methyl 2-(((2-ethoxy-2-oxoethyl)thio)(phenyl)methyl)acrylate | 1198565-26-2

• 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: methyl 2-(((2-ethoxy-2-oxoethyl)thio)(phenyl)methyl)acrylate
• CAS: 1198565-26-2
• 化学式: C₁₅H₁₈O₄S
• 分子量: 294.372
• InChiKey: UPVLPVWLFNPRDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(((2-ethoxy-2-oxoethyl)thio)(phenyl)methyl)acrylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80 %的产率得到
  参考文献：
  名称：

  Mechanism‐Guided Design of Chain‐Growth Click Polymerization Based on a Thiol‐Michael Reaction

  摘要：

  AbstractThe development of chain‐growth click polymerization is challenging yet desirable in modern polymer chemistry. In this work, we reported a novel chain‐growth click polymerization based on the thiol‐Michael reaction. This polymerization could be performed efficiently under ambient conditions and spatiotemporally regulated by ultraviolet light, allowing the synthesis of sulfur‐containing polymers in excellent yields and high molecular weights. Density functional theory calculations indicated that the thiolate addition to the Michael acceptor is the rate‐determining step, and introducing the phenyl group could facilitate the chain‐growth process. This polymerization is a new type of chain‐growth click polymerization, which will provide a unique approach to creating functional polymers.

  DOI：

  10.1002/anie.202217895
• 作为产物：
  描述：

  苯甲醛 在 三乙烯二胺 作用下， 以 四氢呋喃 为溶剂， 反应 36.67h， 生成 methyl 2-(((2-ethoxy-2-oxoethyl)thio)(phenyl)methyl)acrylate
  参考文献：
  名称：

  Mechanism‐Guided Design of Chain‐Growth Click Polymerization Based on a Thiol‐Michael Reaction

  摘要：

  AbstractThe development of chain‐growth click polymerization is challenging yet desirable in modern polymer chemistry. In this work, we reported a novel chain‐growth click polymerization based on the thiol‐Michael reaction. This polymerization could be performed efficiently under ambient conditions and spatiotemporally regulated by ultraviolet light, allowing the synthesis of sulfur‐containing polymers in excellent yields and high molecular weights. Density functional theory calculations indicated that the thiolate addition to the Michael acceptor is the rate‐determining step, and introducing the phenyl group could facilitate the chain‐growth process. This polymerization is a new type of chain‐growth click polymerization, which will provide a unique approach to creating functional polymers.

  DOI：

  10.1002/anie.202217895

文献信息

• Regioselective synthesis of poly-substituted thiophenes from Baylis–Hillman adducts
  作者：Hyun Seung Lee、Se Hee Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2009.09.012

  日期：2009.11

  The reaction of Baylis–Hillman acetates and ethyl mercaptoacetate in the presence of DBU in DMF produced 2,3,4-trisubstituted tetrahydrothiophenes at room temperature as a diastereomeric mixture via the sequential SN2′ and Michael addition. Aromatization of tetrahydrothiophenes by DDQ oxidation produced 2,3,4-trisubstituted thiophenes in good yields.

  在DBU中，在DBU中，Baylis–Hillman乙酸盐和巯基乙酸乙酯的反应通过连续的S N 2'和Michael加成反应，在室温下生成2,3,4-三取代的四氢噻吩，为非对映异构体混合物。通过DDQ氧化对四氢噻吩进行芳香化处理，可得到高产率的2,3,4-三取代噻吩。