3-methyl-5-phenyl-3H-oxazole-2-thione | 25444-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-5-phenyl-3H-oxazole-2-thione
• 英文别名: 3-Methyl-5-phenyl-2-thioxo-Δ4-oxazolin；3-Methyl-5-phenyl-1,3-oxazolin-2-thion；3-Methyl-5-phenyl-oxazolin-2(3)-thion；3-Methyl-5-phenyl-1,3-oxazole-2-thione
• CAS: 25444-98-8
• 化学式: C₁₀H₉NOS
• 分子量: 191.254
• InChiKey: QTEXWXJUXZUQRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  44.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-5-phenyl-3H-oxazole-2-thione 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 生成 2-Phenacyliden-3-methyl-5-phenyl-1,3-oxazolin
  参考文献：
  名称：

  亚氨基硫代碳酸盐。V. 含硫杂环化合物制备新型偶氮甲碱叶立德和硫代羰基叶立德的制备及性能

  摘要：

  研究了一些新的含有 1,3-dithiolanium 部分的偶氮甲碱叶立德和硫代羰基叶立德的制备和性质。通过 2-(N-甲基-N-苯甲酰基)氨基-(2a)、2-(Np-硝基苄基-N-甲基)氨基-(2b)和分别为 2-(N-carbethoxymethyl-N-methyl)amino-1,3-dithiolanium 盐 (2c)。Azomethine ylides 3a,b 与苯甲醛反应得到1,3-偶极环加合物，这是一类新的螺环原碳酸酯，否则很难获得。从螺环原碳酸酯中消除亚乙基硫很容易得到硫代羰基化合物。在不存在偶极体的情况下，3a 分子内环化得到 1,3-恶唑啉-2-硫酮衍生物。通过去质子化 2-phenacylthio-1 形成硫代羰基叶立德，还研究了 3-恶唑鎓和 2-p-bromophenacylthio-1,3-dithiolanium 盐，以及它们对螺环化合物的不同环化。硫代羰基叶立德16与对硝基苯甲醛反应得到

  DOI：

  10.1246/bcsj.45.1797
• 作为产物：
  描述：

  N-methyl-3-hydroxy-3-phenylazetidine-2-thione 在 盐酸 作用下， 以 氘代二甲亚砜 为溶剂， 反应 42.0h， 以62%的产率得到3-methyl-5-phenyl-3H-oxazole-2-thione
  参考文献：
  名称：

  将羟基β-硫代内酰胺生成恶唑-2-硫酮。一种新型的DMSO促进的氧化。

  摘要：

  3-芳基-3-羟基-1-甲基氮杂环丁烷-2-硫酮与HCl在DMSO中反应，生成3-甲基-5-芳基恶唑-2-硫酮。取代基作用与速率对苯甲醛缩醛水解的作用有关。（17）O标记实验表明产物的氧原子衍生自羟基。CH2Cl2中的三氟乙酸酐/ DMSO也可以促进反应。涉及激活基质的Grob型断裂，然后进行环化或环丙基羰基型重排的机制可以解释这种氧化性重排。

  DOI：

  10.1021/ol802050a

文献信息

• 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
  作者：M. Arbelot、A. Allouche、K. F. Purcell、M. Chanon

  DOI：10.1021/jo00113a010

  日期：1995.4

  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.
• Kjellin,G.; Sandstroem,J., Acta Chemica Scandinavica (1947), 1969, vol. 23, # 8, p. 2879 - 2887
  作者：Kjellin,G.、Sandstroem,J.

  DOI：——

  日期：——
• Synthesis of N-substituted oxazoline-2-thione derivatives: reaction of tetraazapentalene derivatives with α-haloketones
  作者：Noboru Matsumura、Masaaki Tomura、Osamu Mori、Yoshikazu Takamura、Shigeo Yoneda

  DOI：10.1016/s0040-4039(00)99664-3

  日期：1989.1
• MATSUMURA, NOBORU;TOMURA, MASAAKI;MORI, OSAMU;TAKAMURA, YOSHIKAZU;YONEDA,+, TETRAHEDRON LETT., 30,(1989) N7, C. 2259-2262
  作者：MATSUMURA, NOBORU、TOMURA, MASAAKI、MORI, OSAMU、TAKAMURA, YOSHIKAZU、YONEDA,+

  DOI：——

  日期：——