(3R)-3-hydroxyhex-5-ynoic acid | 1059625-56-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (3R)-3-hydroxyhex-5-ynoic acid
• CAS: 1059625-56-7
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: SZCONGVTALHNAO-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R)-3-hydroxyhex-5-ynoic acid 在 Lindlar's catalyst 喹啉 、 lithium hydroxide 、 copper(l) iodide 、 氢气 、 potassium carbonate 、 sodium iodide 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 9.0h， 生成 (3R,5Z,8Z,11Z,14Z)-3-hydroxyeicosa-5,8,11,14-tetraenoic acid
  参考文献：
  名称：

  A novel synthesis of 3(R)-HETE, 3(R)-HTDE and enzymatic synthesis of 3(R),15(S)-DiHETE

  摘要：

  3(R)-HETE and 3(R)-HTDE were prepared by cross-coupling of methyl 3(R)-hydroxyhex-5-ynoate either with 1-bromo-2,5,8-tetradecatriyne or 1-bromo-2-octyne followed by catalytic hydrogenation of the skipped triple bonds formed using Lindlar's catalyst. Enzymatic synthesis of 3(R),15(S)-DiHETE was accomplished by soybean LOX-1 using 3(R)-HETE as a substrate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01289-9
• 作为产物：
  描述：

  (3R)-3-hydroxy-5-hexynenitrile 在 sodium hydroxide 作用下， 反应 3.0h， 生成 (3R)-3-hydroxyhex-5-ynoic acid
  参考文献：
  名称：

  A novel synthesis of 3(R)-HETE, 3(R)-HTDE and enzymatic synthesis of 3(R),15(S)-DiHETE

  摘要：

  3(R)-HETE and 3(R)-HTDE were prepared by cross-coupling of methyl 3(R)-hydroxyhex-5-ynoate either with 1-bromo-2,5,8-tetradecatriyne or 1-bromo-2-octyne followed by catalytic hydrogenation of the skipped triple bonds formed using Lindlar's catalyst. Enzymatic synthesis of 3(R),15(S)-DiHETE was accomplished by soybean LOX-1 using 3(R)-HETE as a substrate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01289-9

文献信息

• [EN] METHOD FOR THE PRODUCTION OF R-HYDROXYCARBOXYLIC ACIDS<br/>[FR] PROCÉDÉ DE FABRICATION D'ACIDES R-HYDROXYCARBOXYLIQUES
  申请人：EMPA

  公开号：WO2008113190A1

  公开（公告）日：2008-09-25

  [EN] The present invention provides a method for production of enantiomerically pure R-hydroxycarboxylic acids by in vivo degradation of biopolymer polyhydroxyalkanoates (PHAs). The method comprises the steps of: 1) synthesizing PHAs by cultivating microorganisms in batch, fed-batch, or continuous cultures; 2) adjusting the pH of the culture to a level allowing the enzymatic depolymerization of said PHAs into one or more corresponding monomeric RHAs and the secretion of said RHAs into the culture medium; 3) incubating the culture at a set pH; 4) acidifying the pH of said culture and 5) optionally purifying the RHA monomers. The present process gives high product purity and yield, leads to effective cost reduction, easy downstream processing and environmentally friendly. Furthermore, the invention encompasses a plant for the production of R-hydroxycarboxylic acids (RHAs) by in vivo depolymerization of PHAs.
  [FR] La présente invention porte sur un procédé de production d'acides R-hydroxycarboxyliques énantiomériquement purs par dégradation in vivo de polyhydroxyalcanoates biopolymères (PHA). Le procédé comprend les étapes consistant à : 1) synthétiser des PHA par culture de micro-organismes dans des cultures par lots, semi-discontinues ou continues; 2) ajuster le pH de la culture à un niveau permettant la dépolymérisation enzymatique desdits PHA en un ou plusieurs RHA monomères correspondants et la sécrétion desdits RHA dans le milieu de culture; 3) faire incuber la culture à un pH défini; 4) acidifier le pH de ladite culture et 5) facultativement purifier les monomères RHA. Le présent procédé permet d'obtenir un produit de haute pureté et à haut rendement, une réduction des coûts effective, un traitement en aval aisé et est respectueux de l'environnement. De plus, l'invention porte sur une installation pour la production d'acides R-hydroxycarboxyliques (RHA) par dépolymérisation in vivo des PHA.
• A novel synthesis of 3(R)-HETE, 3(R)-HTDE and enzymatic synthesis of 3(R),15(S)-DiHETE
  作者：Natalia V Groza、Igor V Ivanov、Stepan G Romanov、Galina I Myagkova、Santosh Nigam

  DOI：10.1016/s0040-4020(02)01289-9

  日期：2002.12

  3(R)-HETE and 3(R)-HTDE were prepared by cross-coupling of methyl 3(R)-hydroxyhex-5-ynoate either with 1-bromo-2,5,8-tetradecatriyne or 1-bromo-2-octyne followed by catalytic hydrogenation of the skipped triple bonds formed using Lindlar's catalyst. Enzymatic synthesis of 3(R),15(S)-DiHETE was accomplished by soybean LOX-1 using 3(R)-HETE as a substrate. (C) 2002 Elsevier Science Ltd. All rights reserved.