ethyl 4-(5-methylthiophen-2-yl)-2-oxobut-3-enoate | 1000400-80-5

• 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 4-(5-methylthiophen-2-yl)-2-oxobut-3-enoate
• CAS: 1000400-80-5
• 化学式: C₁₁H₁₂O₃S
• 分子量: 224.28
• InChiKey: XKQUVAKCWNZCRS-UHFFFAOYSA-N

物化性质

• 熔点：
  42-43 °C(Solvent: Diisopropyl ether)
• 沸点：
  338.4±34.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  吡唑 、 ethyl 4-(5-methylthiophen-2-yl)-2-oxobut-3-enoate 以 二氯甲烷 为溶剂， 反应 24.0h， 以34%的产率得到ethyl 4-(5-methylthiophen-2-yl)-2-oxo-4-(1H-pyrazol-1-yl)butanoate
  参考文献：
  名称：

  Catalyst-free aza-Michael addition of azole to β,γ-unsaturated-α-keto ester: an efficient access to C–N bond formation

  摘要：

  An efficient aza-Michael addition of azoles to beta,gamma-unsaturated-alpha-keto esters under room temperature conditions has been developed. In this conjugate addition, no additional catalyst is employed. Azole reacts with beta,gamma-unsaturated-alpha-keto ester smoothly to afford new C-N bond adducts in good to excellent yields (up to 96%). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.132

文献信息

• Organocatalytic asymmetric Michael-type reaction between β,γ-unsaturated α-keto ester and α-nitro ketone
  作者：Pengfei Li、Sau Hing Chan、Albert S. C. Chan、Fuk Yee Kwong

  DOI：10.1039/c1ob06191g

  日期：——

  A Michael-type reaction of β,γ-unsaturated α-keto ester and α-nitro ketone was established. With a thiourea catalyst derived from cinchona alkaloid, the reactions afford products in 47–94% yields with 68–96% ee.

  建立了β，γ-不饱和α-酮酯与α-硝基酮的迈克尔型反应。用金鸡纳生物碱衍生的硫脲催化剂，反应可提供47-94％收率和68-96％ee的产物。
• Organocatalytic Asymmetric Aldol Reaction of Ketones with β,γ-Unsaturated α-Keto Esters: An Efficient Access to Chiral Tertiary Alcohol Skeletons
  作者：Pengfei Li、Sau Hing Chan、Albert S. C. Chan、Fuk Yee Kwong

  DOI：10.1002/adsc.201000982

  日期：2011.5.9

  organocatalytic aldol reaction of ketones and β,γ‐unsaturated α‐keto esters for constructing the chiral tertiary alcohol motif. With the application of 9‐amino(9‐deoxy)epi‐Cinchona alkaloid and an acidic additive as catalysts, both acyclic and cyclic ketones react with β,γ‐unsaturated α‐keto esters smoothly to afford aldol adducts in good to excellent yields and asymmetric induction. This protocol offers a new

  此更新描述了酮和β，γ-不饱和α-酮酸酯的高效有机催化羟醛反应，可用于构建手性叔醇基序。通过使用9-氨基（9-脱氧）表金鸡纳生物碱和酸性添加剂作为催化剂，无环和环状酮均能与β，γ-不饱和α-酮酸酯平稳地反应，从而以良好的收率和良好的收率获得醛醇加合物。不对称感应。该方案为构建相邻的手性碳中心和合成手性β-羟基羰基化合物提供了一条新途径。