methyl (Z)-2-methyl-2-hexenoate | 139539-80-3

• 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 (Z)-2-methyl-2-hexenoate
• 英文别名: 2-methyl-hex-2c-enoic acid methyl ester；2-Methyl-hex-2c-ensaeure-methylester；methyl (Z)-2-methylhex-2-enoate
• CAS: 139539-80-3
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: PSOAOBLLWDXJGD-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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 (Z)-2-methyl-2-hexenoate 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 三乙基硼氢化锂 、 D-(-)-酒石酸二异丙酯 作用下， 生成 [(2S,3R)-2-methyl-3-propyloxiran-2-yl]methanol
  参考文献：
  名称：

  Jung, Michael E.; D'Amico, Denn C., Journal of the American Chemical Society, 1993, vol. 115, # 25, p. 12208 - 12209

  摘要：

  DOI：
• 作为产物：
  描述：

  2-dydroxy-2-methylhexanoic acid 在 硫酸 作用下， 生成 methyl (Z)-2-methyl-2-hexenoate
  参考文献：
  名称：

  BRANCHED-CHAIN FATTY ACIDS. XXXI. ASSIGNMENT OF GEOMETRIC CONFIGURATION IN THE 2-METHYL-2-ALKENOIC ACIDS¹

  摘要：

  DOI：

  10.1021/jo01377a012

文献信息

• Metabolites of the Anaerobic Degradation of <i>n</i> ‐Hexane by Denitrifying Betaproteobacterium Strain HxN1
  作者：Julian Küppers、Nico Mitschke、Simone Heyen、Ralf Rabus、Heinz Wilkes、Jens Christoffers

  DOI：10.1002/cbic.201900375

  日期：2020.2.3

  The constitutions of seven metabolites formed during anaerobic degradation of n-hexane by the denitrifying betaproteobacterium strain HxN1 were elucidated by comparison of their GC and MS data with those of synthetic reference standards. The synthesis of 4-methyloctanoic acid derivatives was accomplished by the conversion of 2-methylhexanoyl chloride with Meldrum's acid. The β-oxoester was reduced

  通过反硝化β变形杆菌HxN1菌株在正己烷厌氧降解过程中形成的七种代谢物的组成，通过将它们的GC和MS数据与合成参考标准品进行了比较。4-甲基辛酸衍生物的合成通过将2-甲基己酰氯与麦德鲁姆酸转化而完成。用NaBH4还原β-氧代酸酯，消除羟基，并置换双键，生成4-甲基-3-氧代辛酸酯，3-羟基-4-甲基辛酸酯，（E）-4-甲基酯-2-辛烯酸酯，以及（E）-和（Z）-4-甲基-3-辛烯酸酯。类似地，由丁酰氯和Meldrum酸制备2-甲基-3-氧己酸酯和3-羟基-2-甲基己酸酯的甲酯。然而，通过Horner-Wadsworth-Emmons反应制备（E）-2-甲基-2-己烯酸甲酯，然后异构化为（E）-2-甲基-3-己烯酸甲酯。除了在培养物中无法检测到的4-甲基-3-氧代辛酸酯外，这项研究完成了对正己烷厌氧降解为2-甲基-3-氧代己酰基辅酶A（CoA）的所有中间体的明确鉴定。 ），然后将其硫解切割成
• A FACILE ONE-POT SYNTHESIS OF METHYL(2E)-2-METHYLALK-2-ENOATES FROM BAYLIS-HILLMAN ADDUCTS UNDER MICROWAVE IRRADIATION
  作者：Subramanian Ravichandran

  DOI：10.1081/scc-100104425

  日期：2001.1

  A facile procedure for the synthesis of the title compound is described.
• Stereospecific nucleophilic addition reactions to olefins. Addition of thiols to .alpha.,.beta.-unsaturated carboxylic acid derivatives
  作者：Okiko Miyata、Tetsuro Shinada、Ichiya Ninomiya、Takeaki Naito、Tadamasa Date、Kimio Okamura、Satoshi Inagaki

  DOI：10.1021/jo00023a021

  日期：1991.11

  Stereospecific nucleophilic addition of thiols to derivatives of alpha,beta-unsaturated carboxylic acids is described. The additions are carried out at room temperature in the presence of a catalytic amount of lithium thiolate and an excess of thiol as a proton source. Erythro and threo adducts are obtained with high diasteroselectivity from E and Z olefins, respectively. This anti addition suggests that the enolate generated by nucleophilic addition undergoes rapid protonation prior to conformational change in the intermediate.