们作为具有胆固醇合成抑制活性的药物、香料和香精的用途。
• Secondary metabolites by chemical screening -13. Enantioselective synthesis of δ-lactones from streptenola, achiral building block from streptomyces
  作者：Yvonne Romeyke、Martin Keller、Heinz Kluge、Susanne Grabley、Peter Hammann

  DOI：10.1016/s0040-4020(01)86398-5

  日期：1991.1

  The enantioselective synthesis of all four stereoisomers of the secondary metabolite 3-hydroxy-5-decanolide (4a) from Cephalosporium recifei and both enantiomers of massoialactone (5a) by starting from one chiral building block, streptenol A (1a), a secondary metabolite from Streptomyces sp., is described. The key steps of the reaction sequence involve diastereoselective reduction of 1a to syn- or anti-triol 2a and 2b and the regioselective oxidation of the primary hydroxyl group. This reaction furnishes in one step the sigma-lactones 3a and 3b and requires no protecting group.