3-methylene-2,2,6-trimethyl-2,3-dihydro-4H-1-benzothiopyran-4-one | 163230-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: 3-methylene-2,2,6-trimethyl-2,3-dihydro-4H-1-benzothiopyran-4-one
• 英文别名: 3-methylidene-2,2,6-trimethylthiochroman-4-one；2,2,6-Trimethyl-3-methylidenethiochromen-4-one
• CAS: 163230-08-8
• 化学式: C₁₃H₁₄OS
• 分子量: 218.32
• InChiKey: MAMRSFJJYRJKEN-UHFFFAOYSA-N

物化性质

• 沸点：
  342.7±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methylene-2,2,6-trimethyl-2,3-dihydro-4H-1-benzothiopyran-4-one 、 亚甲基三苯基膦烷 在 水 作用下， 生成 3-(2-diphenylphosphinoylethyl)-2,2,6-trimethylthiochroman-4-one
  参考文献：
  名称：

  Gabbutt, Christopher D.; Hepworth, John D.; Heron, B. Mark, Journal of Chemical Research, Miniprint, 1995, # 4, p. 805 - 819

  摘要：

  DOI：
• 作为产物：
  描述：

  O-ethyl (2-iodo-4-methylphenyl)sulfanylmethanethioate 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 氢氧化钾 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 苯 为溶剂， 100.0 ℃ 、2.76 MPa 条件下， 反应 10.0h， 生成 3-methylene-2,2,6-trimethyl-2,3-dihydro-4H-1-benzothiopyran-4-one
  参考文献：
  名称：

  Regioselective Carbonylative Heteroannulation of o-Iodothiophenols with Allenes and Carbon Monoxide Catalyzed by a Palladium Complex:  A Novel and Efficient Access to Thiochroman-4-one Derivatives

  摘要：

  The palladium-catalyzed carbonylative ring-forming reactions of 2-iodothiophenol, and the corresponding substituted derivatives, with allenes and carbon monoxide are described. The reactions afford thiochroman-4-ones in good to excellent isolated yields with quite high regioselectivity. The catalytic heteroannulation may involve regioselective addition of the sulfur moiety of the reactants on the more positive end of the allene, arylpalladium formation, CO insertion, subsequent intramolecular cyclization, and then reductive elimination. The regioselectivity is probably governed by electronic effects.

  DOI：

  10.1021/jo9913098

文献信息

• STRUCTURAL STUDIES OF A NOVEL HETEROCYCLIC PHOSPHORANE
  作者：Christopher D. Gabbutt、John D. Hepworth、B. Mark Heron、Alan M. Jones、Eric S. Raper、William Clegg

  DOI：10.1080/10426509808045499

  日期：1998.12.1

  Reaction of 2,2,6-trimethylthiochroman-3,4-dione with an excess of methylenetriphenyl-phosphorane yields the stabilised ylide (4) by way of an alpha -ketol rearrangement. X-Ray crystallography indicates that (4) exists as the (Z)-isomer and provides supporting evidence for an enolate structure.