2,3-dihydro-4-phenylthiophene | 99059-46-8

• 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: 2,3-dihydro-4-phenylthiophene
• 英文别名: 4-phenyl-2,3-dihydro-thiophene；4-Phenyl-2,3-dihydro-thiophen；3-Phenyl-2-thiolene；4-phenyl-2,3-dihydrothiophene
• CAS: 99059-46-8
• 化学式: C₁₀H₁₀S
• 分子量: 162.255
• InChiKey: BXSCECHLEACCND-UHFFFAOYSA-N

物化性质

• 沸点：
  280.9±30.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-4-phenylthiophene 在 双氧水 、 溶剂黄146 作用下， 生成 3-phenyl-4,5-dihydrothiophene-1,1-dioxide
  参考文献：
  名称：

  The Synthesis of Di- and Terthienyls^1,2

  摘要：

  DOI：

  10.1021/ja01565a058
• 作为产物：
  描述：

  sodium thiophenolate 在 偶氮二异丁腈 、 氘代甲醇-d 、 乙酸-D1 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 4.5h， 生成 2,3-dihydro-4-phenylthiophene
  参考文献：
  名称：

  Tin Radical Addition to Alkynyl Sulfides: Reactivity of the Intermediate Thioalkyl-Substituted .beta.-(Tributylstannyl)vinyl Radicals

  摘要：

  Phenyl and benzyl alkynyl sulfides 1a-g and 3a, phenylalkynylamines 19a,b, ethers 22a,b, and selenide 31 reacted with tributyltin radicals to give intermediate beta-stannylvinyl radicals, whose fate depended on the nature of the side chain. 4-Phenylthio-substituted but-1-en-2-yl radicals underwent stereospecific 5-exo cyclization on the adjacent phenyl ring. The resulting spirocyclohexadienyl radicals gave thiophenes and thiopyrans by carbon-sulfur bond scission or ring expansion on the exocyclic double bond, respectively. Similar behavior was exhibited by the corresponding selenium-containnig radical, which afforded a selenophene almost exclusively. (Benzylthio) alkyl-substituted radicals gave products deriving from intramolecular S(H)2 substitution at the sulfur atom, whereas propargyl sulfides yielded a stannylallene via a beta-scission reaction. No 6(or more)-membered ring closure was observed with pentynyl and hexynyl phenyl sulfides 1b,c, which gave only the (E)-addition products of tin hydride; oxygen- and nitrogen-containing vinyl radicals also gave the (E)-adducts exclusively. An interaction between the unpaired electron orbital and the empty low-energy orbitals of the heteroatom might explain why sulfur and selenium can undergo 5-exo cyclization.

  DOI：

  10.1021/jo00091a025

文献信息

• Capella Laura, Montevecchi Pier Carlo, Nanni Daniele, J. Org. Chem, 59 (1994) N 12, S 3368- 3374
  作者：Capella Laura, Montevecchi Pier Carlo, Nanni Daniele

  DOI：——

  日期：——
• Tin Radical Addition to Alkynyl Sulfides: Reactivity of the Intermediate Thioalkyl-Substituted .beta.-(Tributylstannyl)vinyl Radicals
  作者：Laura Capella、Pier Carlo Montevecchi、Daniele Nanni

  DOI：10.1021/jo00091a025

  日期：1994.6

  Phenyl and benzyl alkynyl sulfides 1a-g and 3a, phenylalkynylamines 19a,b, ethers 22a,b, and selenide 31 reacted with tributyltin radicals to give intermediate beta-stannylvinyl radicals, whose fate depended on the nature of the side chain. 4-Phenylthio-substituted but-1-en-2-yl radicals underwent stereospecific 5-exo cyclization on the adjacent phenyl ring. The resulting spirocyclohexadienyl radicals gave thiophenes and thiopyrans by carbon-sulfur bond scission or ring expansion on the exocyclic double bond, respectively. Similar behavior was exhibited by the corresponding selenium-containnig radical, which afforded a selenophene almost exclusively. (Benzylthio) alkyl-substituted radicals gave products deriving from intramolecular S(H)2 substitution at the sulfur atom, whereas propargyl sulfides yielded a stannylallene via a beta-scission reaction. No 6(or more)-membered ring closure was observed with pentynyl and hexynyl phenyl sulfides 1b,c, which gave only the (E)-addition products of tin hydride; oxygen- and nitrogen-containing vinyl radicals also gave the (E)-adducts exclusively. An interaction between the unpaired electron orbital and the empty low-energy orbitals of the heteroatom might explain why sulfur and selenium can undergo 5-exo cyclization.
• The Synthesis of Di- and Terthienyls^1,2
  作者：Hans Wynberg、A. Logothetis、D. VerPloeg

  DOI：10.1021/ja01565a058

  日期：1957.4