Methyl (E)-4-oxo-2-heptenoate | 108087-17-8

• 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)-4-oxo-2-heptenoate
• 英文别名: 4-oxo-hept-2t-enoic acid methyl ester；4-Oxo-hept-2t-ensaeure-methylester；methyl (E)-4-oxohept-2-enoate
• CAS: 108087-17-8
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: PCPIFYUUXNXLPN-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl (E)-4-oxo-2-heptenoate 在 盐酸 、 溶剂黄146 作用下， 生成 (E)-4-oxohept-2-enoic acid
  参考文献：
  名称：

  Ernest; Jelinkova, Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 3341,3345

  摘要：

  DOI：
• 作为产物：
  描述：

  4-Oxo-3-tosylheptanoic acid 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl (E)-4-oxo-2-heptenoate
  参考文献：
  名称：

  Lithium 3-Lithio-3-tosylalkanoates: .beta.-Acylvinyl Anion Equivalents of .beta.-Lithiated .alpha.,.beta.-Unsaturated Carboxylic Acids

  摘要：

  The dilithiation of beta-tosylated propanoic, 2-methylpropanoic, and butanoic acid 10 with n-butyllithium at -78 degrees C leads to the corresponding lithium 3-lithio-3-tosylalkanoates 11. They react with different electrophilic reagents (deuterium oxide, iodine, trimethylchlorosilane, alkyl halides, and acyl chlorides) to give the corresponding 3-substituted tosylated alkanoic acids 12. When carbonyl compounds are allowed to react with intermediates 11 followed by in situ lactonization with trifluoracetic anhydride and base-promoted elimination alpha,beta-butenolides are obtained. This methodology is applied to the direct synthesis of the rosefuran lactone precursor 14cg, the O-benzyl derivative of (+/-)-umbelactone (14ch), and (+/-)-andirolactone (14ci). The alkylation and acylation reactions of organolithium compounds 11 followed by esterification with hydrogen chloride in methanol and treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afford alpha,beta- and/or beta,gamma-unsaturated esters 17 and/or 18 and unsaturated 4-keto esters 19, respectively. The last methodology has been applied to the synthesis of the unsaturated 4-keto ester 19ae precursor of the seco acid of (+/-)-pyrenophorin (22).

  DOI：

  10.1021/jo00090a043

文献信息

• Cobalt(II) catalysed reaction of alkenes with aliphatic aldehydes and molecular oxygen: scope and mechanism
  作者：Sonika Bhatia、T. Punniyamurthy、Beena Bhatia、Javed Iqbal

  DOI：10.1016/s0040-4020(01)87194-5

  日期：1993.7

  prepared using Schiff's bases derived from aromatic aldehydes and amines or α-aminoesters. These complexes are versatile catalyst for the reaction between aliphatic aldehydes and various alkenes. The outcome of the reaction is controlled by the electronic nature of the alkene as the electron deficient alkenes undergo oxidative addition of aldehydes followed by dioxygen incorporation to yield 2-hydr

  可以使用衍生自芳族醛和胺或α-氨基酯的席夫碱制备各种钴（II）配合物。这些络合物是脂肪族醛与各种烯烃之间反应的通用催化剂。反应的结果受烯烃的电子性质控制，因为缺电子的烯烃经历醛的氧化加成反应，然后引入双氧生成2-羟基（酰氧基）-4-氧酸酯或腈，而未活化或富电子的烯烃则提供了相应的环氧化物。这些反应是通过自由基途径进行的，并提出了一种常见的酰基钴中间体，用于形成4和环氧化物7。
• A Convenient Method for the Preparation of Methyl<i>trans</i>-4-Oxo-2-alkenoates
  作者：O. G. Kulinkovich、I. G. Tischenko、J. N. Romashin、L. N. Savitskaya

  DOI：10.1055/s-1986-31640

  日期：——

  Methyl trans-4-oxo-2-alkenoates are synthesized in 64-93% yields by successive treatment of 5-substituted 2,2-dimethoxy-2,3-dihydrofurans with N-bromosuccinimide in aqueous acetone and triethylamine in ether.

  甲基反-4-氧代-2-烯酸酯通过将5-取代的2,2-二甲氧基-2,3-二氢呋喃分别与溴代琥珀酰亚胺在水相丙酮和醚相三乙胺中处理，合成的产率为64-93%。
• KULINKOVICH, O. G.;TISCHENKO, I. G.;ROMASHIN, J. N.;SAVITSKAYA, L. N., SYNTHESIS, BRD, 1986, N 5, 378-379
  作者：KULINKOVICH, O. G.、TISCHENKO, I. G.、ROMASHIN, J. N.、SAVITSKAYA, L. N.

  DOI：——

  日期：——
• NAKAYAMA MITSURU; SHINKE SHUZO; MATSUSHITA YOICHI; OHIRA SUSUMU; HAYASHI +, BULL. CHEM. SOC. JAP., 1979, 52, NO 1, 184-185
  作者：NAKAYAMA MITSURU、 SHINKE SHUZO、 MATSUSHITA YOICHI、 OHIRA SUSUMU、 HAYASHI +

  DOI：——

  日期：——