1-甲基巯基甲基芴 | 101094-37-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 1-甲基巯基甲基芴
• 英文名称: 1-Methylmercaptomethylfluorene
• 英文别名: 1-(methylthiomethyl)fluorene；fluoren-1-ylmethyl-methyl sulfide；Fluoren-1-ylmethyl-methyl-sulfid；1-Methylmercaptomethyl-fluoren；1-Methylthiomethyl-fluoren；1-(methylsulfanylmethyl)-9H-fluorene
• CAS: 101094-37-5
• 化学式: C₁₅H₁₄S
• 分子量: 226.342
• InChiKey: TYMIGGDFZVFZBH-UHFFFAOYSA-N

物化性质

• 熔点：
  77.5 °C
• 沸点：
  367.4±11.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-甲基巯基甲基芴 在 氢溴酸 、 溶剂黄146 、 锌 作用下， 生成 1-甲基芴
  参考文献：
  名称：

  Molecular Rearrangement of Fluorylidene Dimethyl Sulfide to Fluorene-1-dimethyl Sulfide¹

  摘要：

  DOI：

  10.1021/ja01209a011
• 作为产物：
  描述：

  9H-芴-9-硫醇 在 sodium hydroxide 、 乙酸乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 10.5h， 生成 1-甲基巯基甲基芴
  参考文献：
  名称：

  Synthesis and conformational study of 1,1′-ethano-9-9′-bifluorenyl. Anti and gauche conformers of a 9,9′-bifluorenyl derivative and chair and twist conformers of a dibenzo-1,5-cyclooctadiene derivative

  摘要：

  A Hofmann-type elimination of the sulphonium salt (18) under basic conditions led to the formation of a novel o-xylylene derivative (11) which dimerized regioselectively to give the bifluorenyl/dibenzo-1,5-cyclooctadiene derivative (3). The reaction is shown to be kinetically controlled and non-concerted. The two rigid conformers (3a) and (3b) were characterised by their H-1 NMR spectra and they represent respectively the first observed examples of an anti bifluorenyl derivative and a twist dibenzo-1,5-cyclooctadiene derivative. A semiempirical molecular orbital PM3 calculation supported the observed results. Dynamic H-1 NMR studies indicated an interconversion process (3a) reversible (3b) at higher temperatures involving a conformational barrier estimated at 65.2 kJ mol-1.

  DOI：

  10.1016/s0040-4020(01)86322-5

文献信息

• Effects of Solvent Molecular Size on Rates of Topomerization in Organolithium Compounds
  作者：Michinori Oki、Hiroshi Ikeda、Kazuya Kodama、Shinji Toyota

  DOI：10.1246/bcsj.70.2791

  日期：1997.11

  attributable to two species at the lowest temperature of study. From these results, it is concluded that the observed process is the tumbling of the anion in solvent-separated ion pairs with a rapid pre-equilibrium between contact ion pairs and solvent-separated ion pairs, further intervention of solvent molecule(s) into the observed solvent-separated ion pairs being the rate-limiting step. A term, dimensiosolvatic

  取代的 9-芴基锂和 α-（苄硫基）苄基锂的拓扑异构化速率通过动态核磁共振技术在各种醚类溶剂中测定。与体积较小的分子相比，大分子溶剂中的速率较小。这些化合物在溶剂中的紫外-可见光谱表明，这些化合物在小分子溶剂中往往以溶剂分离离子对的形式存在，而在大分子溶剂中则以接触离子对的形式存在。1H NMR 光谱未显示可归因于研究的最低温度下的两种物质的信号。从这些结果可以得出结论，观察到的过程是溶剂分离离子对中阴离子的翻滚，在接触离子对和溶剂分离离子对之间快速预平衡，溶剂分子进一步干预观察到的溶剂分离离子对是限速步骤。提出了一个术语，dimensiosolvatic 效应，其中溶剂分子...
• The Chemistry of Ylids. VI. Dimethylsulfonium Fluorenylide—A Synthesis of Epoxides¹
  作者：A. William Johnson、Robert B. LaCount

  DOI：10.1021/ja01463a040

  日期：1961.1
• Molecular Rearrangement of Fluorylidene Dimethyl Sulfide to Fluorene-1-dimethyl Sulfide¹
  作者：Louis A. Pinck、Guido E. Hilbert

  DOI：10.1021/ja01209a011

  日期：1946.5
• Synthesis and conformational study of 1,1′-ethano-9-9′-bifluorenyl. Anti and gauche conformers of a 9,9′-bifluorenyl derivative and chair and twist conformers of a dibenzo-1,5-cyclooctadiene derivative
  作者：Yee-Hing Lai、Siok-Mun Lee、Soo-Ying Lee、Manyin Yi

  DOI：10.1016/s0040-4020(01)86322-5

  日期：1993.3

  A Hofmann-type elimination of the sulphonium salt (18) under basic conditions led to the formation of a novel o-xylylene derivative (11) which dimerized regioselectively to give the bifluorenyl/dibenzo-1,5-cyclooctadiene derivative (3). The reaction is shown to be kinetically controlled and non-concerted. The two rigid conformers (3a) and (3b) were characterised by their H-1 NMR spectra and they represent respectively the first observed examples of an anti bifluorenyl derivative and a twist dibenzo-1,5-cyclooctadiene derivative. A semiempirical molecular orbital PM3 calculation supported the observed results. Dynamic H-1 NMR studies indicated an interconversion process (3a) reversible (3b) at higher temperatures involving a conformational barrier estimated at 65.2 kJ mol-1.
• NISHIDA, AKIKO;YOSHIMOTO, YOSHIO;FUKUDA, HARUKI;FUJISAKI, SHIZUO;KAJIGAES+, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM., 1984, N 9, 1409-1413
  作者：NISHIDA, AKIKO、YOSHIMOTO, YOSHIO、FUKUDA, HARUKI、FUJISAKI, SHIZUO、KAJIGAES+

  DOI：——

  日期：——