(+)-(3S,5R,8E)-3-hydroxy-5-dec-8-enolide | 135352-06-6

• 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: (+)-(3S,5R,8E)-3-hydroxy-5-dec-8-enolide
• 英文别名: (4S,6R)-4-hydroxy-6-[(E)-pent-3-enyl]oxan-2-one
• CAS: 135352-06-6
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: BRYQUZBMBRPZDJ-AHQHDXANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (+)-(3S,5R,8E)-3-hydroxy-5-dec-8-enolide 以185 mg (92%)的产率得到(+)-(3S,5R)-3-hydroxy-5-decanolide
  参考文献：
  名称：

  Process for the stereoselective preparation of 5-substituted

  摘要：

  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。

  公开号：

  US05292898A1
• 作为产物：
  描述：

  (3S,8E)-1,3-二羟基-8-癸烯-5-酮 在 sodium tetrahydroborate 、 tris(triphenylphosphine)ruthenium(II) chloride 、 (C₃H₇)4NRuO₄ 、 三氯化铁 、 L-Selectride 、 溶剂黄146 、 N-甲基吗啉氧化物 、 lithium bromide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 异丙醇 、 苯 为溶剂， 反应 88.75h， 生成 (+)-(3S,5R,8E)-3-hydroxy-5-dec-8-enolide
  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。
• 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.