1-methylcyclopropyl phenyl sulfide | 36195-51-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-methylcyclopropyl phenyl sulfide
• 英文别名: 1-Methylcyclopropylphenylsulfid；[(1-Methylcyclopropyl)sulfanyl]benzene；(1-methylcyclopropyl)sulfanylbenzene
• CAS: 36195-51-4
• 化学式: C₁₀H₁₂S
• 分子量: 164.271
• InChiKey: JDBDALLFROLQSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,1-bis(phenylthio)cyclopropane 以49%的产率得到
  参考文献：
  名称：

  COHEN T.; DANIEWSKI W. M.; WEIGENFELD R. B., TETRAHEDRON LETT., 1978, NO 47, 4665-4668

  摘要：

  DOI：

文献信息

• A New and Convenient Synthetic Method for Cyclopropyl Phenyl Sulfides
  作者：Kazuhiko Tanaka、Hideki Uneme、Shuichi Matsui、Aritsune Kaji

  DOI：10.1246/bcsj.55.2965

  日期：1982.9

  The reactions of a variety of 1,3-bis(phenylthio)propanes with butyllithium have been shown to produce cyclopropyl phenyl sulfides in good to high yields. A new and convenient in situ preparation of 1-lithiocyclopropyl phenyl sulfide can be readily carried out by treating 1,3-bis(phenylthio)propane with 2 equiv. of butyllithium at 0 °C in THF. The reaction with electrophiles proceeds in good yield

  各种 1,3-双（苯硫基）丙烷与丁基锂的反应已被证明可以以良好到高产率生产环丙基苯基硫化物。通过用 2 当量的 1,3-双（苯硫基）丙烷处理 1-硫代环丙基苯硫醚，可以很容易地进行新的和方便的 1-硫代环丙基苯硫醚的原位制备。丁基锂在 0 °C 的 THF 中。与亲电子试剂的反应以良好的产率进行。O-芳基和O-烷基S-环丙基二硫代碳酸酯也可以高产率制备。1,2-双（苯硫基）乙烷在用丁基锂处理后转化为苯基乙烯基硫醚，而 1,4-双（苯硫基）丁烷则通过类似的处理方法原样回收。
• The reaction of β-stannyl carbonyl compounds with Lewis acids
  作者：Tadashi Sato、Masami Watanabe、Eigoro Murayama

  DOI：10.1016/s0040-4039(00)84330-0

  日期：1986.1

  β-Stannyl carbonyl compounds, when treated with Lewis acids, afforded cyclopropane derivatives or ketones, and the reaction was applied to the synthesis of β,γ-enones from α, β-enones.

  当用路易斯酸处理时，β-苯乙烯基羰基化合物可得到环丙烷衍生物或酮，并将该反应用于由α，β-烯酮合成β，γ-烯酮。
• A SIMPLE, HIGHLY VERSATILE SYNTHESIS OF CYCLOPROPYL PHENYL SULFIDES
  作者：Kazuhiko Tanaka、Hideki Uneme、Syuichi Matsui、Rikuhei Tanikaga、Aritsune Kaji

  DOI：10.1246/cl.1980.287

  日期：1980.3.5

  1,3-Bis(phenylthio)propane reacted readily with 2–2.2 equiv. of n-butyllithium in THF at 0°C to afford 1-lithiocyclopropyl phenyl sulfide. Treatment of the substituted 1,3-bis(phenylthio)propanes w...

  1,3-双（苯硫基）丙烷很容易与 2-2.2 当量反应。在 0°C 下在 THF 中溶解正丁基锂，​​得到 1-硫代环丙基苯基硫醚。处理取代的 1,3-双（苯硫基）丙烷...
• The Intramolecular Participation of Sulfide Linkage on the Reactivity of Carbenes and Diazoalkanes. II. Alkylcarbenes and Diazoalkanes Bearing Arylthio and Allylthio Groups on β-Carbon
  作者：Kiyosi Kondo、Iwao Ojima

  DOI：10.1246/bcsj.48.1490

  日期：1975.5

  β-Arylthio- and β-allylthioalkylcarbenes were generated from the corresponding ketones by a modification of the Bamford-Stevens method. Chemical evidence for the formation of novel cyclic ylides, i.e., thietanonium ylides, by an intramolecular electrophilic addition of the carbene to the sulfur atom was obtained. The resulting ylides underwent various types of rearrangements to afford cyclopropyl sulfides, thiaazulenes, thietanes, and/or tetrahydrothiophenes. The mechanisms and the relative amounts of the transition energies for these rearrangements are discussed. An intramolecular cycloaddition of β-allyl- and β-crotylthioalkyldiazoalkanes is also described. The final products of the reaction were 3-thiabicyclo[4.1.0]heptanes. A thiabicyclic pyrazoline, which is presumed to be an intermediate of the cycloaddition, could be isolated in the case of the thermal decomposition of 4-allylthio-4-methylpentan-2-one tosylhydrazone.

  通过改进 Bamford-Stevens 方法，从相应的酮生成 β-芳硫基-和 β-烯丙硫基烷基卡宾。获得了通过卡宾与硫原子的分子内亲电加成形成新型环状叶立德（即硫杂鎓叶立德）的化学证据。所得叶立德经历各种类型的重排，得到环丙基硫醚、噻薹、硫杂环丁烷和/或四氢噻吩。讨论了这些重排的机制和跃迁能的相对量。还描述了β-烯丙基-和β-巴豆基硫烷基重氮烷的分子内环加成。反应的最终产物是3-硫代双环[4.1.0]庚烷。硫代双环吡唑啉被认为是环加成的中间体，可以在4-烯丙硫基-4-甲基戊-2-酮甲苯磺酰腙热分解的情况下分离出来。
• Cohen, Theodore; Matz, James R., Synthetic Communications, 1980, vol. 10, # 4, p. 311 - 318
  作者：Cohen, Theodore、Matz, James R.

  DOI：——

  日期：——