(E)-Methyl 2-methyl-4-oxo-2-hexenoate | 115546-12-8

• 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: (E)-Methyl 2-methyl-4-oxo-2-hexenoate
• 英文别名: methyl (E)-2-methyl-4-oxo-2-hexenoate；methyl (E)-2-methyl-4-oxohex-2-enoate
• CAS: 115546-12-8
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: FDLRJOJYXUTRQV-AATRIKPKSA-N

物化性质

• 沸点：
  237.4±23.0 °C(Predicted)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  4
• 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：

  (E)-Methyl 2-methyl-4-oxo-2-hexenoate 在 palladium on activated charcoal lithium hydroxide 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 间氯过氧苯甲酸 、 calcium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 36.0h， 生成 麦皮星酮
  参考文献：
  名称：

  Total Synthesis of Mappicine Ketone (Nothapodytine B) by Means of Sulfur-Directed 5-exo-Selective Aryl Radical Cyclization onto Enamides

  摘要：

  Enamides 5, on treatment with Bu3SnH-AIBN, underwent aryl radical cyclization in a 5-exo manner to give 1-[bis(phenylthio)methyl]dihydroisoindoles 6, which were partially desulfurized with Bu3SnH-AIBN to give 1-mono(phenylthio)methyl congeners 7. Formation of 6 from 5 may be explained by the presence of two phenylthio groups at the terminus of the N-vinylic bond of 5, since enamide Sa having no phenylthio group underwent aryl radical cyclization in a 6-endo manner. Compound 7d (R = CF3) was transformed into sulfoxide 16, which was treated with (CF3CO)(2)O and then with 10% NaOH to give a model compound 20 of mappicine ketone (MPK) (1) through aldol condensation of aldehyde 18. An attempt to synthesize MPK using this method with sulfoxide 28 prepared from 25, however, was unsuccessful, and, instead, photochemical cyclization of enamide 38 prepared from 25 furnished MPK.

  DOI：

  10.1021/jo030177m
• 作为产物：
  描述：

  丙酮酸甲酯 、 1-(三苯基膦)-2-丁酮 以 苯 为溶剂， 反应 22.0h， 以86%的产率得到(E)-Methyl 2-methyl-4-oxo-2-hexenoate
  参考文献：
  名称：

  The Synthesis of 4-Oxo-2-pentenoic Esters by Wittig Reaction Using α-Oxoesters

  摘要：

  稳定的耦合物与α-氧酯的反应可高产率地生成4-氧代-2-戊烯酸酯。通过对每个反应物进行适当取代，可以大量制备高度取代和受阻的烯酮，且具有优异的几何选择性。

  DOI：

  10.1055/s-1987-28168

文献信息

• Acrylic adhesive compositions containing ketonyl (meth)acrylate
  申请人：——

  公开号：US20030032736A1

  公开（公告）日：2003-02-13

  Use of a ketonyl [meth]acrylate as a replacement for at least a substantial portion of the content of hydroxy (lower alkyl) methacrylate in a curable acrylic adhesive composition. Suitably the ketonyl [meth]acrylate is of the formula: 1 wherein: R 1 is H or C 1 -C 5 alkyl, particularly C 1 -C 2 alkyl;R 2 is C 1 -C 5 alkyl, cyclohexyl, phenyl, benzyl, or substituted derivatives of any of the foregoing; and n is 1-5, for example acetonyl methacrylate.

  使用酮基[甲基]丙烯酸酯替代可固化丙烯酸粘合剂组合物中至少大部分羟基（低级烷基）甲基丙烯酸酯的含量。 合适的酮基甲基丙烯酸酯的结构式为 1 其中R 1 是 H 或 C 1 -C 5 烷基，特别是 C 1 -C 2 烷基；R 2 是 C 1 -C 5 烷基、环己基、苯基、苄基或上述任一物质的取代衍生物；n 为 1-5，例如甲基丙烯酸丙酮酯。
• SCHUDA, PAUL FRANCIS;EBNER, CYNTHIA B.;POTLOCK, STEVEN J., SYNTHESIS,(1987) N 12, 1055-1057
  作者：SCHUDA, PAUL FRANCIS、EBNER, CYNTHIA B.、POTLOCK, STEVEN J.

  DOI：——

  日期：——
• [EN] ACRYLIC ADHESIVE COMPOSITIONS CONTAINING KETONYL (METH)ACRYLATE<br/>[FR] COMPOSITIONS ADHESIVES ACRYLIQUES CONTENANT DU CETONYL(METH)ACRYLATE
  申请人：LOCTITE R & D LTD

  公开号：WO2001051576A1

  公开（公告）日：2001-07-19

  Use of a ketonyl [meth]acrylate as a replacement for at least a substantial portion of the content of hydroxy (lower alkyl) methacrylate in a curable acrylic adhesive composition. Suitably the ketonyl [meth]acrylate is of the formula (1), wherein: R1 is H or C1-C5 alkyl, particularly C1-C2 alkyl; R2 is C1-C5 alkyl, cyclohexyl, phenyl, benzyl, or substituted derivatives of any of the foregoing; and n is 1-5, for example acetonyl methacrylate.
• Total Synthesis of Mappicine Ketone (Nothapodytine B) by Means of Sulfur-Directed 5-<i>exo</i>-Selective Aryl Radical Cyclization onto Enamides
  作者：Issei Kato、Masayuki Higashimoto、Osamu Tamura、Hiroyuki Ishibashi

  DOI：10.1021/jo030177m

  日期：2003.10.1

  Enamides 5, on treatment with Bu3SnH-AIBN, underwent aryl radical cyclization in a 5-exo manner to give 1-[bis(phenylthio)methyl]dihydroisoindoles 6, which were partially desulfurized with Bu3SnH-AIBN to give 1-mono(phenylthio)methyl congeners 7. Formation of 6 from 5 may be explained by the presence of two phenylthio groups at the terminus of the N-vinylic bond of 5, since enamide Sa having no phenylthio group underwent aryl radical cyclization in a 6-endo manner. Compound 7d (R = CF3) was transformed into sulfoxide 16, which was treated with (CF3CO)(2)O and then with 10% NaOH to give a model compound 20 of mappicine ketone (MPK) (1) through aldol condensation of aldehyde 18. An attempt to synthesize MPK using this method with sulfoxide 28 prepared from 25, however, was unsuccessful, and, instead, photochemical cyclization of enamide 38 prepared from 25 furnished MPK.
• The Synthesis of 4-Oxo-2-pentenoic Esters by Wittig Reaction Using α-Oxoesters
  作者：Paul Francis Schuda、Cynthia B. Ebner、Steven J. Potlock

  DOI：10.1055/s-1987-28168

  日期：——

  The reaction of stabilized ylides with α-oxoesters gives high yields of 4-oxo-2-pentenoic esters. By suitable substitution of each reactant, highly substituted and hindered enones can be prepared in quantity, with excellent geometric selectivity.

  稳定的耦合物与α-氧酯的反应可高产率地生成4-氧代-2-戊烯酸酯。通过对每个反应物进行适当取代，可以大量制备高度取代和受阻的烯酮，且具有优异的几何选择性。