4-methyl-5-phenyl-2-thioxo-1,3-dithiole | 17784-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methyl-5-phenyl-2-thioxo-1,3-dithiole
• 英文别名: 4-methyl-5-phenyl-1,3-dithiol-2-thione；4-methyl-5-phenyl-[1,3]dithiole-2-thione；5-Phenyl-4-methyl-1,3-dithiol-2-thion；4-Methyl-5-phenyl-1,3-dithiole-2-thione
• CAS: 17784-41-7
• 化学式: C₁₀H₈S₃
• 分子量: 224.372
• InChiKey: UKVFUQRCLMVKNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-5-phenyl-2-thioxo-1,3-dithiole 、 碘甲烷 在 ΔG(excit.) 作用下， 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Specific Molecular Orbital Contributions to Nucleophilicity. The Thiocarbonyl Group as Priviledged Monitor to Pinpoint Active and Less Active Molecular Orbitals in Reactions with Methylating Agents

  摘要：

  The rate constants for 41 compounds bearing a C=S function reacting with MeX (X = I, Tos) span 7 orders of magnitude. The PES spectra of these compounds display two very low energy peaks, which stand clearly apart from the other peaks. These two peaks correspond to the pi orbitals of the C-S group; one is its CS pi bonding orbital oriented out of the molecular plane (pi(CS)) and the other its p-type in-plane lone pair orbital (pi(S)). For some of the compounds, the HOMO is the pi(CS) orbital and for others the HOMO is the ns lone pair orbital. The best correlation (R = 0.96) between rate constants h and PES data is obtained when In(k) is plotted against the inverse of PES energy of the pi(S) lone pair orbital. Whether this lone pair orbital is the HOMO or the next lower HOMO has no importance. A modest correlation (R = 0.78) is obtained when In(k) is plotted against the inverse of PES energy of the pi(CS) bonding orbital, An attempt to correlate the calculated energy of the third highest occupied orbital (from AM1 calculations) with In(h) provides a complete scattering of data (R < 0.1), but the calculated energy of the second lone pair orbital sigma(S) (approximate to 90 kcal mol-l deeper than the HOMO) correlates reasonably with In(h) (R = 0.88). The energies of the S 2s and 2p core orbitals (calculated for 13 cyclic compounds with the HF/3-21G technique to be 4000 to 5500 kcal mol(-1) deeper than HOMO) correlate with In(k) (R = 0.86) as well as does that of the second lone pair orbital os. These results are the first where both frontier orbitals and core orbitals display correlation with overall reactivity. They are discussed in terms of direct (perturbational) versus indirect (nonperturbational) concepts.

  DOI：

  10.1021/jo00113a010
• 作为产物：
  描述：

  4-(1-苯基-丙烯基)-吗啉 以55%的产率得到
  参考文献：
  名称：

  FANGHAENEL E., J. PRAKT. CHEM. , 1975, 317, NO 1, 123-136

  摘要：

  DOI：

文献信息

• Yamada, Shuzo; Mino, Norihisa; Nakayama, Noboru, Journal of the Chemical Society. Perkin transactions I, 1984, # 11, p. 2497 - 2499
  作者：Yamada, Shuzo、Mino, Norihisa、Nakayama, Noboru、Ohashi, Mamoru

  DOI：——

  日期：——
• Free Radical Reaction of Diisopropyl Xanthogen Disulfide with Unsaturated Systems
  作者：Yves Gareau、André Beauchemin

  DOI：10.3987/com-98-8230

  日期：——

  1,3-Dithiol-2-ones are prepared in one pot reaction from commercially available diisopropyl xanthogen disulfide (2) and alkynes under radical conditions. The 5-membered heterocycle is formed via a ring closure of vinyl radical (7) resulting from the thio radical addition of 5 to an alkyne. The reaction worked best for alkynes conjugated with a C=C double bond. The oxygen atoms of reagent (2) could be replaced by sulfur and this new reagent furnished 1,3-dithiol-2-thiones under radical conditions.
• NAKADZAVA, XITOSI;OTSUKA, MASARI;MATSUDA, XIDEHAKI;KATORI, TATSUXIKO;IRIN+
  作者：NAKADZAVA, XITOSI、OTSUKA, MASARI、MATSUDA, XIDEHAKI、KATORI, TATSUXIKO、IRIN+

  DOI：——

  日期：——
• YAMADA, SHUZO;MINO, NORIHISA;NAKAYAMA, NOBORU;OHASHI, MAMORU, J. CHEM. SOC. PERKIN TRANS., 1984, N 11, 2497-2499
  作者：YAMADA, SHUZO、MINO, NORIHISA、NAKAYAMA, NOBORU、OHASHI, MAMORU

  DOI：——

  日期：——
• OHASHI M.; MINO N.; NAKAYAMA N.; JAMADA S., CHEM. LETT., 1978, NO 11, 1189-1190
  作者：OHASHI M.、 MINO N.、 NAKAYAMA N.、 JAMADA S.

  DOI：——

  日期：——

表征谱图