2-Methyl-3,5-dioxohexansaeure-methylester | 94632-42-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-Methyl-3,5-dioxohexansaeure-methylester
• 英文别名: methyl 2-methyl-3,5-diketohexanoate；methyl 2-methyl-3,5-dioxohexanoate
• CAS: 94632-42-5
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: CIQLOCDZIYLZIN-UHFFFAOYSA-N

物化性质

• 沸点：
  233.3±15.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Methyl-3,5-dioxohexansaeure-methylester 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 丁酮 、 苯 为溶剂， 反应 4.5h， 生成 4-methoxy-3,6-dimethyl-2H-pyran-2-one
  参考文献：
  名称：

  Total Synthesis of (−)-Solanapyrone A via Enzymatic Diels−Alder Reaction of Prosolanapyrone

  摘要：

  The syntheses of prosolanapyrones I (6) and II (7) via the aldol reactions of pyrone and dienal segments have been achieved in five steps in 31% overall yield for 6 and seven steps in 5% overall yield for 7. An improved synthetic route starting from vinylpyrone 27 provided 7 in 11 steps in 12% overall yield. The enzymatic Diels-Alder reaction of 7 affords (-)-solanapyrone A (1) with high enantioselectivity and with good exo-selectivity, which is difficult to attain by chemical methods. In addition, a crude enzyme preparation from Alternaria solani has been used to perform a kinetic resolution of(+/-)-3.

  DOI：

  10.1021/jo980743r
• 作为产物：
  描述：

  Copper(II); (Z)-5-methoxycarbonyl-4-oxo-hex-2-en-2-olate 在 sodium hydride 、 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以88%的产率得到2-Methyl-3,5-dioxohexansaeure-methylester
  参考文献：
  名称：

  Total Synthesis of (−)-Solanapyrone A via Enzymatic Diels−Alder Reaction of Prosolanapyrone

  摘要：

  The syntheses of prosolanapyrones I (6) and II (7) via the aldol reactions of pyrone and dienal segments have been achieved in five steps in 31% overall yield for 6 and seven steps in 5% overall yield for 7. An improved synthetic route starting from vinylpyrone 27 provided 7 in 11 steps in 12% overall yield. The enzymatic Diels-Alder reaction of 7 affords (-)-solanapyrone A (1) with high enantioselectivity and with good exo-selectivity, which is difficult to attain by chemical methods. In addition, a crude enzyme preparation from Alternaria solani has been used to perform a kinetic resolution of(+/-)-3.

  DOI：

  10.1021/jo980743r

文献信息

• Effenberger, Franz; Schoenwaelder, Karl-Heinz, Chemische Berichte, 1984, vol. 117, # 11, p. 3270 - 3279
  作者：Effenberger, Franz、Schoenwaelder, Karl-Heinz

  DOI：——

  日期：——
• EFFENBERGER, F.;SCHOENWAELDER, K. -H., CHEM. BER., 1984, 117, N 11, 3270-3279
  作者：EFFENBERGER, F.、SCHOENWAELDER, K. -H.

  DOI：——

  日期：——
• Total Synthesis of (−)-Solanapyrone A via Enzymatic Diels−Alder Reaction of Prosolanapyrone
  作者：Hideaki Oikawa、Tomonori Kobayashi、Kinya Katayama、Yuichi Suzuki、Akitami Ichihara

  DOI：10.1021/jo980743r

  日期：1998.11.1

  The syntheses of prosolanapyrones I (6) and II (7) via the aldol reactions of pyrone and dienal segments have been achieved in five steps in 31% overall yield for 6 and seven steps in 5% overall yield for 7. An improved synthetic route starting from vinylpyrone 27 provided 7 in 11 steps in 12% overall yield. The enzymatic Diels-Alder reaction of 7 affords (-)-solanapyrone A (1) with high enantioselectivity and with good exo-selectivity, which is difficult to attain by chemical methods. In addition, a crude enzyme preparation from Alternaria solani has been used to perform a kinetic resolution of(+/-)-3.