4-[(methylthio)(2-thienyl)methylene]-2-(2-thienyl)oxazol-5(4H)-one | 1446782-93-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-[(methylthio)(2-thienyl)methylene]-2-(2-thienyl)oxazol-5(4H)-one
• 英文别名: 4-[methylsulfanyl(thiophen-2-yl)methylidene]-2-thiophen-2-yl-1,3-oxazol-5-one
• CAS: 1446782-93-9
• 化学式: C₁₃H₉NO₂S₃
• 分子量: 307.418
• InChiKey: LERSGXAVUHSFLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-[(methylthio)(2-thienyl)methylene]-2-(2-thienyl)oxazol-5(4H)-one 、 sodium butanolate 以80%的产率得到
  参考文献：
  名称：

  Synthesis of 2,4,5-Trisubstituted Thiazoles via Lawesson’s Reagent-Mediated Chemoselective Thionation–Cyclization of Functionalized Enamides

  摘要：

  An efficient route to 2-phenyl/(2-thienyl)-5-(het)aryl/(methylthio)-4-functionalized thiazoles via one-step chemoselective thionation-cyclization of highly functionalized enamides mediated by Lawesson's reagent is reported. These enamide precursors are obtained by nucleophilic ring-opening of 2-phenyl/(2-thienyl)-4-[bis(methylthio)/(methylthio)(het)arylmethylene]-5-oxazolones with alkoxides and a variety of primary aromatic/aliphatic amines or amino acid esters, leading to the introduction of an ester, an N-substituted carboxamide, or a peptide functionality in the 4-position of the product thiazoles.

  DOI：

  10.1021/jo401208u

文献信息

• Synthesis of 2,5-Bis(hetero)aryl 4′-Substituted 4,5′-Bisoxazoles via Copper(I)-Catalyzed Domino Reactions of Activated Methylene Isocyanides with 2-Phenyl- and 2-(2-Thienyl)-4-[(aryl/heteroaryl)(methylthio)methylene]oxazol-5(4<i>H</i>)-ones
  作者：Somaraju Yugandar、Anand Acharya、Hiriyakkanavar Ila

  DOI：10.1021/jo400317g

  日期：2013.4.19

  An efficient straightforward synthesis of 2,5,4′-trisubstituted 4,5′-bisoxazoles via copper(I)-catalyzed domino reactions of 2-phenyl- and 2-(2-thienyl)-4-[(aryl/heteroaryl)methylene]-5-oxazolones with activated methylene isocyanides has been reported. The overall domino process comprised of formation of one C–C and two C–O bonds involves initial nucleophilic ring opening of oxazolones by cupriomethylene

  通过铜（I）催化的2-苯基-和2-（2-噻吩基）-4-[（芳基/杂芳基）多米诺骨牌反应，有效而直接地合成2,5,4'-三取代的4,5'-双恶唑已经报道了具有活化的亚甲基异氰酸酯的亚甲基] -5-恶唑酮。由形成一个C–C和两个C–O键组成的整个多米诺过程涉及通过亚甲基二亚甲基溴化异恶唑酮的初始亲核开环，然后在铜催化剂存在下顺序构建两个恶唑环。通过使用各种杂芳基和芳基取代的恶唑酮和活化的亚甲基异氰酸酯，已经证明了反应的广泛的底物范围和优异的官能团相容性，得到具有三个潜在多样性点的双恶唑。