trans-thiabicyclo<4.3.0>nonane | 7493-02-9

• 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: trans-thiabicyclo<4.3.0>nonane
• 英文别名: trans-2-thiahydrindane；(+/-)-trans-octahydro-benzo[c]thiophene；(+/-)-trans-Octahydro-benzo[c]thiophen；Benzo[c]thiophene, octahydro-, trans-；(3aS,7aS)-1,3,3a,4,5,6,7,7a-octahydro-2-benzothiophene
• CAS: 7493-02-9；17739-77-4；38802-19-6；51153-54-9；54053-76-8
• 化学式: C₈H₁₄S
• 分子量: 142.265
• InChiKey: SJXUGVWKLLOJDR-HTQZYQBOSA-N

物化性质

• 熔点：
  -3.61 °C
• 沸点：
  122.5-123.5 °C(Press: 20 Torr)
• 密度：
  1.0430 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  trans-thiabicyclo<4.3.0>nonane 在 双氧水 作用下， 生成 cis-8-thiabicyclo[4.3.0]nonane 8,8-dioxide
  参考文献：
  名称：

  PREPARATION AND PHYSICAL PROPERTIES OF SULFUR COMPOUNDS RELATED TO PETROLEUM. IV. cis- AND trans-2-THIAHYDRINDAN AND 2-THIADECALIN

  摘要：

  DOI：

  10.1021/jo01374a007
• 作为产物：
  描述：

  trans-1,2-bis(hydroxymethyl)cyclohexane di-p-toluene-sulfonate 在 NaS 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 trans-thiabicyclo<4.3.0>nonane
  参考文献：
  名称：

  Conformational equilibrium in 8-methyl-cis-2-thiahydrindane and 8-methyl-cis-2-oxahydrindane by13C NMR spectroscopy

  摘要：

  AbstractThe preferred conformation of 8‐methyl‐cis‐thiahydrindane has been both estimated by 13C NMR chemical shifts and determined by low temperature 13C NMR spectroscopy to be the conformer with the methyl group equatorial with respect to the cyclohexane ring. This result is in disagreement with the interpretation of the temperature dependence of the CD spectra of (+) and (−) 8‐methyl‐cis‐2‐thiahydrindane, whereby the conformation with the methyl group axial with respect to the cyclohexane ring was claimed to be the preferred conformation. The preferred conformation of the related oxygen heterocycle, 8‐methyl‐cis‐2‐oxahydrindane, has been estimated by 13C NMR chemical shifts to be the conformer with the methyl group axial with respect to the cyclohexane ring. Possible reasons for these observations are discussed.

  DOI：

  10.1002/mrc.1270160403

文献信息

• Metallacycle Transfer from Zirconium to Main Group Elements: A Versatile Synthesis of Heterocycles
  作者：Paul J. Fagan、William A. Nugent、Joseph C. Calabrese

  DOI：10.1021/ja00084a031

  日期：1994.3

  The reaction of zirconium metallacycles is used to produce a variety of main group heterocycles including borole Diels-Alder dimers, galloles, indacyclopentadienes, siloles, germoles, stannoles, phospholes, arsoles, stiboles, bismoles, thiophenes, selenophenes, dihydrothiophenes, dihydroselenophenes, tetrahydrothiophenes, tetrahydroselenophenes, stannacyclopentanes, phospholenes, and isothiazoles.

  锆金属环的反应用于生产各种主族杂环，包括硼醇 Diels-Alder 二聚体、galloles、indacyclopentadienes、siloles、germoles、stannoles、phospholes、arsoles、stiboles、bismoles、噻吩、硒代四氢噻吩、二氢噻吩、二氢噻吩、四氢硒酚、锡环戊烷、磷烯和异噻唑。讨论了 1-苯基-2,3,4,5-四甲基硼的硼醇 Diels-Alder 二聚体的 X 射线晶体学研究，并与 7-降冰片烯基碳鎓离子的结构进行了比较。描述了这种金属环转移反应的范围和潜力
• 13C13C vicinal coupling constants of sulphonium cations
  作者：G. Barbarella、P. Dembech

  DOI：10.1002/mrc.1270160305

  日期：1981.7

  AbstractThe 13C13C vicinal coupling constants of cyclic sulphonium cations, with the labelled carbon bound to the positively charged sulphur atom, cannotbe related to the dihedral angle ϕ by a Karplus type correlation.
• Zirconium-mediated ring construction from dienes: remarkable effect of ligands on stereochemistry
  作者：William A. Nugent、Douglass F. Taber

  DOI：10.1021/ja00198a073

  日期：1989.8
• Synthesis of 1-substituted trans-2-thiahydrindanes and 3-substituted trans-2-thiadecalins
  作者：N. P. Volynskii、O. L. Alikhanova

  DOI：10.1007/bf01172271

  日期：1991.8

  Methods of synthesis of 1-R-trans-2-thiahydrindanes and 3-R-trans-2-thiadecalins from trans-1-methoxymethyl-2-chlorocyclohexane have been developed. The order of the chromatographic elution of the isomeric sulfides formed has been found. The configurations of the compounds have been established by H-1 and C-13 NMR spectroscopy. The characteristics of the intermediate and final compounds are given. The splitting of 1-R-trans-2-oxahydrindanes and 3-R-trans-2-oxadecalins by the PBr3/conc. HBr system has been effected.