1,1-双-(4-氯苯基)-1,3-丁二烯 | 92854-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,1-双-(4-氯苯基)-1,3-丁二烯
• 英文名称: 1,1-bis(4-chlorophenyl)buta-1,3-diene
• 英文别名: 4,4'-(buta-1,3-diene-1,1-diyl)bis(chlorobenzene)；1,1-Bis(4-chlorophenyl)-buta-1,3-diene；1-chloro-4-[1-(4-chlorophenyl)buta-1,3-dienyl]benzene
• CAS: 92854-06-3
• 化学式: C₁₆H₁₂Cl₂
• 分子量: 275.177
• InChiKey: XUIAMQRQENDZKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2903999090

反应信息

• 作为反应物：
  描述：

  4-羟基-N-甲基-2-喹啉 、 1,1-双-(4-氯苯基)-1,3-丁二烯 在 manganese(III) triacetate dihydrate 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以69%的产率得到2-[2,2-Bis(4-chlorophenyl)ethenyl]-3,5-dihydro-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'-二氯二苯甲酮 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三(2,6-二甲氧基苯基)磷 、 一水合肼 、 sodium hydroxide 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 5.0h， 生成 1,1-双-(4-氯苯基)-1,3-丁二烯
  参考文献：
  名称：

  Pd（0）催化的烯丙基卤与α-重氮羰基化合物或N-甲磺酰cross的交叉偶联：1,3-二烯化合物的合成†

  摘要：

  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。

  DOI：

  10.1039/c6ob00454g

文献信息

• A novel and efficient method for the olefination of carbonyl compounds with Grignard reagents in the presence of diethyl phosphite
  作者：Tongqiang Wang、Yuanyuan Hu、Songlin Zhang

  DOI：10.1039/c001931c

  日期：——

  The widely available carbonyl compounds react with Grignard reagents in the presence of diethyl phosphite to give the corresponding olefins in good to excellent yields: A range of conjugated dienes, terminal olefins, multisubstituted-alkenes and conjugated enynes could be readily obtained by the method in mild conditions.

  广泛存在的羰基化合物可在以下条件下与Grignard试剂反应： 亚磷酸二乙酯 从而以良好或优异的收率得到相应的烯烃：通过该方法在温和的条件下可以轻松获得一系列共轭二烯，末端烯烃，多取代烯烃和共轭烯类。
• A novel ketone olefination via organozinc reagents in the presence of diphenyl phosphite
  作者：Hua Cui、Ying Li、Songlin Zhang

  DOI：10.1039/c2ob06821d

  日期：——

  Carbonyl compounds react with organozinc reagents in the presence of diphenyl phosphite to give the corresponding olefins. A variety of 1,3-dienes and unsaturated esters were obtained in moderate to excellent yields under mild conditions.

  在二苯基亚磷酸酯存在的条件下，羰基化合物与有机锌试剂反应生成相应的烯烃。在温和条件下，多种1,3-二烯和非饱和酯以中等至优异的产率得到。
• An Example of Ketone Olefination via Praseodymium-Mediated Barbier Reaction in the Presence of Diethyl Phosphite
  作者：Xu yan Cao、Fei Huang、Songlin Zhang

  DOI：10.1055/s-0039-1690096

  日期：2019.7

  The first example of carbon double-bond formation via praseodymium-mediated Barbier type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported. The reaction is highly α-regioselective and conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this

  报道了在亚磷酸二乙酯存在下通过镨介导的酮和烯丙基卤的巴比耶型反应形成碳双键的第一个例子。该反应具有高度的α-区域选择性，可以在温和条件下以一锅法方便地进行。从合成的角度来看，在这种具有实际反应条件的单锅反应中，以中等至良好的收率获得了一系列共轭烯烃。
• 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。
• Neodymium-Promoted Highly Selective Carbon–Carbon Double Bond Formation of Ketones with Allyl Halides in the Presence of Diethyl Phosphite
  作者：Songlin Zhang、Dengbing Xie、Yiqiong Wang、Bo Yang

  DOI：10.1055/s-0040-1707219

  日期：2020.11

  Abstract The carbon–carbon double bond formation via neodymium-mediated Barbier-type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported for the first time. The reaction is highly α-regioselective and was conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to

  摘要 首次报道了在亚磷酸二乙酯存在下，通过钕介导的酮和烯丙基卤化物的Barbier型反应形成碳-碳双键。该反应是高度α-区域选择性的，并且在温和条件下以一锅法方便地进行。从合成的观点来看，在可行的反应条件下，在该一锅法反应中，以中等至良好的产率获得了一系列共轭烯烃。