(2E,4Z)-2-methyldodeca-2,4-dienoic acid | 1093838-61-9

• 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: (2E,4Z)-2-methyldodeca-2,4-dienoic acid
• 英文别名: 2-methyl-dodeca-(2E,4Z)-dienoic acid
• CAS: 1093838-61-9
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: RNPDCAAZAYHCFV-XAZJVICWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4Z)-2-methyldodeca-2,4-dienoic acid 在 lithium hydroxide monohydrate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 16.75h， 生成 3-methoxy-2-[2-(2-methyl-dodeca-2,4-dienoylamino)-propionylamino]-acrylic acid methyl ester
  参考文献：
  名称：

  Synthesis and evaluation of structural requirements for antifungal activity of cyrmenin B1 analogues

  摘要：

  In a study aiming to define the structural elements essential to cyrmenin B-1 antifungal activity, the synthesis of a series of analogues was carried out. The structural modification introduced stepwise in distinct areas of the parent molecule allowed a deeper insight to be gained into the most relevant structural features affecting the activity of the natural compound. The bioassay results clearly indicate the relevance of each portion of the parent molecule, only the modification of the conjugated double bond geometry being tolerated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.023
• 作为产物：
  描述：

  (2E,4Z)-2-methyldodeca-2,4-dienoic acid methyl ester 在 lithium hydroxide monohydrate 、 水 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以90%的产率得到(2E,4Z)-2-methyldodeca-2,4-dienoic acid
  参考文献：
  名称：

  First Total Synthesis of Cyrmenin B₁

  摘要：

  A short and efficient synthesis of cyrmenin B-1, an antifungal metabolite of myxobacteria Cystobacter armeniaca and Archangium gephyra, is described. The crucial steps of the synthesis included the formation of the dehydroalanine moiety from the corresponding serine acetate and the formation of the beta-methoxyacrylate system via trimethylsilyldiazomethane methylation of the corresponding beta-hydroxy enamide.

  DOI：

  10.1021/jo802209m

文献信息

• ANTIOXIDANTS AND VEGETABLE OILS AS STABILIZERS OF INSECT SEMIOCHEMICALS
  申请人：Zhang Qing-He

  公开号：US20120270944A1

  公开（公告）日：2012-10-25

  Semiochemicals are combined with oils and/or antioxidants in order to control and maintain the necessary threshold release rates of the semiochemicals (such as attractants or repellents) from release devices for optimal activity/performance, for the reduction or elimination of semiochemical oxidation, isomerization, breakdown and polymerization, and also for stabilizing and/or protecting the active semiochemical ingredients.
• First Total Synthesis of Cyrmenin B₁
  作者：Narayan S. Chakor、Loana Musso、Sabrina Dallavalle

  DOI：10.1021/jo802209m

  日期：2009.1.16

  A short and efficient synthesis of cyrmenin B-1, an antifungal metabolite of myxobacteria Cystobacter armeniaca and Archangium gephyra, is described. The crucial steps of the synthesis included the formation of the dehydroalanine moiety from the corresponding serine acetate and the formation of the beta-methoxyacrylate system via trimethylsilyldiazomethane methylation of the corresponding beta-hydroxy enamide.
• Synthesis and evaluation of structural requirements for antifungal activity of cyrmenin B1 analogues
  作者：Narayan S. Chakor、Sabrina Dallavalle、Loana Musso、Paola Sardi

  DOI：10.1016/j.tetlet.2011.11.023

  日期：2012.1

  In a study aiming to define the structural elements essential to cyrmenin B-1 antifungal activity, the synthesis of a series of analogues was carried out. The structural modification introduced stepwise in distinct areas of the parent molecule allowed a deeper insight to be gained into the most relevant structural features affecting the activity of the natural compound. The bioassay results clearly indicate the relevance of each portion of the parent molecule, only the modification of the conjugated double bond geometry being tolerated. (C) 2011 Elsevier Ltd. All rights reserved.