4-Methyl-2-thia-spiro[4.5]deca-6,8-dien-1-one | 214002-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: 4-Methyl-2-thia-spiro[4.5]deca-6,8-dien-1-one
• 英文别名: 4-Methyl-2-thiaspiro[4.5]deca-6,8-dien-1-one
• CAS: 214002-09-2
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: ODZGSKJVMCNQLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  4-Methyl-2-thia-spiro[4.5]deca-6,8-dien-1-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以23%的产率得到1-(1-methyl-2-sulfanylethyl)-2,4-cyclohexadienylmethanol
  参考文献：
  名称：

  Intramolecular Coupling Reactions of Allylic Thioesters with Diene Iron Tricarbonyl Systems

  摘要：

  Cyclization reactions are reported for a series of allylic thioester derivatives of cyclohexadiene iron tricarbonyl systems, leading to the formation of spiro thialactone derivatives. The overall reaction process is equivalent to a [6 pi + 2 pi] ene reaction in which the pendant alkene, derived from the allyl thioester, is coupled with the diene of the diene-Fe(CO)(3) moiety. While simple substrates were found to undergo this cyclization readily, increased substitution on the pendant double bond led to lower, or zero, yields. Methodology for ring opening of the product thialactones, with or without reductive extrusion of sulfur, is described. The X-ray structure of one of the products (21b) is reported: C15H14FeO4, M-r = 346.17. Crystal dimensions: 0.20 x 0.20 x 0.10 mm: Yelow, clear prism. Mo K alpha radiation (lambda = 0.71073 Angstrom). Monoclinic space group P2(1)/n; alpha = 11.355(2) Angstrom, b = 6.4943(13) Angstrom, c = 20.060(4) Angstrom, beta = 103.30(3)degrees, V = 1439.6 (5) Angstrom(3). Z = 4. Theta = 2.35-27.06 degrees. T = 150 (2) K.

  DOI：

  10.1021/jo980773u
• 作为产物：
  描述：

  tricarbonyl(6-9-η⁴-1-oxo-4-methyl-2-thiaspiro[4,5]deca-6,8-diene)iron 以 正己烷 为溶剂， 反应 1.17h， 以92%的产率得到4-Methyl-2-thia-spiro[4.5]deca-6,8-dien-1-one
  参考文献：
  名称：

  Intramolecular Coupling Reactions of Allylic Thioesters with Diene Iron Tricarbonyl Systems

  摘要：

  Cyclization reactions are reported for a series of allylic thioester derivatives of cyclohexadiene iron tricarbonyl systems, leading to the formation of spiro thialactone derivatives. The overall reaction process is equivalent to a [6 pi + 2 pi] ene reaction in which the pendant alkene, derived from the allyl thioester, is coupled with the diene of the diene-Fe(CO)(3) moiety. While simple substrates were found to undergo this cyclization readily, increased substitution on the pendant double bond led to lower, or zero, yields. Methodology for ring opening of the product thialactones, with or without reductive extrusion of sulfur, is described. The X-ray structure of one of the products (21b) is reported: C15H14FeO4, M-r = 346.17. Crystal dimensions: 0.20 x 0.20 x 0.10 mm: Yelow, clear prism. Mo K alpha radiation (lambda = 0.71073 Angstrom). Monoclinic space group P2(1)/n; alpha = 11.355(2) Angstrom, b = 6.4943(13) Angstrom, c = 20.060(4) Angstrom, beta = 103.30(3)degrees, V = 1439.6 (5) Angstrom(3). Z = 4. Theta = 2.35-27.06 degrees. T = 150 (2) K.

  DOI：

  10.1021/jo980773u