(2-(methylthio)-5-phenylfuran-3-yl)(p-tolyl)methanone | 1293365-27-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-(methylthio)-5-phenylfuran-3-yl)(p-tolyl)methanone
• 英文别名: (4-Methylphenyl)-(2-methylsulfanyl-5-phenylfuran-3-yl)methanone；(4-methylphenyl)-(2-methylsulfanyl-5-phenylfuran-3-yl)methanone
• CAS: 1293365-27-1
• 化学式: C₁₉H₁₆O₂S
• 分子量: 308.401
• InChiKey: NJVDEKUPQFDLAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-(methylthio)-5-phenylfuran-3-yl)(p-tolyl)methanone 、 乙胺 以 乙醇 为溶剂， 以94%的产率得到(2-(ethylamino)-5-phenylfuran-3-yl)(p-tolyl)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 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 25.08h， 生成 (2-(methylthio)-5-phenylfuran-3-yl)(p-tolyl)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

文献信息

• 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.