(E)-2-(bis(methylthio)methylene)-1,4-diphenylbut-3-en-1-one | 34631-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-(bis(methylthio)methylene)-1,4-diphenylbut-3-en-1-one
• 英文别名: (E)-2-[bis(methylsulfanyl)methylidene]-1,4-diphenylbut-3-en-1-one
• CAS: 34631-59-9
• 化学式: C₁₉H₁₈OS₂
• 分子量: 326.483
• InChiKey: PWFLZAFTSIIQMG-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(bis(methylthio)methylene)-1,4-diphenylbut-3-en-1-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以63%的产率得到(2-(methylthio)-5-phenylfuran-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Synthesis of 2,3,5-trisubstituted furans from α-formylaroylketene dithioacetals

  摘要：

  A new strategy for the synthesis of 2,3,5-trisbustituted furans from alpha-formylketene dithioacetals is described. The protocol involves a facile conversion of alpha-formylketene dithioacetals to vinylketene dithioacetals via Wittig reaction and subsequent N-bromosuccinimide-mediated cyclization to 2,3,5-trisbustituted furans. Further conversion of the 2-thioalkylfurans thus obtained to 2-aminofurans shows the potential synthetic utility of this new approach. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.128
• 作为产物：
  描述：

  苄基三苯基氯化膦 、 2-benzoyl-3,3-(bismethylsulfanyl)acrylaldehyde 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.08h， 以83%的产率得到(E)-2-(bis(methylthio)methylene)-1,4-diphenylbut-3-en-1-one
  参考文献：
  名称：

  Synthesis of 2,3,5-trisubstituted furans from α-formylaroylketene dithioacetals

  摘要：

  A new strategy for the synthesis of 2,3,5-trisbustituted furans from alpha-formylketene dithioacetals is described. The protocol involves a facile conversion of alpha-formylketene dithioacetals to vinylketene dithioacetals via Wittig reaction and subsequent N-bromosuccinimide-mediated cyclization to 2,3,5-trisbustituted furans. Further conversion of the 2-thioalkylfurans thus obtained to 2-aminofurans shows the potential synthetic utility of this new approach. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.128

文献信息

• Synthesis of Densely Substituted 1,3-Butadienes through Acid-Catalyzed Alkenylations of α-Oxoketene Dithioacetals with Aldehydes
  作者：Changhui Liu、Yanlong Gu

  DOI：10.1021/jo5017234

  日期：2014.10.17

  Aldehydes were proved to be viable reagents for implementing alkenylation of α-oxoketene dithioacetals. AlCl3 was found to be the best catalyst. The established reaction opened an avenue to access densely substituted 1,3-butadiene derivatives. The obtained product bears multiple reactive sites that can be converted into various valuable molecules.

  醛被证明是实现α-氧杂环丁烯二硫缩醛烯基化的可行试剂。发现AlCl 3是最好的催化剂。既定的反应为获取密集取代的1,3-丁二烯衍生物开辟了一条途径。所获得的产物带有多个反应位点，可以将其转化成各种有价值的分子。
• Visible-Light-Driven, Palladium-Catalyzed Heck Reaction of Internal Vinyl Bromides with Styrenes
  作者：Yunlong Li、Haibo Liu、Zilong Huang、Yuan He、Bao-Hua Xu、Hongmei Wang、Zhengkun Yu

  DOI：10.1021/acs.joc.1c00838

  日期：2021.6.18

  Functionalized 1,3-dienes were efficiently accessed from visible-light-driven, palladium-catalyzed Heck reaction of S,S-functionalized internal vinyl bromides with styrenes under mild conditions. This Heck reaction showcased tolerance of a wide array of functional groups, afforded the target products in moderate to excellent yields through a radical reaction pathway. The resultant diene products could

  功能化的 1,3-二烯可通过可见光驱动、钯催化的S , S-官能化内乙烯基溴化物与苯乙烯在温和条件下的Heck 反应有效地获得。这种 Heck 反应展示了对多种官能团的耐受性，通过自由基反应途径以中等至极好的收率提供目标产物。所得二烯产物可以进一步转化为高度官能化的三取代呋喃衍生物。
• Synthesis of 2,3,5-trisubstituted furans from α-formylaroylketene dithioacetals
  作者：K.A. Sasikala、K.A. Kalesh、E.R. Anabha、P. Madhavan Pillai、C.V. Asokan、K.S. Devaky

  DOI：10.1016/j.tetlet.2011.01.128

  日期：2011.4

  A new strategy for the synthesis of 2,3,5-trisbustituted furans from alpha-formylketene dithioacetals is described. The protocol involves a facile conversion of alpha-formylketene dithioacetals to vinylketene dithioacetals via Wittig reaction and subsequent N-bromosuccinimide-mediated cyclization to 2,3,5-trisbustituted furans. Further conversion of the 2-thioalkylfurans thus obtained to 2-aminofurans shows the potential synthetic utility of this new approach. (c) 2011 Elsevier Ltd. All rights reserved.