2,3-Dihydro-5-phenyl-4H-thiopyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫吡喃类
• 英文名称: 2,3-Dihydro-5-phenyl-4H-thiopyran
• 英文别名: 5-phenyl-3,4-dihydro-2H-thiopyran
• 化学式: C₁₁H₁₂S
• 分子量: 176.282
• InChiKey: ODQJIZQHOKJFDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二氢-2H-硫代吡喃-3(4h)-酮 在 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 5-phenyl-3,6-dihydro-2H-thiopyran 、 2,3-Dihydro-5-phenyl-4H-thiopyran
  参考文献：
  名称：

  通过 Ir 催化不对称加氢对映选择性合成手性砜：制备手性烯丙基和均烯丙基化合物的简便方法

  摘要：

  开发了一种高效且对映选择性 Ir 催化的不饱和砜加氢反应。以优异的对映选择性（高达 98% ee）生产手性环状和无环砜。与 Ramberg-Bäcklund 重排相结合，该反应提供了一种获得具有优异对映选择性（高达 97% ee）和高产率（高达 94%）的手性烯丙基和同型烯丙基化合物的新途径。

  DOI：

  10.1021/ja306731u

文献信息

• Free-Radical Addition of Alkanethiols to Alkynes. Rearrangements of the Intermediate .beta.-(Vinylthio) Radicals
  作者：Luisa Benati、Laura Capella、Pier Carlo Montevecchi、Piero Spagnolo

  DOI：10.1021/jo00089a030

  日期：1994.5

  A variety of 2-mercapto-substituted vinyl radicals have been produced through the free-radical reaction of alkanethiols (including phenethyl, allyl, and benzyl mercaptans) with monosubstituted acetylenes in benzene at 90 degrees C. The 8-(benzylthio)vinyl radicals 6 readily rearranged to (vinylthio)methyl radicals 7 via a novel 1,4-migration of the phenyl group from thiomethyl to vinyl carbon; 2- (phenethylthio)vinyl radicals 12 underwent internal 1,5-hydrogen transfer to form beta-thio-substituted benzyl radicals 13 which in turn suffered fast beta-elimination of vinylthio radicals 18; and 2-(allylthio)vinyl radical 20 underwent kinetically preferred 5-exo cyclization to give the primary radical 26 which could easily rearrange to the more stable ring-expanded radical 25.
• Benati Luisa, Capella Laura, Montevecchi Pier Carlo, Spagnolo Piero, J. Org. Chem, 59 (1994) N 10, S 2818-2823
  作者：Benati Luisa, Capella Laura, Montevecchi Pier Carlo, Spagnolo Piero

  DOI：——

  日期：——
• Enantioselective Synthesis of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation: A Facile Approach to the Preparation of Chiral Allylic and Homoallylic Compounds
  作者：Taigang Zhou、Byron Peters、Matías F. Maldonado、Thavendran Govender、Pher G. Andersson

  DOI：10.1021/ja306731u

  日期：2012.8.22

  A highly efficient and enantioselective Ir-catalyzed hydrogenation of unsaturated sulfones was developed. Chiral cyclic and acyclic sulfones were produced in excellent enantioselectivities (up to 98% ee). Coupled with the Ramberg-Bäcklund rearrangement, this reaction offers a novel route to chiral allylic and homoallylic compounds in excellent enantioselectivities (up to 97% ee) and high yields (up

  开发了一种高效且对映选择性 Ir 催化的不饱和砜加氢反应。以优异的对映选择性（高达 98% ee）生产手性环状和无环砜。与 Ramberg-Bäcklund 重排相结合，该反应提供了一种获得具有优异对映选择性（高达 97% ee）和高产率（高达 94%）的手性烯丙基和同型烯丙基化合物的新途径。