(5Z)-8-hydroxyoctaenoic acid | 86982-56-1

• 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: (5Z)-8-hydroxyoctaenoic acid
• 英文别名: (z)-8-Hydroxyoct-5-enoic acid
• CAS: 86982-56-1
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: NMWHGTRTJQHXGY-IWQZZHSRSA-N

物化性质

• 沸点：
  319.5±30.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (5Z)-8-hydroxyoctaenoic acid 在 sodium azide 、 三氟化硼乙醚 、 水 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 Methyl 8-<(ethoxycarbonyl)amino>-(Z)-5-octenoate
  参考文献：
  名称：

  Enantioselective rhodium-mediated synthesis of (-)-PGE2 methyl ester

  摘要：

  Intramolecular Rh(II) carboxylate catalyzed cyclization of an alpha-diazo beta-methylene ketone to form a fused cyclopropane is shown to compete efficiently with beta-hydride elimination, so long as a catalyst derived from an electron-donating carboxylate is used. Cyclization of diazoketone 3 gives 2, which on opening with thiophenol followed by oxidative rearrangement gives PGE2 methyl ester 1. Prostaglandins having the 8-beta configuration, recently identified as being physiologically important, can also be prepared using this approach.

  DOI：

  10.1021/jo00028a012
• 作为产物：
  描述：

  methyl 8-hydroxy-5-octynoate 在 Pd-BaSO₄ sodium hydroxide 、 氢气 作用下， 生成 (5Z)-8-hydroxyoctaenoic acid
  参考文献：
  名称：

  Palladium-mediated transannular cyclizations of medium-ring olefinic enolsilanes

  摘要：

  Medium-ring olefinic ketone and lactone enolsilanes were subjected to palladium(II)-mediated cycloalkenylation conditions. Diverse bicyclic ring products were obtained in moderate to good yields. The effect of olefin geometry and ring size is discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.125

文献信息

• Dimethyleicosatrienoic acids: Inhibitors of the 5-lipoxygenase enzyme
  作者：Carl D. Perchonock、Joseph A. Finkelstein、Irene Uzinskas、John G. Gleason、Henry M. Sarau、Lenora B. Cieslinski

  DOI：10.1016/s0040-4039(00)81954-1

  日期：1983.1
• Hepoxilins and modulators of ichthyin for treatment skin disorders
  申请人：Fischer Judith

  公开号：US20070197639A1

  公开（公告）日：2007-08-23

  The present application relates to compositions and methods for treating skin disorders, dry skin, and protection of skin in inflammatory events. The present application more particularly discloses the identification of new genes and metabolic pathways involved in skin disorders, which provide novel targets and approaches for treating said disorders and for screening biologically active compounds. The present invention also provides various products and constructs, such as probes, primers, vectors, recombinant cells, which can be used to implement the above methods. The invention may be used to detect or treat various skin disorders, particularly dry and inflammatory skin disorders, in various subjects, including mammalian subjects, particularly human beings.
• [EN] UNSATURATED FATTY ACIDS AND THEIR USES IN THERAPY<br/>[FR] ACIDES GRAS INSATURES ET UTILISATIONS THERAPEUTIQUES
  申请人：COMMW SCIENT IND RES ORG

  公开号：WO2001046115A1

  公开（公告）日：2001-06-28

  This invention relates to a method for the treatment or prevention of coronary heart disease including the step of administering a polyunsaturated fatty acid or derivative thereof, said polyunsaturated fatty acid including: a linear chain of 18 carbon atoms, and two or more double bonds in the linear chain, wherein said polyunsaturated fatty acid is an n-1, n-2, n-3, n-4 or n-5 fatty acid, but excluding 183n-3 (Δ9,12,15) .
• Enantioselective rhodium-mediated synthesis of (-)-PGE2 methyl ester
  作者：Douglass F. Taber、R. Scott Hoerrner

  DOI：10.1021/jo00028a012

  日期：1992.1

  Intramolecular Rh(II) carboxylate catalyzed cyclization of an alpha-diazo beta-methylene ketone to form a fused cyclopropane is shown to compete efficiently with beta-hydride elimination, so long as a catalyst derived from an electron-donating carboxylate is used. Cyclization of diazoketone 3 gives 2, which on opening with thiophenol followed by oxidative rearrangement gives PGE2 methyl ester 1. Prostaglandins having the 8-beta configuration, recently identified as being physiologically important, can also be prepared using this approach.
• Palladium-mediated transannular cyclizations of medium-ring olefinic enolsilanes
  作者：Andrew S. Kende、Clara E. Mota Nelson、Sébastien Fuchs

  DOI：10.1016/j.tetlet.2005.09.125

  日期：2005.11

  Medium-ring olefinic ketone and lactone enolsilanes were subjected to palladium(II)-mediated cycloalkenylation conditions. Diverse bicyclic ring products were obtained in moderate to good yields. The effect of olefin geometry and ring size is discussed. (c) 2005 Elsevier Ltd. All rights reserved.