methyl (2E)-2-(4-chlorobenzylidene)-4-phenylbutanoate | 1026729-28-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: methyl (2E)-2-(4-chlorobenzylidene)-4-phenylbutanoate
• 英文别名: methyl 2-(4-chlorobenzylidene)-4-phenylbutanoate；methyl (2E)-2-[(4-chlorophenyl)methylidene]-4-phenylbutanoate
• CAS: 1026729-28-1
• 化学式: C₁₈H₁₇ClO₂
• 分子量: 300.785
• InChiKey: MWHDMUXVXLYORD-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl 3-acetoxy-3-(4-chlorophenyl)-2-methylenepropanoate 、 苄基碘 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到methyl (2E)-2-(4-chlorobenzylidene)-4-phenylbutanoate
  参考文献：
  名称：

  Titanocene(III) Chloride Mediated Radical-Induced Addition to Baylis−Hillman Adducts: Synthesis of (E)- and (Z)-Trisubstituted Alkenes and α-Methylene/Arylidene δ-Lactones

  摘要：

  Baylis-Hillman adduct underwent smooth radical-induced condensation with activated bromo compounds and epoxides using titanocene(III) chloride (CP2TiCl) as the radical generator. The reactions of activated bromo compounds with 3-acetoxy-2-methylene alkanoates provided (E)-alkenes exclusively, whereas similar reactions with 3-acetoxy-2-methylenealkanenitriles led to (Z)-alkenes as the major product. The reactions of epoxides with Baylis-Hillman adduct furnished alpha-methylene/arylidene-delta-lactones in good yield via addition followed by in situ lactonization.

  DOI：

  10.1021/jo800049p

文献信息

• The coupling of alkylboronic acids and esters with Baylis–Hillman derivatives by Lewis base/photoredox dual catalysis
  作者：Hongqiang Ye、He Zhao、Shujian Ren、Hongfeng Ye、Dongping Cheng、Xiaonian Li、Xiaoliang Xu

  DOI：10.1016/j.tetlet.2019.04.015

  日期：2019.5

  Utilizing Lewis base/photoredox dual catalysis, carbon radicals generated from either alkylboronic acids or esters were coupled with Baylis–Hillman derivatives under visible light irradiation. This protocol provides a mild and operationally simple method for the synthesis of a variety of α,β-unsaturated carbonyl compounds in a broad scope of the substrates. The mechanism of Lewis base activation and

  利用路易斯碱/光氧化还原双重催化，烷基硼酸或酯产生的碳自由基在可见光照射下与Baylis-Hillman衍生物偶联。该方案提供了一种温和且操作简单的方法，可在广泛的底物中合成各种α，β-不饱和羰基化合物。可能涉及路易斯碱活化和还原淬灭循环的机理。
• 可见光催化α,β-不饱和羧酸酯衍生物的合成方法
  申请人：浙江工业大学

  公开号：CN110668940A

  公开（公告）日：2020-01-10

  本发明公开了一种式(I)所示的α,β‑不饱和羧酸酯衍生物的合成方法，其特征在于：所述合成方法是：在反应溶剂中，以式(III)所示的汉斯酯化合物和式(II)所示的Baylis‑Hillman衍生物为原料，惰性气体或N2保护、可见光光照条件以及光催化剂作用下，于室温常压下充分搅拌反应，之后反应混合物经后处理得到式(I)所示的α,β‑不饱和羧酸酯衍生物；所述的光催化剂选自下列化合物：Eosin Y、Ir(ppy)3、[Ir(dFCF3ppy)2(dtbpy)]PF6、Rose Bengal；所述的反应溶剂选自下列一种或任意几种的组合：N‑甲基吡咯烷酮、四氢呋喃、N,N‑二甲基甲酰胺、二氯甲烷、乙腈、二甲基亚砜。本发明方法具有反应条件温和、易于操作、广泛的官能团耐受性、可见光催化剂使用量低、收率高等优点。
• Titanocene(III) Chloride Mediated Radical-Induced Addition to Baylis−Hillman Adducts: Synthesis of (<i>E</i>)- and (<i>Z</i>)-Trisubstituted Alkenes and α-Methylene/Arylidene δ-Lactones
  作者：Samir K. Mandal、Moumita Paira、Subhas C. Roy

  DOI：10.1021/jo800049p

  日期：2008.5.1

  Baylis-Hillman adduct underwent smooth radical-induced condensation with activated bromo compounds and epoxides using titanocene(III) chloride (CP2TiCl) as the radical generator. The reactions of activated bromo compounds with 3-acetoxy-2-methylene alkanoates provided (E)-alkenes exclusively, whereas similar reactions with 3-acetoxy-2-methylenealkanenitriles led to (Z)-alkenes as the major product. The reactions of epoxides with Baylis-Hillman adduct furnished alpha-methylene/arylidene-delta-lactones in good yield via addition followed by in situ lactonization.