1,2-bis(4-chlorophenyl)prop-2-en-1-one | 40281-53-6

• 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: 1,2-bis(4-chlorophenyl)prop-2-en-1-one
• 英文别名: 4'-Chlor-2-(p-chlorphenyl)-acrylophenon
• CAS: 40281-53-6
• 化学式: C₁₅H₁₀Cl₂O
• 分子量: 277.15
• InChiKey: QKJKYOQYFDUOKU-UHFFFAOYSA-N

物化性质

• 沸点：
  423.8±45.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  ethyl 5,5-diphenylpenta-2,3,4-trienoate 、 1,2-bis(4-chlorophenyl)prop-2-en-1-one 在 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以88%的产率得到ethyl 5-(4-chlorobenzoyl)-5-(4-chlorophenyl)-3-(diphenylmethylene)cyclopent-1-ene-carboxylate
  参考文献：
  名称：

  5,5-二芳基戊基2,3,4-三烯酸乙酯与芳族醛和α，β-不饱和羰基化合物的膦催化区域选择性[3 + 2]环加成反应

  摘要：

  AbstractTributylphosphine‐catalyzed regioselective [3+2] cycloadditions between ethyl 5,5‐diarylpenta‐2,3,4‐trienoate 1 and various aromatic aldehydes 2 to produce a wide variety of polysubstituted 2,5‐dihydrofurans 3, and between 1 and β‐unsubstituted α,β‐unsaturated carbonyl compounds 5 to give polysubstituted cyclopentenes 6 with a quaternary carbon center, are reported. In both cases the reaction partners approach each other via the sterically less hindered orientation to afford the target products in excellent regioselectivity. The reaction mechanism involved first the generation of a zwitterionic intermediate between the butatriene 1 and PBu3. For the formation of 2,5‐dihydrofurans 3, the preferred cyclization mode encompassed the nucleophilic attack of the α‐position of butatriene to the aldehydic carbon of 2, followed by the ring closure between the aldehydic oxygen of 2 and the γ‐position of butatriene, which is the first report of a normal [3+2] cycloaddition between cumulenes and aldehydes. For the formation of cyclopentenes 6, the reaction involved attack of the γ‐position of the butatriene to the electron‐deficient β‐position of the α,β‐unsaturated carbonyl compounds 5, followed by the ring closure between the α‐position of 5 and the α‐position of butatriene, which shows a different regioselectivity to the previously reported [3+2] cycloadditions between butatriene and olefins.magnified image

  DOI：

  10.1002/adsc.201301000
• 作为产物：
  描述：

  聚合甲醛 、 1,2-双(4-氯苯基)乙酮 在 哌啶 作用下， 以 甲醇 为溶剂， 生成 1,2-bis(4-chlorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  中枢神经系统制剂。4. 3-氨基-2-苯基苯乙酮的类似物。

  摘要：

  DOI：

  10.1021/jm00282a010

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：ASTRAZENECA AB

  公开号：WO2004011410A1

  公开（公告）日：2004-02-05

  Compounds of formula (I):wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  式(I)的化合物：其中变量基团如定义内；用于抑制11βHSD1。
• Ligand-Free Palladium-Catalyzed Carbonylative Suzuki Couplings of Vinyl Iodides with Arylboronic Acids under Substoichiometric Base Conditions
  作者：Zhiyuan Yang、Pei-Xue Gong、Wei Han、Junjie Chen、Jie Zhang、Xu Gong

  DOI：10.1055/a-1511-0435

  日期：2021.7

  A ligand-free palladium-catalyzed carbonylation of vinyl iodides with arylboronic acids, permitting the synthesis of chalcones and α-branched enones, has been established. This reaction proceeds smoothly at ambient pressure and temperature, and works well even with a substoichiometric amount of base. Importantly, this mild, efficient, and operationally simple protocol is suitable for the late-stage

  已经建立了无配体钯催化的乙烯基碘与芳基硼酸的羰基化反应，允许合成查耳酮和α-支链烯酮。该反应在环境压力和温度下平稳进行，即使使用亚化学计量的碱也能很好地进行。重要的是，这种温和、高效且操作简单的方案适用于表雄酮衍生的复杂分子的后期功能化。铂催化、乙烯基碘、芳基硼酸、查耳酮、烯酮、铃木-宫浦反应
• Ketones
  申请人：Barton John Peter

  公开号：US20050272036A1

  公开（公告）日：2005-12-08

  Compounds of formula (I): wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  描述了式(I)的化合物：其中变量基团如定义的那样；用于抑制11βHSD1。
• KETONES
  申请人：AstraZeneca AB

  公开号：EP1549600A1

  公开（公告）日：2005-07-06
• JPH0848647A
  申请人：——

  公开号：JPH0848647A

  公开（公告）日：1996-02-20