methyl (E)-4-(4-(tert-butyl)styryl)benzoate | 102405-30-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl (E)-4-(4-(tert-butyl)styryl)benzoate
• 英文别名: Methyl e-4-(2-(4-t-butylphenyl)ethen-1-yl)benzoate；methyl 4-[(E)-2-(4-tert-butylphenyl)ethenyl]benzoate
• CAS: 102405-30-1
• 化学式: C₂₀H₂₂O₂
• 分子量: 294.393
• InChiKey: IUULZQGCOHJESL-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (E)-4-(4-(tert-butyl)styryl)benzoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (E)-4-(4-叔丁基苯乙烯基)苯甲酸
  参考文献：
  名称：

  Retinobenzoic acids. 3. Structure-activity relationships of retinoidal azobenzene-4-carboxylic acids and stilbene-4-carboxylic acids

  摘要：

  Alkyl-substituted azobenzene-4-carboxylic acids are potent differentiation inducers of human promyelocytic leukemia cell line HL-60 to mature granulocytes. Their structure-activity relationships are very similar to those of other retinoidal benzoic acids which are generally represented by 4 and named retinobenzoic acids. The structure-activity relationships of azobenzenecarboxylic acids can also be applied to the known retinoid TTNPB (3). Thus, (E)-4-[2-(3,4-diisopropylphenyl)-1-propenyl]benzoic acid (St30 (28] and (E)-4-[2-(3-tert-butylphenyl)ethenyl]benzoic acid (St40 (29], the acyclic alkyl analogues of TTNPB, are nearly as active as retinoic acid. Among the oxidatively derived compounds (Az90, Ep series and Ox series) of azobenzene- or stilbenecarboxylic acids, Az90 (71) and Ep80 (61) have strong activities. However, all the bishydroxylated derivatives of TTNPB are inactive, while a diketo analogue Ox580 (69) has only weak potency. The activities of conformationally restricted compounds of TTNPB offer some information on the stereochemistry of the active form of these retinoidal compounds.

  DOI：

  10.1021/jm00125a027
• 作为产物：
  描述：

  4-叔丁基苯硼酸 在 水 、 copper diacetate 、 palladium diacetate 、 nickel diacetate 、 碳酸氢钠 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 20.0h， 生成 methyl (E)-4-(4-(tert-butyl)styryl)benzoate
  参考文献：
  名称：

  钯催化的有机苯乙烯与苯乙烯的交叉偶联得到不对称的 (E)-二苯乙烯和 (1E,3E)-1,4-Diarylbuta-1,3-二烯以及产物的荧光特性

  摘要：

  公开了一种通用且有效的钯催化的有机锑与苯乙烯的交叉偶联，以得到 ( E )-烯烃。通过使用有机锑试剂，该方法可以以良好的收率和高E / Z制备不对称的 ( E )-1,2-二芳基乙烯和 (1 E ,3 E )-1,4-二芳基丁二烯-1,3-二烯选择性和良好的官能团耐受性。白藜芦醇和 DMU-212 以高产率合成。该协议可以扩展到 (1 E ,3 E ,5 E )-1,6-diphenylhexa-1,3,5-triene的合成,产率为 40%。产品5e、5f和7a 显示出良好的光致发光量子产率，范围为 72% 至 99%。

  DOI：

  10.1021/acs.orglett.1c01532

文献信息

• Rhodium-catalyzed oxidative decarbonylative Heck-type coupling of aromatic aldehydes with terminal alkenes
  作者：Lei Kang、Feng Zhang、Lin-Ting Ding、Luo Yang

  DOI：10.1039/c5ra21610a

  日期：——

  rhodium-catalyzed oxidative decarbonylative Heck-type coupling of aromatic aldehydes with terminal alkenes to afford 1,2-disubstituted alkenes with good regio- and E-selectivity is developed. This reaction employs readily available aromatic aldehydes as the aryl electrophile counterpart and relies on selected acyl chloride as the crucial additive to activate the rhodium catalyst precursor.

  开发了铑催化的芳族醛与末端烯烃的氧化脱羰基Heck型偶联，以提供具有良好区域和E选择性的1,2-二取代的烯烃。该反应采用容易获得的芳族醛作为芳基亲电子试剂，并依赖于选定的酰氯作为活化铑催化剂前体的关键添加剂。
• Earth‐Abundant Recyclable Magnetic Iron Oxide Nanoparticles for Green‐light Mediated C−H Arylation in Heterogeneous Phase
  作者：Tanumoy Mandal、Ashwin Chaturvedi、Aznur Azim、Rohan Maji、Suman De Sarkar

  DOI：10.1002/chem.202401617

  日期：2024.8.6

  A magnetically isolable iron oxide nanoparticles is introduced as an efficient heterogeneous photocatalyst for non‐directed C‒H arylation employing aryl diazonium salts as the aryl precursors. This first‐row transition metal‐based photocatalyst revealed versatile activities and is applicable to a wide range of substrates, demonstrating brilliant efficacy and superior recyclability. Detailed catalytic characterization describes the physical properties and redox behavior of the Fe‐catalyst. Adequate control experiments helped to establish the radical‐based mechanism for the C‒H arylation.