(E)-1-methyl-4-(4-(trifluoromethyl)styryl)benzene | 143958-88-7

• 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: (E)-1-methyl-4-(4-(trifluoromethyl)styryl)benzene
• 英文别名: 4-(trifluoromethyl)-4'-methyl-trans-stilbene；(E)-4-methyl-4'-(trifluoromethyl)stilbene；(E)-4-trifluoromethyl-4'-methylstilbene；4-Methyl-4'-(trifluoromethyl)stilbene；1-methyl-4-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]benzene
• CAS: 143958-88-7
• 化学式: C₁₆H₁₃F₃
• 分子量: 262.274
• InChiKey: UJIYIFQKSLDDIR-VOTSOKGWSA-N

物化性质

• 沸点：
  311.9±37.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-methyl-4-(4-(trifluoromethyl)styryl)benzene 在 sodium hydroxide 、 叠氮磷酸二苯酯 、 sodium methylate 、 乙酸酐 、 copper(II) sulfate 、 溶剂黄146 、 三乙胺 、 sodium nitrite 作用下， 以 甲醇 、 甲苯 、 苯 为溶剂， 反应 10.55h， 生成 1-p-Trifluormethylphenyl-3-p-tolylallen
  参考文献：
  名称：

  Electron demand in the transition state of the cyclopropylidene to allene ring opening

  摘要：

  The electronic structure of the transition state for the cyclopropylidene to allene conversion has been probed. The methodology involved the relative rates of ring opening vs trapping by MeOH for a series of variously substituted 2,3-diarylcyclopropylidenes. With the assumption that the rate of trapping was unaffected by substituents, a Hammett correlation was constructed. The negative value (-0.72) for rho indicated that the carbenic center attracts electron density in the ring-opening transition state, much like the cyclopropyl cation to allyl cation transition state. Temperature-dependent studies showed that the observed preference for ring opening was driven by entropy factors. Also, using reasonable estimates for the close to diffusion-controlled trapping activation enthalpies, the derived enthalpies for ring opening were in close agreement with the best theoretical values.

  DOI：

  10.1021/jo00049a042
• 作为产物：
  描述：

  1-methyl-4-((4-(trifluoromethyl)phenyl)ethynyl)benzene 在 sodiumsulfide nonahydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以52%的产率得到(E)-1-methyl-4-(4-(trifluoromethyl)styryl)benzene
  参考文献：
  名称：

  Transition-Metal-Free Semihydrogenation of Diarylalkynes: Highly Stereoselective Synthesis of trans-Alkenes Using Na₂S·9H₂O

  摘要：

  A highly stereoselective and efficient transition-metal-free semihydrogenation of internal alkynes to E-alkenes using cheap and green water as hydrogen donor is described. The reactions are conducted under convenient conditions and provide products in good to excellent yields, with broad substrate scope, including a variety of diarylalkynes.

  DOI：

  10.1021/ol501137x

文献信息

• Direct Wittig Olefination of Alcohols
  作者：Qiang-Qiang Li、Zaher Shah、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/acs.joc.7b02720

  日期：2018.1.5

  A base-promoted transition metal-free approach to substituted alkenes using alcohols under aerobic conditions using air as the inexpensive and clean oxidant is described. Aldehydes are relatively difficult to handle compared to corresponding alcohols due to their volatility and penchant to polymerize and autoxidize. Wittig ylides are easily oxidized to aldehydes and consequently form homo-olefination

  描述了在有氧条件下使用醇作为廉价且清洁的氧化剂，使用醇在碱性条件下使用无醇过渡醇取代烯烃的方法。与相应的醇相比，由于醛的挥发性和聚合和自氧化倾向，因此醛相对较难处理。维蒂希酸根易于氧化成醛，因此形成均烯烃化产物。首次通过同时原位生成乙叉和乙叉的策略，无需预先制备醛或乙叉醇就将醇直接转移到烯烃中。因此，实现了二醇的二/单可控烯烃化。这种合成实用的方法已用于克级合成的药物，如DMU-212和白藜芦醇。
• 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
• Diarylrhodates as Promising Active Catalysts for the Arylation of Vinyl Ethers with Grignard Reagents
  作者：Takanori Iwasaki、Yoshinori Miyata、Ryo Akimoto、Yuuki Fujii、Hitoshi Kuniyasu、Nobuaki Kambe

  DOI：10.1021/ja5043534

  日期：2014.7.2

  with 2 equiv of aryl Grignard reagents, were found to be effective active catalysts in cross-coupling reactions of vinyl ethers with aryl Grignard reagents, giving rise to the production of vinyl arenes. In this catalytic system, vinyl-O bonds were preferably cleaved over Ar-O or Ar-Br bonds. A lithium rhodate complex was isolated, and its crystal structure was determined by X-ray crystallography.

  通过 [RhCl(cod)]2 与 2 当量的芳基格氏试剂反应生成的阴离子二芳基铑配合物被发现是乙烯基醚与芳基格氏试剂交叉偶联反应的有效活性催化剂，从而产生乙烯基芳烃. 在该催化系统中，乙烯基-O键优选在Ar-O或Ar-Br键上裂解。分离出一种铑酸锂络合物，并通过 X 射线晶体学确定其晶体结构。
• [EN] HETEROCYCLIC MITOCHONDRIAL ACTIVITY INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS HÉTÉROCYCLIQUES DE L'ACTIVITÉ MITOCHONDRIALE ET UTILISATIONS ASSOCIÉES
  申请人：UNIV MONTREAL

  公开号：WO2019084662A1

  公开（公告）日：2019-05-09

  Heterocyclic compounds of Formula (I) and pharmaceutically acceptable salt thereof are disclosed. The use of such heterocyclic compounds and pharmaceutically acceptable salt thereof for the treatment of cancers, and more particularly cancers sensitive to mitochondrial activity inhibition and increased reactive oxygen species (ROS) levels, is also disclosed. Such cancers include acute myeloid leukemia (AML), preferably AML characterized by certain features, such as high level of expression of one or more Homeobox (HOX)-network genes, high and/or low expression of specific genes, the presence of one or more cytogenetic or molecular risk factors such as intermediate cytogenetic risk, Normal Karyotype (A/K), mutated NPM1, mutated CEBPA, mutated FLT3, mutated DNMT3A, mutated TET2, mutated IDH1, mutated IDH2, mutated RUNX1, mutated WT1, mutated SRSF2, intermediate cytogenetic risk with abnormal karyotype (intern(abnK)), trisomy 8 (+8) and/or abnormal chromosome (5/7), and/or a high leukemic stem cell (LSC) frequency.

  化合物的分子式（I）的杂环化合物及其药用盐已被披露。还披露了这种杂环化合物及其药用盐用于治疗癌症，尤其是对于对线粒体活性抑制和增加活性氧化物（ROS）水平敏感的癌症。这些癌症包括急性髓样白血病（AML），最好是具有某些特征的AML，例如高水平表达一个或多个Homeobox（HOX）网络基因，特定基因的高和/或低表达，存在一个或多个细胞遗传学或分子风险因素，如中等细胞遗传学风险，正常核型（A/K），突变NPM1，突变CEBPA，突变FLT3，突变DNMT3A，突变TET2，突变IDH1，突变IDH2，突变RUNX1，突变WT1，突变SRSF2，具有异常核型的中等细胞遗传学风险（intern(abnK)），三体8（+8）和/或异常染色体（5/7），和/或高白血病干细胞（LSC）频率。
• Metal–Micelle Cooperativity: Phosphine Ligand-Free Ultrasmall Palladium(II) Nanoparticles for Oxidative Mizoroki–Heck-type Couplings in Water at Room Temperature
  作者：Tharique N. Ansari、Jacek B. Jasinski、David K. Leahy、Sachin Handa

  DOI：10.1021/jacsau.0c00087

  日期：2021.3.22

  stems from metal cation−π interactions of the styrene along with transmetalation by the arylboronic acid, followed by insertion and β-H elimination to furnish the coupled product along with the reoxidation of Pd by benzoquinone to complete the catalytic cycle. This method is very mild and sustainable, both in terms of NP synthesis and subsequent catalysis, and shows broad substrate scope while circumventing

  两亲物 PS-750-M 从 Pd(OAc) 2 中生成稳定的、无膦配体且具有催化活性的超小 Pd(II) 纳米粒子 (NPs)，防止它们的沉淀、聚合和氧化态变化。PS-750-M 直接与 Pd(II) NP 表面相互作用，高分辨率质谱和红外光谱证实了它们的高稳定性。NPs 中的 Pd 阳离子很可能被氢氧化物和乙酸根离子结合在一起。纳米颗粒通过 HRTEM 表征，揭示它们的形态和粒度分布，通过 HRMS 和 IR 表征，为 NP-两亲相互作用提供证据。在室温下在水中氧化 Mizoroki-Heck 型偶联的背景下检查了 NP 催化活性。热过滤、热萃取和三相测试表明在胶束界面发生多相催化，而不是在溶液中发生均相催化。NMR研究表明，催化活性源于苯乙烯的金属阳离子-π相互作用以及芳基硼酸的金属转移，然后插入和β-H消除以提供偶联产物以及苯醌对Pd的再氧化以完成催化循环。这种方法在 NP 合成和