5-(4-Methoxyphenyl)-1,1-ethylendithiopenta-1,4-dien-3-on | 97853-38-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 5-(4-Methoxyphenyl)-1,1-ethylendithiopenta-1,4-dien-3-on
• 英文别名: 1-(1,3-Dithiolan-2-ylidene)-4-(4-methoxyphenyl)but-3-en-2-one
• CAS: 97853-38-8
• 化学式: C₁₄H₁₄O₂S₂
• 分子量: 278.396
• InChiKey: JMFPBMBHZICPEB-UHFFFAOYSA-N

物化性质

• 沸点：
  463.7±45.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-Methoxyphenyl)-1,1-ethylendithiopenta-1,4-dien-3-on 在 三氟化硼乙醚 、 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  宝石-二烷硫基三苯炔的可调控分子内环化形成苯并[ f ] -1-茚满酮骨架

  摘要：

  从容易获得的宝石-二烷硫基三苯炔通过分子内环化反应，已经开发出了苯并[ f ] -1-茚满酮骨架的原子经济路线。分子内环化的化学选择性可以通过反应中所用的碱和气体气氛的类型来调节，因此可以以良好至极好的收率合成相应的官能化苯并[ f ] -1-茚满酮。

  DOI：

  10.1021/ol5034332
• 作为产物：
  描述：

  1-(1,3-dithiolan-2-ylidene)propan-2-one 、 4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以95%的产率得到5-(4-Methoxyphenyl)-1,1-ethylendithiopenta-1,4-dien-3-on
  参考文献：
  名称：

  α-Alkenoyl Ketene S,S-Acetal-Based Multicomponent Reaction: An Efficient Approach for the Selective Construction of Polyfunctionalized Cyclohexanones

  摘要：

  A versatile multicomponent reaction based on the new four-carbon synthons alpha-alkenoyl ketene S,S-acetals 1 has been developed. This three-component reaction of readily available alpha-alkenoyl ketene S,S-acetals 1 with aldehydes 2 and active methylene compounds 3 proceeds smoothly in acidic medium (glacial acetic acid in tetrahydrofuran) to give various polyfunctionalized cyclohexanones 4, 5, and 6 in a highly regio- and diastereoselective manner with good to excellent yields. The reaction can tolerate a broad range of substituents in the three components involved and is proposed to proceed via a tandem Knoevenagel-intermolecular Michael-intramolecular Michael sequence. As an extension of the synthetic application of polyfunctionalized cyclohexanones obtained, unsymmetrical biaryls 7 were synthesized in almost quantitative yields by simple transformations of the corresponding cycloadducts 6.

  DOI：

  10.1021/jo900217g

文献信息

• Palladium-Catalyzed Cross-Coupling of Internal Alkenes with Terminal Alkenes to Functionalized 1,3-Butadienes Using CH Bond Activation: Efficient Synthesis of Bicyclic Pyridones
  作者：Haifeng Yu、Weiwei Jin、Chenglin Sun、Jiping Chen、Wangmin Du、Songbo He、Zhengkun Yu

  DOI：10.1002/anie.201002737

  日期：——

  cross‐coupling of internal alkenes of α‐oxoketene dithioacetals with terminal alkenes has been successfully realized by palladium‐catalyzed CH bond activation, affording functionalized 1,3‐butadienes. Condensation of the resultant 1,3‐butadienes by diamines efficiently produced potentially bioactive bicyclic pyridone derivatives (see scheme).

  甲高度选择性直接交叉偶联与末端烯烃α-oxoketene二硫的内部烯烃的已通过钯催化的C ^成功地实现 H键活化，得到官能化的1,3-丁二烯。二胺将所得的1,3-丁二烯缩合可有效产生具有潜在生物活性的双环吡啶酮衍生物（请参见方案）。
• Matschiner, H.; Ruettinger, H. H.; Austen, S., Journal fur praktische Chemie (Leipzig 1954), 1985, vol. 327, # 1, p. 45 - 50
  作者：Matschiner, H.、Ruettinger, H. H.、Austen, S.

  DOI：——

  日期：——
• α-Alkenoyl Ketene <i>S</i>,<i>S</i>-Acetal-Based Multicomponent Reaction: An Efficient Approach for the Selective Construction of Polyfunctionalized Cyclohexanones
  作者：Yuhui Ma、Mang Wang、Dan Li、Bahargul Bekturhun、Jun Liu、Qun Liu

  DOI：10.1021/jo900217g

  日期：2009.4.17

  A versatile multicomponent reaction based on the new four-carbon synthons alpha-alkenoyl ketene S,S-acetals 1 has been developed. This three-component reaction of readily available alpha-alkenoyl ketene S,S-acetals 1 with aldehydes 2 and active methylene compounds 3 proceeds smoothly in acidic medium (glacial acetic acid in tetrahydrofuran) to give various polyfunctionalized cyclohexanones 4, 5, and 6 in a highly regio- and diastereoselective manner with good to excellent yields. The reaction can tolerate a broad range of substituents in the three components involved and is proposed to proceed via a tandem Knoevenagel-intermolecular Michael-intramolecular Michael sequence. As an extension of the synthetic application of polyfunctionalized cyclohexanones obtained, unsymmetrical biaryls 7 were synthesized in almost quantitative yields by simple transformations of the corresponding cycloadducts 6.
• Formation of Benzo[<i>f</i>]-1-indanone Frameworks by Regulable Intramolecular Annulations of <i>gem</i>-Dialkylthio Trienynes
  作者：Zhongxue Fang、Ying Liu、Badru-Deen Barry、Peiqiu Liao、Xihe Bi

  DOI：10.1021/ol5034332

  日期：2015.2.20

  intramolecular annulations. The chemoselectivity of the intramolecular cyclizations can be regulated by both the base and the type of gas atmosphere used in the reaction, thus allowing the divergent synthesis of the corresponding functionalized benzo[f]-1-indanones in good to excellent yields.

  从容易获得的宝石-二烷硫基三苯炔通过分子内环化反应，已经开发出了苯并[ f ] -1-茚满酮骨架的原子经济路线。分子内环化的化学选择性可以通过反应中所用的碱和气体气氛的类型来调节，因此可以以良好至极好的收率合成相应的官能化苯并[ f ] -1-茚满酮。