(E)-3-[2-(4-methylphenyl)ethenyl]thiophene | 190520-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-[2-(4-methylphenyl)ethenyl]thiophene
• 英文别名: (E)-3-(4-methylstyryl)thiophene；3-[(E)-2-(4-methylphenyl)ethenyl]thiophene
• CAS: 190520-82-2
• 化学式: C₁₃H₁₂S
• 分子量: 200.304
• InChiKey: COFNKNQHFNGMPF-VOTSOKGWSA-N

物化性质

• 沸点：
  312.7±22.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-3-[2-(4-methylphenyl)ethenyl]thiophene 以42%的产率得到
  参考文献：
  名称：

  TEDJAMULIA, M. L.;STUART, J. G.;TOMINAGA, YOSHINORI;CASTLE, R. N.;LEE, M.+, J. HETEROCYCL. CHEM., 1984, 21, N 4, 1215-1219

  摘要：

  DOI：
• 作为产物：
  描述：

  3-噻吩甲醛 、 4-甲基苄基膦酸二乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-3-[2-(4-methylphenyl)ethenyl]thiophene
  参考文献：
  名称：

  Amide bond surrogates: A study in thiophenesulfonamide based endothelin receptor antagonists

  摘要：

  The potential proteolytic instability of the amide bond present in some ETA selective thiophenesulfonamide endothelin antagonists exemplified by TBC-10708 led us to investigate the replacement of this moiety with stable amide bond surrogates such as a trans double bond and an ethylene spacer. The effect of these replacements on the binding affinity is described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00133-9

文献信息

• Synthesis of Deuterated (<i>E</i>)-Alkene through Xanthate-Mediated Hydrogen–Deuterium Exchange Reactions
  作者：Jiaming Li、Jian Li、Xiaoliang Ji、Runfa He、Yang Liu、Zebin Chen、Yubing Huang、Qiang Liu、Yibiao Li

  DOI：10.1021/acs.orglett.1c02600

  日期：2021.10.1

  Herein we have developed a reversible hydrogen–deuterium exchange reaction of nonactivated olefins. By using EtOCS2K as a mediator, the H/D exchange reaction was realized through repeated addition and elimination reactions, demonstrating reversible H/D exchange between ordinary olefins and deuterated olefins. Using the lowest cost D2O without precious metal catalysts and ligands, a broad spectrum of

  在此，我们开发了非活化烯烃的可逆氢-氘交换反应。以EtOCS 2 K为介体，通过反复加成和消去反应实现H/D交换反应，证明了普通烯烃和氘化烯烃之间的H/D交换是可逆的。在没有贵金属催化剂和配体的情况下使用最低成本的 D 2 O，实现了广泛的官能团兼容性。
• Palladium(<scp>ii</scp>) ligated with a selenated (Se, C_NHC, N⁻)-type pincer ligand: an efficient catalyst for Mizoroki–Heck and Suzuki–Miyaura coupling in water
  作者：Kamal Nayan Sharma、Naveen Satrawala、Avinash Kumar Srivastava、Munsaf Ali、Raj Kumar Joshi

  DOI：10.1039/c9ob01674k

  日期：——

  respectively) at very low catalyst loading (0.2 mol%) and under mild reaction conditions in water. The complex (1) was also investigated for Suzuki-Miyaura coupling and found to be selectively efficient (yields up to 94%) for Suzuki-Miyaura coupling of aromatic bromides at 0.01 mol% of 1 in water. All coupling reactions were carried out in the green and economical solvent, water, which is highly desirable

  新型的1- [N-苄基乙酰胺基] -3- [1-（2-苯基硒烯基乙基）]苯并咪唑鎓氯化物（L）是一种新型（Se，CNHC，N-）型钳位配体（L）的前体。 1H-苯并咪唑与二氯化乙烯，硒酚钠和N-苄基-2-氯乙酰胺的一系列连续反应可实现高收率。L与PdCl2的钯促进反应生成了对水分和空气不敏感的络合物[Pd（L-H2Cl）Cl]（1），证明了芳族溴化物和氯化物的Mizoroki-Heck偶联具有出色的催化潜力（收率较高）。在极低的催化剂负载量（0.2摩尔％）和温和的反应条件下，在水中分别可高达94％和70％）。还研究了络合物（1）的Suzuki-Miyaura偶联，发现在水中0.01 mol％的芳香族溴化物的Suzuki-Miyaura偶联中选择性有效（产率高达94％）。所有偶联反应均在绿色经济的溶剂水中进行，这对于工业中复杂分子的批量合成是非常需要的。在催化过程中，复合物1原位转化为PdSe纳米颗粒（NP，尺寸范围5-6
• Nickel-Catalyzed System for the Cross-Coupling of Alkenyl Methyl Ethers with Grignard Reagents under Mild Conditions
  作者：Thomas Hostier、Zeina Neouchy、Vincent Ferey、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1021/acs.orglett.8b00313

  日期：2018.4.6

  A nickel-catalyzed cross-coupling of alkenyl methyl ethers with Grignard reagents, under mild conditions, is described. These conditions allowed access to various stilbenes and heterocyclic stilbenic derivatives as well as to a potential anticancer agent DMU-212.

  描述了在温和条件下镍催化的链烯基甲基醚与格利雅试剂的交叉偶联。这些条件允许获得各种斯蒂芬烯和杂环斯蒂芬烯衍生物以及潜在的抗癌剂DMU-212。
• Determining the excited-state substituent constants of furyl and thienyl groups
  作者：Junyan Qu、Chao-Tun Cao、Chenzhong Cao

  DOI：10.1002/poc.3799

  日期：2018.5

  and their wavelength of absorption maximum λmax was recorded. For the wavenumber νmax (cm−1, νmax = 1/λmax) of the obtained λmax, a quantitative correlation analysis was performed, and 6 excited‐state substituent constants of groups X were obtained by means of curve‐fitting method. Taking the νmax values of total 90 compounds of styrene derivatives as a data set (including 25 compounds from reference

  合成了六个包含苯乙烯母体分子骨架的系列苯乙烯衍生物XCH═CHArY（共65个）（其中Y为OMe，Me，H，F，Cl，CF 3，CN和NO 2，X为2-呋喃基，3-呋喃基，2'-甲基-2-呋喃基，2-噻吩基，3-噻吩基和2'-甲基-2-噻吩基）。在无水乙醇中测量其紫外线吸收光谱，并记录其最大吸收波长λmax。对于波数ν最大值（厘米-1，ν最大 = 1 /λ最大值所获得的λ的）最大，进行定量相关性分析，和6激发态取代基常数X组通过曲线拟合法获得。服用ν最大苯乙烯衍生物作为一个数据集（包括来自参考25个的化合物和该工作的65个的化合物）的总90种化合物的值，进行定量相关性分析，将所得的可靠性进行了验证。另外，双取代的席夫碱的12个样品（XCH═NArY）涉及上述基团X，合成，和它们的ν最大记录值。使用这些12 ν最大值与14个一起ν最大的从参考（总共26种化合物的）拍摄的席夫碱值，它被进一步验证了
• A comparative study on photosensitized oxidation of trans -2-vinylthiophenes with trans -3-vinylthiophenes
  作者：Kai Song、Ming-Li Peng、Ming Xu、Li-Zhu Wu、Li-Ping Zhang、Chen-Ho Tung

  DOI：10.1016/s0040-4039(02)01445-4

  日期：2002.9

  The photosensitized oxidation of trans-2-styrylthiophenes (trans-2-ST). trans-3-styrylthiophenes (trans-3-ST) and trans-1,2-di(2-thienyl)ethylene (trans-2-TE) were investigated using the sensitizers tetraplenylporphyrin (TPP) in a non-polar solvent and 9, 10-dicyanoanthracene (DCA) in a polar solvent. The oxidation pathway is dependent on the position of the vinyl substituent in the thiophene ring. While trans-2-ST and trans-2-TE only undergo photooxidation via the singlet oxygen pathway to yield [4+2] and [2+2] products, the photosensitized oxidation of trans-3-ST proceeds exclusively via the superoxide anion pathway to produce the thiophenecarboxaldehyde and benzaldehydes. All of the above substrates May undergo auto-photooxidation via a charge-transfer complex of the substrate and oxygen. (C) 2002 Published by Elsevier Science Ltd.