ethyl 5-oxohexa-2,3-dienoate | 1312466-05-9

• 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: ethyl 5-oxohexa-2,3-dienoate
• 英文别名: ethyl 5-oxo-2,3-hexadienoate
• CAS: 1312466-05-9
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: KHSMMCSMVPHKLA-UHFFFAOYSA-N

物化性质

• 沸点：
  252.7±10.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-oxohexa-2,3-dienoate 在 potassium tert-butylate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 13.0h， 生成 cyclohexan-3,5-dione spiro-1,2'-(1',3'-dithiane)
  参考文献：
  名称：

  Asymmetric Total Syntheses of (−)-Variabilin and (−)-Glycinol

  摘要：

  Total syntheses of (-)-variabilin and (-)-glycinol have been accomplished, using the catalytic, asymmetric "Interrupted" Feist-Benary reaction (IFB) as the key transformation to introduce both stereogenic centers. A monoquinidine pyrimidinyl ether catalyst affords the IFB products In over 90% ee in both cases. Other key steps include an intramolecular Buohwald-Hartwig coupling and a nickel-catalyzed aryl tosylate reduction.

  DOI：

  10.1021/ol201332u
• 作为产物：
  描述：

  ethyl 5-hydroxy-2-hexynoate 在 silica gel-supported Jones reagent 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以100%的产率得到ethyl 5-oxohexa-2,3-dienoate
  参考文献：
  名称：

  Asymmetric Total Syntheses of (−)-Variabilin and (−)-Glycinol

  摘要：

  Total syntheses of (-)-variabilin and (-)-glycinol have been accomplished, using the catalytic, asymmetric "Interrupted" Feist-Benary reaction (IFB) as the key transformation to introduce both stereogenic centers. A monoquinidine pyrimidinyl ether catalyst affords the IFB products In over 90% ee in both cases. Other key steps include an intramolecular Buohwald-Hartwig coupling and a nickel-catalyzed aryl tosylate reduction.

  DOI：

  10.1021/ol201332u

文献信息

• Synthesis of 1,3-dioxo-substituted allenes via copper(I)-catalyzed coupling of α-oxo-alkynes and α-oxo-diazos by controlling the sequence of adding substrates
  作者：Chulong Liu、Yunxiang Weng、Xiaobao Zeng、Weiping Zheng、Xinyan Wang、Yuefei Hu

  DOI：10.1016/j.tetlet.2019.01.015

  日期：2019.2

  A novel direct synthesis of 1,3-dioxo-substituted allenes was developed by copper(I)-catalyzed coupling of α-oxo-alkynes and α-oxo-diazos. It was a sequence of adding substrates-controlled method and the desired products were synthesized chemoselectively by adding α-oxo-alkyne terminally.

  通过铜（I）催化α-氧代炔烃和α-氧代重氮偶合的偶联反应，开发了一种新的直接合成1,3-二氧代取代的丙二烯的方法。这是添加底物控制方法的顺序，并且通过末端添加α-氧代炔烃来化学选择性地合成所需的产物。