Methyl (E/Z)-3-methyl-2-dodecenoate | 38976-39-5

• 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: Methyl (E/Z)-3-methyl-2-dodecenoate
• 英文别名: methyl (E)-3-methyldodec-2-enoate；3-methyl-dodec-2-enoic acid methyl ester；3-Methyl-dodec-2-ensaeure-methylester；methyl 3-methyl-2-dodecenoate
• CAS: 38976-39-5
• 化学式: C₁₄H₂₆O₂
• 分子量: 226.359
• InChiKey: JZLCLHMKXWJMOR-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  Methyl (E/Z)-3-methyl-2-dodecenoate 在 lithium aluminium tetrahydride 、 溴 、 magnesium 、 三苯基膦 、 copper(l) chloride 、 mercury dichloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 7.0h， 生成 (E)-6-methyl-pentadec-5-en-1-yne
  参考文献：
  名称：

  Mori, Kenji; Uenishi, Keiji, Liebigs Annalen, 1996, # 1, p. 1 - 6

  摘要：

  DOI：
• 作为产物：
  描述：

  2-十一酮 生成 Methyl (E/Z)-3-methyl-2-dodecenoate
  参考文献：
  名称：

  法呢基焦磷酸合成酶的底物特异性。

  摘要：

  DOI：

  10.1021/ja00774a045

文献信息

• Pheromone study on acarid mites. Part IX. Syntheses of alarm pheromone analogues of the mold mite, Tyrophagus putrescentiae, and their biological activities.
  作者：Yasumasa KUWAHARA、Lica SAKUMA

  DOI：10.1271/bbb1961.46.1855

  日期：——

  Against the mold mite, Tyrophagus putrescentiae, 3, 7-dimethyl-(Z)-2-octenyl formate (II) is the most active compound as an alarm pheromone besides the natural pheromone, neryl formate (I), and this activity is equal to I (1-10ppm). In order to elucidate the structural requisites for inducing alarm pheromone activity, a total of 16 analogues of I were prepared by modifying the structure of II. For preparation of 3-methyl- and 3-ethyl-(Z)-2-alkenyl formates, the Wittig reaction of ethoxy- or methoxy-carbonylmethylene triphenyl phosphorane with 2-alkanone or 3-alkanone was used. The reaction with 2-alkanone gave a mixture of (Z)-2-alkenoate (ca. 40%) and (E)-2-alkenoate (ca. 60%) in an average 60% yield. The reaction with 3-alkanone gave a mixture of (Z)-2-alkenoate (56%) and (E)-2-alkenonate (44%). Alarm pheromone activities were demonstrated on 14 compounds of (Z)-2-alkenyl formates. The presence of the (Z)-allylic primary alcohol formate moiety in a molecule was clarified as the key to induce pheromone activity, and no necessity for an acyclic monoterpene carbon skeleton was demonstrated.

  针对霉菌螨（Tyrophagus putrescentiae），3, 7-二甲基-(Z)-2-辛烯酸甲酯（II）是除了天然信息素（奈尔酸甲酯 I）外，作为警报信息素最活跃的化合物，其活性与 I 相当（1-10ppm）。为了阐明诱导警报信息素活性的结构要求，制备了16个 I 的类似物，通过改造 II 的结构。为制备3-甲基和3-乙基-(Z)-2-烯酸甲酯，采用了乙氧基或甲氧基碳酰基甲烯三苯基膦与2-烷酮或3-烷酮的威蒂格反应。与2-烷酮的反应产生了约40%的(Z)-2-烯酸酯和约60%的(E)-2-烯酸酯，平均产率为60%。与3-烷酮的反应则得到了56%的(Z)-2-烯酸酯和44%的(E)-2-烯酸酯。在14种(Z)-2-烯酸甲酯化合物中展示了警报信息素活性。研究表明，分子中存在(Z)-烯丙基初级醇酸甲酯基团是诱导信息素活性的关键，且不需要非环状单萜碳骨架。
• Novel aliphatic compounds, process for their preparation and their usage
  申请人：——

  公开号：US20040014816A1

  公开（公告）日：2004-01-22

  The present invention provides an aliphatic compound represented by the following formula (I) or pharmacologically acceptable salts thereof: 1 where n denotes an integer of 1 to 11, and 1 denotes an integer of 1 to 16, the aliphatic compound being an optical isomer of the (2R,3S,2′S) configuration when the 8-position thereof is a double bond, or an optical isomer of the (2S,3R,2′RS) configuration when the 8-position is a single bond; methods for producing the compound or pharmacologically acceptable salts thereof; and uses of the compound in the treatment of cardiovascular diseases (e.g. arteriosclerosis, cardiac diseases), cancer, rheumatism, diabetic retinopathy, and respiratory diseases.

  本发明提供了一种由以下式（I）表示的脂肪族化合物或其药理学上可接受的盐：其中n表示1到11的整数，l表示1到16的整数，当其8位点为双键时，该脂肪族化合物为（2R,3S,2′S）构型的光学异构体，或者当8位点为单键时，为（2S,3R,2′RS）构型的光学异构体；制备该化合物或其药理学上可接受的盐的方法；以及该化合物在治疗心血管疾病（如动脉硬化、心脏疾病）、癌症、风湿病、糖尿病视网膜病变和呼吸系统疾病中的用途。
• Mild, Efficient, and Robust Method for Stereocomplementary Iron-Catalyzed Cross-Coupling Using (E)- and (Z)-Enol Tosylates
  作者：Yoo Tanabe、Hiroshi Nishikado、Hidefumi Nakatsuji、Kanako Ueno、Ryohei Nagase

  DOI：10.1055/s-0030-1258131

  日期：2010.9

  Iron-catalyzed cross-coupling of Grignard reagents (RMgX) with (E)- and (Z)-enol tosylates proceeded smoothly to give a variety of the corresponding (E)- and (Z)-trisubstituted α,β-unsaturated methyl esters (total 30 examples; 55-98% yield). The simple, mild, stereoretentive method utilized iron(III) chloride (FeCl3), iron(III) acetylacetonate [Fe(acac)3], and iron(III) tris(dibenzylmethane) [Fe(dbm)3]. The (E)- and (Z)-enol tosylates were readily prepared by the reported stereocomplementary tosylation method from methyl β-keto esters or α-formyl esters. Methyl α-formyl esters were obtained via a practical and robust TiCl4-Et3N-mediated α-formylation of methyl esters with methyl formate.

  铁催化的格氏试剂（RMgX）与（E）和（Z）-醇托烷基化合物的交叉耦合反应顺利进行，产生了多种相应的（E）和（Z）-三取代的α,β-不饱和甲基酯（共30个实例；产率55-98%）。该简单、温和、保持立体选择性的反应方法使用了氯化铁（FeCl3）、醋酸乙酯铁（Fe(acac)3）和铁（III）三（二苯基甲烷）[Fe(dbm)3]。而（E）和（Z）-醇托烷基化合物是通过已报道的立体互补托烷基化方法，从甲基β-酮酯或α-甲醛酯中方便制备的。甲基α-甲醛酯通过一种实用且稳健的TiCl4-Et3N催化的甲基酯与甲基甲酸酯的α-甲醛化反应获得。
• 2-Phenylethylamides of a novel lipid acid; atrial stimulants from the soft coral Sinularia flexibilis
  作者：R Kazlauskas、JF Marwood、RJ Wells

  DOI：10.1071/ch9801799

  日期：——

  Three amides derived from tyramine, 4-(2-aminoethyl)-2-methoxyphenol and 5-(2-aminoethyl)-2-methoxyphenol and a novel lipid acid, (Z)-3- methyldodec-2-enoic acid, were isolated from the soft coral Sinularia flexibilis. The structures, obtained by spectral methods, were confirmed by synthesis.

  从 酪胺、4-(2-氨乙基)-2-甲氧基苯酚和 5-(2-氨乙基)-2-甲氧基苯酚的三种酰胺以及新型脂酸 和一种新型脂酸--(Z)-3-甲基十二-2-烯酸。 和新型脂酸。通过光谱方法获得的结构 通过合成得到了证实。
• NOVEL ALIPHATIC COMPOUNDS, PROCESS FOR THEIR PREPARATION AND THEIR USAGE
  申请人：Maruha Corporation

  公开号：EP1325904A1

  公开（公告）日：2003-07-09

  The present invention provides an aliphatic compound represented by the following formula (I) or pharmacologically acceptable salts thereof:    where n denotes an integer of 1 to 11, and l denotes an integer of 1 to 16, the aliphatic compound being an optical isomer of the (2R,3S,2'S) configuration when the 8-position thereof is a double bond, or an optical isomer of the (2S,3R,2'RS) configuration when the 8-position is a single bond; methods for producing the compound or pharmacologically acceptable salts thereof; and uses of the compound in the treatment of cardiovascular diseases (e.g. arteriosclerosis, cardiac diseases), cancer, rheumatism, diabetic retinopathy, and respiratory diseases.

  本发明提供了由下式(I)代表的脂肪族化合物或其药理学上可接受的盐： 其中 n 表示 1 至 11 的整数，l 表示 1 至 16 的整数、 当 8 位为双键时，该脂肪族化合物为(2R,3S,2'S)构型的光学异构体；当 8 位为单键时，该脂肪族化合物为(2S,3R,2'RS)构型的光学异构体；生产该化合物或其药理学上可接受的盐的方法；以及该化合物在治疗心血管疾病（如动脉硬化、心脏病）、癌症、风湿病、糖尿病视网膜病变和呼吸系统疾病中的用途。