反式-3-癸烯酸甲酯 | 51826-93-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 反式-3-癸烯酸甲酯
• 英文名称: trans-3-decenoic acid methyl ester
• 英文别名: (E)-methyl dec-3-enoate；methyl (E)-dec-3-enoate；Methyl (E)-3-Decenoate；methyl (3E)-decenoate；methyl 3-decenoate；Methyl trans-3-decenoat
• CAS: 51826-93-8
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: HLXICRJOFXSTBV-CMDGGOBGSA-N

物化性质

• 沸点：
  232.8±9.0 °C(Predicted)
• 密度：
  0.889±0.06 g/cm3(Predicted)
• 保留指数：
  1321

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反式-3-癸烯酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以99%的产率得到(E)-癸-3-烯-1-醇
  参考文献：
  名称：

  [EN] CYCLOALKYL-CONTAINING CARBOXYLIC ACIDS AND USES THEREOF
  [FR] ACIDES CARBOXYLIQUES CONTENANT UN CYCLOALKYLE ET LEURS UTILISATIONS

  摘要：

  本申请公开了化合物的结构式(I)或其盐：(I)，以及包含该化合物或其盐的组合物。还公开了利用该化合物、其盐或包含相同成分的组合物治疗受试者的贫血或白细胞减少症、纤维化、癌症、高血压和/或代谢状况的用途。

  公开号：

  WO2021124272A1
• 作为产物：
  描述：

  (2Z)-癸烯酸甲酯 生成 反式-3-癸烯酸甲酯
  参考文献：
  名称：

  New type of cyclization of .alpha.,.beta.,.chi.,.psi.-unsaturated dioic acid esters through tandem conjugate additions by using lithium N-benzyl-N-(trimethylsilyl)amide as a nitrogen nucleophile

  摘要：

  Treatment of dimethyl (2E,6E)-2,6-octadienedioate with lithium N-benzyl-N-(trimethylsilyl)amide (LSA) gave 5-exo-trig ring closure products, methyl 3-(N-benzylamino)-2-(methoxycarbonyl)cyclopentane-1-acetates, through tandem conjugate additions. The related 6-exo-trig cyclization proceeded stereoselectively to give ethyl c-3-(N-benzylamino)-t-2-(ethoxycarbonyl)cyclohexane-1-acetate. In contrast with the 5- and 6-exo-trig cyclization, no 7-exo-trig cyclization occurred. The 5-exo-trig cyclization products were converted into 2-(methoxycarbonyl)-2-cyclopentene-1-carboxylic acid methyl ester in an excellent yield. 5-exo-trig cyclization of the unsymmetrical dienedioate consisting of crotonate and (E)-2-methyl-2-butenoate units proceeded regioselectively through conjugate addition of LSA to the crotonate part. Similar regioselectively was observed in the case of 5-exo-trig cyclization of the dienedioate possessing crotonate and (E)-3-methyl-2-pentenoate units. Total syntheses of the physiologically active cyclopentane monoterpenes (+/-)-dihydronepetalactone and (+/-)-isohydronepetalactone has been accomplished by this cyclization strategy. In addition, it has been demonstrated that LSA is a more efficient nitrogen nucleophile than LDA to cyclize omega-halo-alpha,beta-unsaturated esters.

  DOI：

  10.1021/jo00037a034

文献信息

• A versatile and convenient protocol for the stereocontrolled synthesis of olefinic insect pheromones
  作者：Andrei A. Vasil'ev、Alexei L. Vlasyuk、Galina D. Gamalevich、Edward P. Serebryakov

  DOI：10.1016/0968-0896(96)00016-8

  日期：1996.3

  supplemented by an enzymatic hydrolysis, was successfully applied to the synthesis of configurationally pure (gp > or = 98%) pheromones of the furniture carpet beetle, dry bean beetle, rusty grain beetle, square-necked grain beetle and a trail-following pheromone mimic for subterranean termites.

  2,4-二烯酸烷基酯的Horner-Emmons合成与在复杂的L.Cr（CO）3催化剂（L = 3CO或芳烃）上的氢化反应相结合，提供了一种通用的，立体控制的且操作简单的方法（Z）-二取代的（Z）-三取代的（E）-三取代的烯烃和跳过的（Z，Z）-二取代的二烯烃具有均聚物类型的功能。该方案，有时还辅以酶促水解，已成功地应用于家具地毯甲虫，干豆甲虫，生锈的谷物甲虫，方颈谷物甲虫和小径的构型纯（gp>或= 98％）信息素的合成信息素模仿地下白蚁。
• Metabolism of Deuterated<i>erythro</i>‐Dihydroxy Fatty Acids in<i>Saccharomyces cerevisiae</i>: Enantioselective Formation and Characterization of Hydroxylactones
  作者：Leif‐A. Garbe、Katja Morgenthal、Katrin Kuscher、Roland Tressl

  DOI：10.1002/hlca.200890129

  日期：2008.6

  Epoxides of fatty acids are hydrolyzed by epoxide hydrolases (EHs) into dihydroxy fatty acids which are of particular interest in the mammalian leukotriene pathway. In the present report, the analysis of the configuration of dihydroxy fatty acids via their respective hydroxylactones is described. In addition, the biotransformation of (±)-erythro-7,8- and -3,4-dihydroxy fatty acids in the yeast Saccharomyces

  脂肪酸的环氧化合物被环氧水解酶（EHs）水解为二羟基脂肪酸，这在哺乳动物白三烯途径中特别重要。在本报告中，描述了通过其各自的羟基内酯对二羟基脂肪酸构型的分析。另外，通过GC / EI-MS分析表征了酵母酿酒酵母中（±）-赤型-7，8-和-3，4-二羟基脂肪酸的生物转化。化学合成的（±）的生物转化-赤-7,8-二羟基（7,8- 2 ħ 2）十四烷酸（（±） -赤- 1）在酵母酿酒酵母导致形成5,6-二羟基（5,6- 2 H 2）十二酸（6），将其内酯化为（5 S，6 R）-6-羟基（5,6- 2 H 2）十二酸具有86％ee的-5-内酯（（5 S，6 R）-4）进入赤型-5-羟基（5,6- 2 H 2）十二烷-6-内酯（erythro - 8）。另外，该α -ketols 7-羟基-8-氧代（7- 2 ħ 1）十四烷酸（图9a）和8-羟基-7-氧代（8- 2检测到H 1）十四烷酸（9b）作为中间体。6的进一步代谢产生3
• Synthesis of carboxylic esters using formaldehyde dimethyl dithioacetal S,S-dioxide
  作者：Katsuyuki Ogura、Jun-ichi Watanabe、Hirotada Iida

  DOI：10.1016/s0040-4039(01)93025-4

  日期：——

  Formaldehyde dimethyl dithioaoetal S,S-dioxide () reacted uith an alkyl bromide or a 2-alkenyl bromide () under phase-transfer sonditions using 50% aq. NaOH to give an alkyl or 2-alkenyl derivative of , whereas, in the reaction with in the presence of Kg2CO3KI in HMPA, formed a 1-alken-3-yl derivative. Transformation of these products into the corresponding carboxylio esters uae also described.

  甲醛二甲基二硫代缩醛S，S-二氧化物（）在烷基转移或2-烯基溴（）的作用下，使用50％HCl水溶液进行反应。NaOH生成的烷基或2-烯基衍生物，而在HMPA中与Kg 2 CO 3 KI存在下反应，形成1-烯-3-基衍生物。还描述了将这些产物转化成相应的羧基酯。
• A general approach to γ-lactones via osmium-catalyzed asymmetric dihydroxylation. Synthesis of (−)- and (+)-muricatacin.
  作者：Zhi-Min Wang、Xiu-Lian Zhang、K.Barry Sharpless、Subhash C. Sinha、Anjana Sinha-Bagchi、Ehud Keinan

  DOI：10.1016/s0040-4039(00)79001-0

  日期：1992.10

  γ-lactones have been prepared highly enantioselectively (92–99% ee) using either AD-mix-β or AD-mix-α with both β,γ- and γ,δ-unsaturated esters. The method is exemplified by the three-step synthesis of (−) and (+)-muricatacin in 74% yield and >99% ee.

  使用AD-mix-β或AD-mix-α和β，γ-和γ，δ-不饱和酯对羟基γ-内酯的两种对映体进行了高对映选择性（92-99％ee）。该方法以三步合成（-）和（+）-多卡他霉素为例，产率为74％，ee大于99％。
• REGIOSELECTIVE OXIDATION OF INTERNAL OLEFINS BEARING NEIGHBORING OXYGEN FUNCTIONS BY MEANS OF PALLADIUM CATALYSTS. A DIRECT PREPARATION OF γ-KETO ESTERS AND 1,4-DIKETONES FROM β,γ-UNSATURATED ESTERS AND KETONES
  作者：Hideo Nagashima、Kiyomi Sakai、Jiro Tsuji

  DOI：10.1246/cl.1982.859

  日期：1982.6.5

  γ-Keto esters and 1,4-diketones were prepared by the palladium-catalyzed regioselective oxidation of β,γ-unsaturated esters and ketones. The best yields were obtained when the reaction was carried out using PdCl2/CuCl/O2 catalyst system in aqueous dioxane.

  通过钯催化的β,γ-不饱和酯和酮的区域选择性氧化制备γ-酮酯和1,4-二酮。当反应在二恶烷水溶液中使用 PdCl2/CuCl/O2 催化剂体系进行时，获得最佳产率。