1,1-双-(4-甲基苯基)-1,3-丁二烯 | 93874-11-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 1,1-双-(4-甲基苯基)-1,3-丁二烯
• 英文名称: 4,4'-(buta-1,3-diene-1,1-diyl)bis(methylbenzene)
• 英文别名: 1,1-Bis-(4-methylphenyl)-buta-1,3-diene；1-methyl-4-[1-(4-methylphenyl)buta-1,3-dienyl]benzene
• CAS: 93874-11-4
• 化学式: C₁₈H₁₈
• 分子量: 234.341
• InChiKey: XKWGSXSZRDBDMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090

反应信息

• 作为反应物：
  描述：

  4-羟基-N-甲基-2-喹啉 、 1,1-双-(4-甲基苯基)-1,3-丁二烯 在 manganese(III) triacetate dihydrate 作用下， 以 溶剂黄146 为溶剂， 以71%的产率得到3,5-dihydro-2-[2,2-bis(4-methylphenyl)ethenyl]-5-methylfuro[3,2-c]quinolin-4(2H)-one
  参考文献：
  名称：

  Mn(III)-based reaction of alkenes with quinolinones. Formation of peroxyquinolinones and quinoline-related derivatives

  摘要：

  The reactions of 1,1-disubstituted alkenes with 4-hydroxyquinolin-2(1H)-ones under both Mn(III)-catalyzed aerobic oxidation conditions at room temperature and Mn(III)-mediated oxidation conditions at reflux temperature are described. The Mn(III)-catalyzed aerobic oxidation afforded bis(hydroperoxyethyl)quinolinones and azatrioxa[4.431propellanes, while the oxidation with Mn(OAc)(3)center dot 2H(2)O produced furo[3,2-c]quinolin-4-one analogues. The existence of a substituent at the 3-position of the 4-hydroxyquinolin-2(1H)-ones prevented a double reaction with the alkenes, and (endoperoxy)quinolinones and/or (hydroperoxyethyl)quinolinones were obtained under the Mn(III)-catalyzed aerobic conditions, while furo[3,2-c]quinolinone hemiacetals and vinylquinolinones were selectively produced under the Mn(III)-mediated oxidation conditions depending on the reaction temperature and times. Cyclic assembly of quinolinone-related 1,3-dicarbonyl compounds such as dihydropyridinones, pyranones, and dimedone derivatives was also examined under elevated temperature conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.013
• 作为产物：
  描述：

  4,4'-二甲基二苯甲酮 在 manganese(IV) oxide 、 potassium tert-butylate 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 1,1-双-(4-甲基苯基)-1,3-丁二烯
  参考文献：
  名称：

  可见光驱动的 1,3-二烯与有机卤化物和 CO2 的区域选择性碳羧化

  摘要：

  利用光将二氧化碳 (CO 2 ) 转化为增值精细化学品是一种有吸引力的合成策略。在此，我们报道了一种前所未有的可见光驱动的 1,3-二烯与 CO 2的区域选择性碳羧化反应。在温和条件下使用芳基卤化物和烷基卤化物以及低成本甲酸钾 (HCOOK) 来产生二氧化碳自由基阴离子，作为具有挑战性的有机卤化物还原的有效还原剂。用 1,1-二芳基取代的 1,3-二烯实现了高度的 3,4-区域选择性碳羧化，而用受阻较小的单芳基取代的 1,3-二烯获得了主要的 1,4-碳羧化产物。该协议提供了一种从容易获得的 1,3-二烯和具有 CO 2的有机卤化物中生产复杂 β、γ-不饱和羧酸的快速方法。

  DOI：

  10.1039/d2gc01256a

文献信息

• Pd(0)-catalyzed cross-coupling of allyl halides with α-diazocarbonyl compounds or N-mesylhydrazones: synthesis of 1,3-diene compounds
  作者：Kang Wang、Shufeng Chen、Hang Zhang、Shuai Xu、Fei Ye、Yan Zhang、Jianbo Wang

  DOI：10.1039/c6ob00454g

  日期：——

  With palladium catalysis, allyl bromides or chlorides react with α-diazocarbonyl compounds or N-mesylhydrazones to afford 1,3-diene derivatives. The reaction represents a novel and efficient method for the synthesis of 1,3-butadiene derivatives. Mechanistically, the reaction is proposed to follow a pathway involving the formation of a π-allylic palladium carbene complex and subsequent migratory insertion

  在钯催化下，烯丙基溴或氯化物与α-重氮羰基化合物或N-甲磺酰基hydr反应生成1，3-二烯衍生物。该反应代表了一种新颖且有效的合成1,3-丁二烯衍生物的方法。从机理上讲，建议该反应遵循包括形成π-烯丙基钯卡宾配合物和随后的迁移插入的途径。
• Cyclopropylmethyl Palladium Species from Carbene Migratory Insertion: New Routes to 1,3-Butadienes
  作者：Lei Zhou、Fei Ye、Yan Zhang、Jianbo Wang

  DOI：10.1021/ol2034405

  日期：2012.2.3

  Cyclopropylmethyl palladium species can be accessed by Pd-catalyzed reaction of either cyclopropyl N-tosylhydrazone with halide or N-tosylhydrazone with cyclopropyl halide. In both approaches migratory insertion of Pd carbene is the key process. These transformations constitute new approaches toward 1,3-butadiene derivatives.

  环丙基甲基钯物质可通过环丙基N-甲苯磺酰to与卤化物或N-甲苯磺酰with与环丙基卤化物的Pd催化反应获得。在这两种方法中，Pd卡宾的迁移插入都是关键过程。这些转变构成了针对1,3-丁二烯衍生物的新方法。
• Cooperative N-Heterocyclic Carbene/Nickel-Catalyzed Hydroacylation of 1,3-Dienes with Aldehydes in Water
  作者：Hao Liu、You-Feng Han、Zhong-Hua Gao、Chun-Lin Zhang、Congyang Wang、Song Ye

  DOI：10.1021/acscatal.1c05517

  日期：2022.2.4

  carbene/nickel-catalyzed redox-neutral hydroacylation of 1,3-dienes with aldehydes in water was reported. A wide range of aliphatic and aromatic aldehydes were directly coupled with 1,3-dienes, providing synthetically useful β,γ-unsaturated ketones or the corresponding ketones after hydrogenation in moderate to high yields and high atom economy. This protocol first demonstrated the compatibility of NHC catalysis

  报道了1,3-二烯与醛在水中的协同N-杂环卡宾/镍催化的氧化还原中性氢化酰化。多种脂肪族和芳香族醛与 1,3-二烯直接偶联，以中等至高产率和高原子经济性提供合成有用的β,γ-不饱和酮或氢化后的相应酮。该协议首先证明了 NHC 催化与镍催化的相容性。水被用作唯一的溶剂，这在协同金属/有机催化体系中很少被报道。
• Cu(I)-Catalyzed Asymmetric Diamination of Conjugated Dienes
  作者：Haifeng Du、Baoguo Zhao、Weicheng Yuan、Yian Shi

  DOI：10.1021/ol801605w

  日期：2008.10.2

  A Cu(I)-catalyzed asymmetric diamination for a variety of conjugated dienes and a triene with encouraging ee's has been effectively achieved using (R)-DTBM-SEGPHOS as a chiral ligand and di- tert-butyldiaziridinone as the nitrogen source.

  使用 (R)-DTBM-SEGPHOS 作为手性配体和二叔丁基二氮丙啶酮作为氮源，已经有效地实现了 Cu(I) 催化的各种共轭二烯和三烯的不对称二胺化，并具有令人鼓舞的 ee's。
• Intramolecular Cycloisomerization of Aryl-Substituted Alkylidenecyclo­propanes via NHC Palladium-Catalyzed Cascade C-C Bond Cleavage/C-H Activation/C-C Bond Formation
  作者：Xian Huang、Yewei Yang

  DOI：10.1055/s-2008-1078404

  日期：2008.5

  A well-defined N-heterocyclic carbene (NHC) palladium-catalyzed intramolecular cyclization reaction of aryl-substituted alkylidenecyclopropanes (ACP) to 1-aryl dihydronaphthalenes is described. The NHC salts were found to suppress β-hydride elimination from the homoallylpalladium intermediate, which may lead to unwanted alkene formation. A plausible mechanism for the cycloisomerization was proposed.

  本研究描述了一种定义明确的 N-杂环碳烯（NHC）钯催化的芳基取代亚烷基环丙烷（ACP）到 1-芳基二氢萘的分子内环化反应。研究发现，NHC 盐会抑制同质烯丙基钯中间体中的δ-酸酐消除，这可能会导致不必要的烯烃形成。提出了环异构化的合理机制。