(1Z,3E)-1,4-diphenyl-1-methyl-1,3-butadiene | 40391-41-1

• 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: (1Z,3E)-1,4-diphenyl-1-methyl-1,3-butadiene
• 英文别名: penta-1,3-diene-1,4-diyldibenzene；1,4-Diphenyl-1,3-pentadiene；[(1E,3Z)-4-phenylpenta-1,3-dienyl]benzene
• CAS: 40391-41-1
• 化学式: C₁₇H₁₆
• 分子量: 220.314
• InChiKey: KIHWPIBJULXNGT-VQDQISGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-(1-phenylethyl)-1H-benzo[d][1,2,3]triazole 在 正丁基锂 、 四氯化钛 、 铜 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 15.0h， 生成 (1Z,3E)-1,4-diphenyl-1-methyl-1,3-butadiene
  参考文献：
  名称：

  Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation

  摘要：

  Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton alpha to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and alpha,beta-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(beta-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a-j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.

  DOI：

  10.1021/jo980616v

文献信息

• Site-Selective and Stereoselective <i>trans</i>-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine–Pd Complex
  作者：Senmiao Xu、Yuanzhe Zhang、Bo Li、Shih-Yuan Liu

  DOI：10.1021/jacs.6b09759

  日期：2016.11.9

  A concise synthesis of monobenzofused 1,4-azaborine phosphine ligands (Senphos) is described. These Senphos ligands uniquely support Pd-catalyzed trans-selective hydroboration of terminal and internal 1,3-enynes to furnish corresponding dienylboronates in high efficiency and diastereoselectivity. X-ray structural analysis of the Senphos-Pd(0) complex reveals a κ2-P-η2-BC coordination mode, and this

  描述了单苯并稠合 1,4-氮杂硼膦配体 (Senphos) 的简明合成。这些 Senphos 配体独特地支持 Pd 催化的末端和内部 1,3-烯炔的反式选择性硼氢化反应，以高效和非对映选择性提供相应的二烯基硼酸酯。Senphos-Pd(0) 配合物的 X 射线结构分析揭示了 κ2-P-η2-BC 配位模式，并且这种分离的配合物已被证明可作为反式硼氢化反应的有效催化剂。这项工作表明，BN/CC 等排方法提供的扩展化学空间转化为立体选择性催化转化背景下的功能空间。
• Hemilabile P,N-Ligand-Assisted Gold-Catalyzed Heck Reaction of Aryl and Styryl Iodides with Styrenes
  作者：Cunbo Wei、Lizhu Zhang、Zhonghua Xia

  DOI：10.1021/acs.orglett.3c02244

  日期：2023.9.22

  Heck reaction of aryl and styryl iodides with styrenes was developed. The hemilabile P,N-ligand-assisted gold-catalyzed C(sp2)–C(sp2) cross-coupling can synthesize stilbenes and bistyryl complexes, with good functional-group tolerance and mild conditions. The elementary organometallic steps of migratory insertion and β-hydride elimination might be involved in this ligand-enabled Au(I)/Au(III)-catalyzed

  开发了金催化的芳基碘化物和苯乙烯基碘化物与苯乙烯的 Heck 反应。半不稳定的P,N-配体辅助金催化的C(sp 2 )–C(sp 2 )交叉偶联可以合成茋和联苯乙烯配合物，具有良好的官能团耐受性和温和的条件。迁移插入和 β-氢化物消除的基本有机金属步骤可能涉及这种配体启用的 Au(I)/Au(III) 催化的与苯乙烯的 Heck 反应。
• Ag+-catalyzed rearrangements. XIV. Influence of structural features of the course of bicyclo[1.1.0]butane rearrangements catalyzed by silver(I) ion
  作者：Leo A. Paquette、Richard P. Henzel、Stanley E. Wilson

  DOI：10.1021/ja00777a021

  日期：1972.11
• Iron-Promoted Elimination of β-Thioalkoxy Alcohols. Olefination by Coupling of a Carbonyl Group with a Dithioacetal
  作者：Li-Fu Huang、Chih-Wei Chen、Tien-Yau Luh

  DOI：10.1021/ol701579f

  日期：2007.8.1

  Treatment of propargylic dithiolanes with (BuLi)-Bu-n followed by a carbonyl electrophile yields the corresponding propargylic dithioacetals. Upon treatment with 1 equiv of Fe(acac)(3) and excess MeMgI, elimination of SR and OH moieties from 8 affords the corresponding olefins in satisfactory yield. Benzylic dithioacetals behave similarly. The reaction can be considered an alternative of McMurry coupling of two different carbonyl equivalents.
• Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation
  作者：Alan R. Katritzky、Dai Cheng、Scott A. Henderson、Jianqing Li

  DOI：10.1021/jo980616v

  日期：1998.9.1

  Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton alpha to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and alpha,beta-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(beta-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a-j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.