5Z-5-[(5-methyl-2-thiophenyl)methylene]-2(5H)-furanone | 5705-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5Z-5-[(5-methyl-2-thiophenyl)methylene]-2(5H)-furanone
• 英文别名: (5Z)-5-[(5-Methyl-2-thienyl)methylene]-2(5H)-furanone；(5Z)-5-[(5-methylthiophen-2-yl)methylidene]furan-2-one
• CAS: 5705-62-4
• 化学式: C₁₀H₈O₂S
• 分子量: 192.238
• InChiKey: YBBZWBTVSIDANF-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-甲基-2-噻吩甲醛 在 三乙烯二胺 、 H-ZSM-5 zeolite 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 28.0h， 生成 5Z-5-[(5-methyl-2-thiophenyl)methylene]-2(5H)-furanone
  参考文献：
  名称：

  ZEOLITE MEDIATED STEREOSELECTIVE SYNTHESIS OF γ-ALKYLIDENEBUTENOLIDES

  摘要：

  Stereoselective synthesis of Z-gamma-alkylidenebutenolides has been achieved through H-ZSM 5 mediated dehydration.

  DOI：

  10.1081/scc-120004083

文献信息

• Stereoselective synthesis of freelingyne and related γ-alkylidenebutenolides via vinylogous Mukaiyama aldol additions
  作者：Frank von der Ohe、Reinhard Brückner

  DOI：10.1039/b002903n

  日期：——

  Following the strategy of Scheme 1, a Mukaiyama aldol addition/anti-elimination route to stereopure γ-alkylidenebutenolides 4 was established. The addition giving 27 was only moderately diastereoselective but the products lk- and ul-27 were chromatographically separable (Scheme 4). They underwent highly selective anti-eliminations in the presence of triflic anhydride–pyridine or Burgess' reagent, furnishing

  遵循的策略 方案1，建立了向立体纯γ-亚烷基丁烯内酯4的Mukaiyama醛加成/抗消除途径 。给出的加成27仅具有中等非对映选择性，但产物lk-和ul - 27在色谱上是可分离的（方案4）。他们在三氟甲磺酸酐-吡啶或伯吉斯试剂的存在下进行了高度选择性的抗消除作用，分别提供了含噻吩的丁烯内酯Z-和E - 28（方案5）。的向山羟醛反应导致化合物29 100％ LK -选择性时由BF介导的3醚合物和87:13微升-选择性在ZnBr存在2（方案6）。所产生的丁烯羟的斯蒂芬-卡斯特罗接头LK -和UL - 29与3-ethynylfuran与立体化学完整性的完整保护（进行方案7）。随后的抗水-eliminations物最好通过与DEAD-PPH治疗实现3。它们提供freelingyne（ž - 9）配有DS = 92：8及其异构体ë - 9与DS = 98：2（方案8）。类似地，不同取代的（三甲
• Direct Synthesis of Heteroarylethynes via Palladium-catalyzed Coupling of Heteroaryl Halides with EthynylzincHalides. Its Application to an Efficient Synthesis of a Thiophenelactone from Chamaemelum nobile L.
  作者：Ei-ichi Negishi、Caiding Xu、Ze Tan、Martin Kotora

  DOI：10.3987/com-97-s79

  日期：——

  A variety of terminal alkynes containing a heteroaryl group can be directly and selectively synthesized by the Pd-catalyzed coupling of heteroaryl iodides or bromides with ethynylzinc halides. Various compounds of this class containing furan, thiophene, and pyridine have been prepared, and the procedure has been applied to an efficient and selective synthesis of a thiophenelactone from Chamaemelum nobile L.
• ANTONIOLETTI, R.;DAURIA, M.;DE, MICO, A.;PIANCATELLI, G.;SCETTRI, A., TETRAHEDRON, 1984, 40, N 19, 3805-3808
  作者：ANTONIOLETTI, R.、DAURIA, M.、DE, MICO, A.、PIANCATELLI, G.、SCETTRI, A.

  DOI：——

  日期：——
• ZEOLITE MEDIATED STEREOSELECTIVE SYNTHESIS OF γ-ALKYLIDENEBUTENOLIDES
  作者：N. Sundar、Mrinal K. Kundu、P. Veera Reddy、G. Mahendra、Sujata V. Bhat

  DOI：10.1081/scc-120004083

  日期：2002.1.1

  Stereoselective synthesis of Z-gamma-alkylidenebutenolides has been achieved through H-ZSM 5 mediated dehydration.