4-methyl-2-pentenal diethyl acetal | 344423-09-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methyl-2-pentenal diethyl acetal
• 英文别名: 1,1-diethoxy-4-methylpent-2-ene；(E)-1,1-Diethoxy-4-methyl-pent-2-ene；(E)-1,1-diethoxy-4-methylpent-2-ene
• CAS: 344423-09-2
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: CHFRHBQKSZSKSU-BQYQJAHWSA-N

物化性质

• 沸点：
  79-80 °C(Press: 20 Torr)
• 密度：
  0.858±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-2-pentenal diethyl acetal 以20%的产率得到
  参考文献：
  名称：

  BESTMANN, H. J.;ROTH, K.;ETTLINGER, M., CHEM. BER., 1982, 115, N 1, 161-171

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-4-methylpent-2-enal 、 原甲酸三乙酯 在 硝酸铵 作用下， 以 乙醇 为溶剂， 以85%的产率得到4-methyl-2-pentenal diethyl acetal
  参考文献：
  名称：

  Remote Stereocontrol in the Nazarov Reaction:  A New Approach to the Core of Roseophilin

  摘要：

  Three different procedures are compared to obtain properly substituted divinyl ketones in which one of the double bonds is embedded in a five-membered heterocyclic structure and therefore suitable to produce cyclopenta-fused pyrrole derivatives by the acid-catalyzed Nazarov reaction. These, on treatment with TFA, afforded 2,4-cis-disubstituted 2,3,4,5-tetrahydro-1H-cyclopenta[b]pyrrol-6-ones with high stereocontrol. One of these Nazarov products was oxidized to the corresponding 4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one derivative, thus obtaining an enantiopure key intermediate in the total synthesis of roseophilin.

  DOI：

  10.1021/jo0504058

文献信息

• Stereoselective Synthesis of Spirocyclic Ketones by Nazarov Reaction
  作者：Cristina Prandi、Annamaria Deagostino、Paolo Venturello、Ernesto G. Occhiato

  DOI：10.1021/ol051464a

  日期：2005.9.1

  [reaction: see text] The Suzuki-Miyaura cross-coupling reaction between alpha-ethoxydienyl boronates and lactone-derived vinyl triflates affords functionalized 6-(1-ethoxy-1,3-butadienyl)dihydropyran derivatives that undergo a Nazarov electrocyclic reaction under mild acidic conditions to give functionalized spirocyclic ketones. The product distribution and the stereoselectivity of the process are

  [反应：参见文本]α-乙氧基二烯基硼酸酯与内酯衍生的乙烯基三氟甲磺酸酯之间的Suzuki-Miyaura交叉偶联反应提供了功能化的6-（1-乙氧基-1,3-丁二烯基）二氢吡喃衍生物，该衍生物在温和的条件下进行了Nazarov环化反应在酸性条件下得到官能化的螺环酮。该方法的产物分布和立体选择性强烈取决于α-乙氧基二烯和二氢吡喃部分的取代。在二氢吡喃部分上存在C 2-取代基时，观察到高的立体选择性。根据过渡态的几何形状解释了结果。
• Remote Stereocontrol in the Nazarov Reaction:  A New Approach to the Core of Roseophilin
  作者：Ernesto G. Occhiato、Cristina Prandi、Alessandro Ferrali、Antonio Guarna

  DOI：10.1021/jo0504058

  日期：2005.5.1

  Three different procedures are compared to obtain properly substituted divinyl ketones in which one of the double bonds is embedded in a five-membered heterocyclic structure and therefore suitable to produce cyclopenta-fused pyrrole derivatives by the acid-catalyzed Nazarov reaction. These, on treatment with TFA, afforded 2,4-cis-disubstituted 2,3,4,5-tetrahydro-1H-cyclopenta[b]pyrrol-6-ones with high stereocontrol. One of these Nazarov products was oxidized to the corresponding 4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one derivative, thus obtaining an enantiopure key intermediate in the total synthesis of roseophilin.
• BESTMANN, H. J.;ROTH, K.;ETTLINGER, M., CHEM. BER., 1982, 115, N 1, 161-171
  作者：BESTMANN, H. J.、ROTH, K.、ETTLINGER, M.

  DOI：——

  日期：——