hex-1-ene-1,1,2-triyltribenzene | 69052-92-2

• 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: hex-1-ene-1,1,2-triyltribenzene
• 英文别名: 1,1,2-triphenyl-1-hexene；1,1,2-triphenyl-hex-1-ene；1,1,2-Triphenyl-hex-1-en；1,1,2-Triphenylhex-2-en；1,1-Diphenylhex-1-en-2-ylbenzene
• CAS: 69052-92-2
• 化学式: C₂₄H₂₄
• 分子量: 312.455
• InChiKey: KZLZPWSBYMOFQV-UHFFFAOYSA-N

物化性质

• 熔点：
  90-92 °C
• 沸点：
  412.3±25.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  cis-1,2-diphenyloxirane 在 正丁基锂 、 四甲基乙二胺 、 叔丁基锂 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 正戊烷 为溶剂， 反应 0.75h， 生成 hex-1-ene-1,1,2-triyltribenzene
  参考文献：
  名称：

  通过将锂化的环氧化合物插入硼酸酯中来迭代合成烯烃。

  摘要：

  锂化的环氧化物的插入硼酸酯，随后通过热合成在剔除提供立体有择的条目为烯烃。该过程避免了过渡金属，并且易于迭代以提供更高的取代模式。

  DOI：

  10.1021/acs.orglett.9b00517

文献信息

• Tetrasubstituted Olefin Synthesis via Pd-Catalyzed Addition of Arylboronic Acids to Internal Alkynes Using O₂ as an Oxidant
  作者：Chengxiang Zhou、Richard C. Larock

  DOI：10.1021/jo060104d

  日期：2006.4.1

  alkynes provides a convenient route to a wide variety of tetrasubstituted olefins. The reaction is conducted in DMSO using molecular O2 as an oxidant in the absence of any base. The reaction involves the cis addition of two aryl groups from the arylboronic acid to opposite ends of the triple bond of the internal alkyne. The synthesis tolerates a wide variety of functional groups, including alcohol, aldehyde

  芳基硼酸和内部炔烃的Pd（II）催化反应为广泛的四取代烯烃提供了便捷的途径。该反应在不存在任何碱的情况下使用分子O 2作为氧化剂在DMSO中进行。该反应涉及从芳基硼酸顺式加成两个芳基至内部炔的三键的相对端。该合成可耐受多种官能团，包括醇，醛，酯，TMS和乙缩醛基团。富电子的二烷基乙炔（例如4-辛炔）以中等收率提供高度取代的1,3-二烯。通过芳基硼酸的均偶联，非常温和的O 2 / DMSO条件也提供了良好的佳收率的联芳基。
• Regio- and Stereoselective Route to Tetrasubstituted Olefins by the Palladium-Catalyzed Three-Component Coupling of Aryl Iodides, Internal Alkynes, and Arylboronic Acids
  作者：Chengxiang Zhou、Richard C. Larock

  DOI：10.1021/jo048265+

  日期：2005.5.1

  The Pd-catalyzed three-component coupling of readily available aryl iodides, internal alkynes, and arylboronic acids provides a convenient, one-step, regio- and stereoselective route to tetrasubstituted olefins in good to excellent yields, although electron-poor aryl iodides and dialkylalkynes normally afford only low yields under our standard reaction conditions. The proper combination of substrates

  易获得的芳基碘化物，内部炔烃和芳基硼酸的Pd催化三组分偶合提供了便捷，一步式，区域选择性和立体选择性的途径，以良好或优异的收率获得了四取代烯烃，尽管贫电子的芳基碘化物和二烷基炔烃通常在我们的标准反应条件下收率低。底物和反应条件的适当组合对于高收率很重要。水的存在通常显着增加所需四取代烯烃的产率。反应涉及顺式-将来自芳基碘化物的芳基加成至炔烃的受阻较少或更富电子的末端，而将来自芳基硼酸的芳基加至另一末端。还成功开发了一种改进的室温程序，该程序对某些基材非常有效。通过应用我们的合成方案，他莫昔芬及其衍生物以简洁，区域选择性和立体选择性的方式合成。
• Design and synthesis of acyclic triaryl (Z)-olefins: a novel class of cyclooxygenase-2 (COX-2) inhibitors
  作者：Md. Jashim Uddin、P.N. Praveen Rao、Edward E. Knaus

  DOI：10.1016/j.bmc.2004.08.021

  日期：2004.11

  A group of acyclic 2-alkyl-1, 1-diphenyl-2-(4-methylsulfonylphenyl)ethenes was designed for evaluation as selective cyclooxygenase-2 (COX-2) inhibitors. In vitro COX-1 and COX-2 isozyme inhibition structure-activity studies identified 1,1-diphenyl-2(4-methylsulfonylphenyl)hex-1-ene as a highly potent (IC50 = 0.014muM), and an extremely selective [COX-2 selectivity index (SI) >7142], COX-2 inhibitor that showed superior anti-inflammatory (A1) activity (ID50 = 2.5 mg/kg) relative to celecoxib (ID50 = 10.8mg/kg). This initial study was extended to include the design of a structurally related group of acyclic triaryl (Z)-olefins possessing an acetoxy (OAc) substituent at the para-position of the C-1 phenyl ring that is cis to a C-2 4-methylsulfonylphenyl substituent. COX-1 and COX-2 inhibition studies showed that (Z)-1-(4-acetoxyphenyl)-1-phenyl-2-(4-methylsulfonylphenyl)but-1-ene [(Z)-13b] is a potent (COX-1 IC50 = 2.4muM; COX-2 IC50 = 0.03 muM), and selective (COX-2 SI = 81), COX-2 inhibitor which is a potent AI agent (ID50 = 4.1 mg/kg) with equipotent analgesic activity to celecoxib. A molecular modeling (docking) study showed that the SO2Me substituent of (Z)-13b inserts deep inside the 2degrees-pocket of the COX-2 active site where one of the O-atoms of SO, group undergoes a H-bonding interaction with Phe(518). The p-OAc substituent on the C-1 phenyl ring is oriented in a hydrophobic pocket comprised of Met(522), Gly(526), Trp(387), Tyr(348), and Tyr(385), and the C-2 ethyl substituent is oriented towards the mouth of the COX-2 channel in the vicinity of amino acid residues Arg(12)0, Leu(531), and Val(349). Structure-activity data acquired indicate that a (Z)olefin having cis C-1 4-acetoxyphenyl (phenyl) and C-2 4-methylsulfonylphenyl substituents, and a C-1 phenyl substituent in conjunction with either a C-2 hydrogen or short alkyl substituent provides a novel template to design acyclic olefinic COX-2 inhibitors that, like aspirin, have the potential to acetylate COX-2. (C) 2004 Elsevier Ltd. All rights reserved.
• Alkylations of Mono- and Dipotassio-2,3,3-triphenylpropionitrile. Equilibrium Factor in Benzhydrylations of 1,2-Dianions. Dehydrocyanation¹
  作者：William G. Kofron、William R. Dunnavant、Charles R. Hauser

  DOI：10.1021/jo01055a008

  日期：1962.8
• Melamed,U.; Feit,B.A., Journal of the Chemical Society. Perkin transactions I, 1978, p. 1228 - 1232
  作者：Melamed,U.、Feit,B.A.

  DOI：——

  日期：——