(Z)-5-decenoic acid | 84168-28-5

• 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: (Z)-5-decenoic acid
• 英文别名: (Z)-dec-5-enoic acid
• CAS: 84168-28-5
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: UJUXUEKQHBXUEM-WAYWQWQTSA-N

物化性质

• 沸点：
  277.3±9.0 °C(Predicted)
• 密度：
  0.936±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (Z)-5-decenoic acid 在 氯化亚砜 作用下， 反应 4.0h， 生成 (Z)-5-Decenoyl chloride
  参考文献：
  名称：

  Inhibitory Effect of 2-(E-2-Alkenoylamino)ethyl Alkyl Sulfides on Gastric Ulceration in Rats. II. Structure and Activity Relationships of 2-(E-n or Z-n-Decenoylamino)ethyl Alkyl Sulfides.

  摘要：

  2-(E型或Z型n-癸烯酰氨基)乙基氨基甲酰甲硫醚类似物，包括硫醚部分、癸烯酰链中的双键以及烷基硫醚部分的修饰，被合成并比较了它们对大鼠应激性溃疡的抑制作用。用甲撑基或氧原子取代硫原子会降低药效。饱和癸烯酰链中的双键倾向于降低抗溃疡活性。癸烯酰链中双键的位置与药理活性没有关系。另一方面，具有E型构型的化合物显示出比相应的Z型化合物更强的抗溃疡活性。在9种S取代的烷基中，2-(E-2-癸烯酰氨基)乙基2-环己基乙基硫醚在大鼠中显示出最强的抗溃疡活性，在小鼠中也显示出最低的急性毒性。

  DOI：

  10.1248/cpb.39.1546
• 作为产物：
  描述：

  (Z)-5-Ethyl-decenoate 在 氢氧化钾 、 水 作用下， 以97%的产率得到(Z)-5-decenoic acid
  参考文献：
  名称：

  Bioisosteric Approach to Elucidation of Binding of the Acetate Group of a Moth Sex Pheromone Component to Its Receptor

  摘要：

  A number of analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, in which the acetate group has been replaced by functional groups that may function as bioisosters, have been synthesized and tested using single-cell electrophysiology. The activities have been interpreted in terms of the molecular electrostatic potentials of the polar functional group as calculated by ab initio quantum mechanical calculations. It is concluded that both oxygens of the acetate group in (Z)-5-decenyl acetate contribute to the interactions between the pheromone component and its receptor. Furthermore, the results indicate that the crucial interaction between the carbonyl group and the receptor, which is most probably a hydrogen bonding interaction, takes place in a direction pointing away from the hydrocarbon chain of the pheromone component.

  DOI：

  10.1023/a:1022563010599

文献信息

• Inhibitory Effect of 2-(E-2-Alkenoylamino)ethyl Alkyl Sulfides on Gastric Ulceration in Rats. II. Structure and Activity Relationships of 2-(E-n or Z-n-Decenoylamino)ethyl Alkyl Sulfides.
  作者：Isao KOHDA、Masakazu IWAI、Masahiro WATANABE、Yoshio ARAKAWA、Chikara FUKAYA、Kazumasa YOKOYAMA、Yasuhiro KOHAMA、Tsutomu MIMURA

  DOI：10.1248/cpb.39.1546

  日期：——

  The analogues of 2-(E-n or Z-n-decenoylamino)ethyl carbamoylmethyl sulfide, including the modifications of sulfide portion, double bond in decenoyl chain and alkyl sulfide moiety, were synthesized and their inhibitory effects on stress-induced ulceration in rats were compared.Replacing the sulfura atom by methylene group or oxygen atom reduced the effect of potency. Saturation of the double bond in the decenoyl chain tended to reduce the anti-ulcerogenic activity in rats. There was no relationship between the position of double bond in decenoyl chain and the pharmacological activity. On the other hand, compounds with E-configuration showed stronger anti-ulcer activity than the corresponding Z-type of compounds. Among 9 kinds of S substituted alkyl groups for carbamoylmethyl, 2-(E-2-decenoylamino)ethyl 2-cyclohexylethyl sulfide showed the most potent anti-ulcerogenic activity in rats and also showed the lowest acute toxicity in mice.

  2-(E型或Z型n-癸烯酰氨基)乙基氨基甲酰甲硫醚类似物，包括硫醚部分、癸烯酰链中的双键以及烷基硫醚部分的修饰，被合成并比较了它们对大鼠应激性溃疡的抑制作用。用甲撑基或氧原子取代硫原子会降低药效。饱和癸烯酰链中的双键倾向于降低抗溃疡活性。癸烯酰链中双键的位置与药理活性没有关系。另一方面，具有E型构型的化合物显示出比相应的Z型化合物更强的抗溃疡活性。在9种S取代的烷基中，2-(E-2-癸烯酰氨基)乙基2-环己基乙基硫醚在大鼠中显示出最强的抗溃疡活性，在小鼠中也显示出最低的急性毒性。
• In Situ Methylene Capping: A General Strategy for Efficient Stereoretentive Catalytic Olefin Metathesis. The Concept, Methodological Implications, and Applications to Synthesis of Biologically Active Compounds
  作者：Chaofan Xu、Xiao Shen、Amir H. Hoveyda

  DOI：10.1021/jacs.7b06552

  日期：2017.8.9

  catalyst-controlled stereoselective olefin metathesis considerably. By incorporation of commercially available Z-butene together with robust and readily accessible Ru-based dithiolate catalysts developed in these laboratories, a large variety of transformations can be made to proceed with terminal alkenes, without the need for a priori synthesis of a stereochemically defined disubstituted olefin. Reactions thus proceed

  原位亚甲基封端作为一种实用且广泛适用的策略被引入，可以显着扩大催化剂控制的立体选择性烯烃复分解的范围。通过将市售的 Z-丁烯与这些实验室开发的坚固且易于获得的基于 Ru 的二硫醇催化剂结合，可以进行多种转化以处理末端烯烃，而无需先验合成立体化学定义的双取代烯烃。因此，与使用其他基于 Ru、Mo 或 W 的配合物相比，反应以显着更高的效率和 Z 选择性进行。与含有羧酸、醛、烯丙醇、芳基烯烃、α取代基的烯烃交叉复分解，或氨基酸残基以 47-88% 的产率和 90:10 至 >98:2 的 Z:E 选择性生成所需产物。使用 70:30 Z-:E-丁烯混合物（原油裂解的副产品），转化同样有效且具有立体选择性。原位亚甲基封端策略与相同的儿茶酚硫醇配合物（无需催化剂修饰）一起进行闭环复分解反应，以 40-70% 的产率和 96:4-98 的产率生成 14 至 21 元环大环烯烃:2 Z:E 选择性；与
• Preparation of stereochemically pure E- and Z-alkenoic acids and their methyl esters from bicyclo[n.1.0]alkan-1-ols. Application in the synthesis of insect pheromones
  作者：D. M. Zubrytski、D. G. Kananovich、E. A. Matiushenkov

  DOI：10.1134/s107042801706001x

  日期：2017.6

  endo-alkyl- and hydroxyalkyl-substituted bicyclo[n.1.0]alkan-1-ols with (diacetoxy-λ3-iodanyl)benzene gave the corresponding methyl alkenoates exclusively with E or Z configuration of the double bond. This reaction was used as the key stage in the syntheses of stereoisomerically pure components of pest insect pheromones: (E)-dodec-9-en-1-yl acetate (European pine shoot moth Rhyacionia buoliana), (Z)-tetradec-11-en-1-yl

  的氧化裂解外-和内-烷基-和羟烷基取代的双环[ Ñ .1.0]的烷-1-醇与（乙酰氧基λ 3 -iodanyl）苯，得到相应的甲基烯酸酯只与Ë或Ž双键的构型。该反应被用作害虫昆虫信息素的立体异构纯组分合成的关键阶段：（E）-dodec-9-en-1-yl乙酸酯（欧洲松枝蛾Rhyacionia buoliana），（Z）-tetradec -11 -en-1-yl醋酸盐（欧洲橡木卷叶草Tortrix viridana）和（3 E，8 Z，11 Z）-十四烷基-3,8,11-三烯-1-基乙酸酯（番茄切叶机Tuta absoluta）。
• Semi-biosynthetic production of fatty alcohols and fatty aldehydes
  申请人：Provivi, Inc.

  公开号：US11214818B2

  公开（公告）日：2022-01-04

  The present application relates to methods of producing one or more fatty alcohols and/or one or more fatty aldehydes from one or more unsaturated lipid moieties by combining the obtainment or production of the one or more unsaturated lipid moieties from a biological source with conversion by non-biological means of the one or more unsaturated lipid moieties to one or more fatty alcohols and/or one or more fatty aldehydes. The present application also relates to recombinant microorganisms having a biosynthesis pathway for the production of one or more unsaturated lipid moieties. The one or more fatty alcohols can further be chemically converted to one or more corresponding fatty acetates. The one or more fatty alcohols, one or more fatty aldehydes and/or one or more fatty acetates produced by the methods described herein may be one or more insect pheromones, one or more fragrances, one or more flavoring agents, or one or more polymer intermediates.

  本申请涉及从一种或多种不饱和脂质分子生产一种或多种脂肪醇和/或一种或多种脂肪醛的方法，方法是将从生物来源获得或生产一种或多种不饱和脂质分子与通过非生物手段将一种或多种不饱和脂质分子转化为一种或多种脂肪醇和/或一种或多种脂肪醛结合起来。本申请还涉及具有生产一种或多种不饱和脂质分子的生物合成途径的重组微生物。一种或多种脂肪醇可进一步化学转化为一种或多种相应的脂肪乙酸酯。本文所述方法生产的一种或多种脂肪醇、一种或多种脂肪醛和/或一种或多种脂肪乙酸酯可以是一种或多种昆虫信息素、一种或多种香料、一种或多种调味剂或一种或多种聚合物中间体。
• PHEROMONDISPENSER
  申请人：BASF SE

  公开号：EP2384111A1

  公开（公告）日：2011-11-09