2-(4'-methylthiophenyl)propan-2-ol | 82955-01-9

• 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: 2-(4'-methylthiophenyl)propan-2-ol
• 英文别名: 2-[4-(Methylthio)phenyl]-2-propanol；2-(4-methylsulfanylphenyl)propan-2-ol
• CAS: 82955-01-9
• 化学式: C₁₀H₁₄OS
• 分子量: 182.287
• InChiKey: CFXFRIBPANBRQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4'-methylthiophenyl)propan-2-ol 在 盐酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.03h， 生成 1-(1-Chloro-1-methyl-ethyl)-4-methanesulfinyl-benzene
  参考文献：
  名称：

  α-磺酰基和α-亚磺酰基碳正离子的溶剂分解生成

  摘要：

  ArC(CH 3 )(SO 2 Ph)OMs 和 α-溴亚硫酸盐 ArC(CH 3 )(SO 2 Ph)Br 的溶剂解脱甲磺酸盐的练习曲。L'ordre de reactiverelative lors de la solvolyse des substrats du type p-CH 3 C 6 H 4 C(CH 3 )BrE, ou E est un groupe electronegatif, est COPh>PO(OEt) 2 >CN>SOPh>CF 3 >SO 2 Ph

  DOI：

  10.1021/ja00242a031
• 作为产物：
  描述：

  4-(甲基硫代)苯甲酸甲酯 在 甲基碘化镁 、 乙醚 作用下， 生成 2-(4'-methylthiophenyl)propan-2-ol
  参考文献：
  名称：

  Rates of Solvolysis of the m- and p-Phenyl-, m- and p-Methylthio-, and m- and p- Trimethylsilylphenyldimethylcarbinyl Chlorides. Steric Inhibition of Resonance as a Factor in Electrophilic Substituent Constants^1,2

  摘要：

  DOI：

  10.1021/ja01551a051

文献信息

• Kinetics and Mechanism of Acid Catalysed Hydration of α-Methylstyrenes
  作者：Oldřich Pytela、Bronislav Trlida

  DOI：10.1135/cccc20071025

  日期：——

  Twelve para-substituted α-methylstyrenes with substituents H, CH₃, CF₃, CH₃O, CH₃S, F, Cl, Br, CH₃CO, CH₃SO₂, CN a NO₂ were synthesised; additionally, the acid catalysed hydration kinetics of these compounds were measured in sulfuric acid in a concentration range c from 0.017 to 9.58 mol l^-1, at 25.0 °C. The observed rate constants obtained were used to construct the kinetic acidity function and calculate the catalytic rate constants. Based on the evaluation of the acidity function kinetic dependence on acid medium concentration, and the substituent effects of acid catalysed hydration of α-methylstyrenes on the catalytic rate constants, the mechanism of acid catalysed hydration was verified. The mechanism involves the addition of a proton to the double bond of α-methylstyrene in the rate-limiting reaction step denoted as A-SE2. No evident difference was found between the effects of the acid medium on the acid catalysed hydration of styrenes and α-methylstyrenes, which indicates very similar activity coefficients of the reactants, and of the transition state of both substrates. The substituent effects evaluation shows that the rate-limiting step of the reaction consists in the addition of a proton to the substrate. The carbocation formation in the transition state of this reaction step proceeds roughly half-way compared with the extent of the carbocation formation by cumyl chloride hydrolysis. The obtained carbocation is in particular stabilised by the substituents with +M effect, while the influence of the substituents with -M and I effects is significantly smaller.

  十二种带有取代基H、CH₃、CF₃、CH₃O、CH₃S、F、Cl、Br、CH₃CO、CH₃SO₂、CN和NO₂的α-甲基苯乙烯被合成；此外，在浓度范围从0.017到9.58摩尔/升的硫酸中，测量了这些化合物的酸催化水合动力学。所得到的观察速率常数被用来构建动力学酸度函数并计算催化速率常数。通过评估酸性函数动力学对酸性介质浓度的依赖性，以及α-甲基苯乙烯的酸催化水合反应的取代基效应对催化速率常数的影响，验证了酸催化水合的机理。该机理涉及在速率限制的反应步骤中向α-甲基苯乙烯的双键加入质子，被标记为A-SE2。在酸性介质对苯乙烯和α-甲基苯乙烯的酸催化水合的影响之间没有明显差异，这表明反应物和两种底物的过渡态的活性系数非常相似。取代基效应评估显示，反应的速率限制步骤在向底物加入质子时发生。与叔丁基氯化物水解形成的碳正离子相比，该反应步骤的过渡态中的碳正离子形成大致进行了一半。所得到的碳正离子特别受到具有+M效应的取代基的稳定作用，而具有-M和I效应的取代基的影响则明显较小。
• Copper catalyzed direct C–H double methylation of aromatic aldehydes employing methanol as an alkylating agent
  作者：Sereena Sunny、Ramasamy Karvembu

  DOI：10.1039/d4gc02415j

  日期：——

  A mild sustainable protocol for the direct C–H double methylation of aromatic aldehydes has been accomplished by using un-activated methanol as a C1 source. Readily available, inexpensive copper sulfate has been utilized as a greener catalyst at room temperature. This methodology represents the first example of direct synthesis of tertiary alcohols from aromatic aldehydes operating via a concerted

  通过使用未活化的甲醇作为 C 1源，已经完成了芳香醛直接 C-H 双甲基化的温和可持续方案。容易获得且廉价的硫酸铜已被用作室温下的绿色催化剂。该方法代表了通过协同自由基介导途径消除 H 2 O 2从芳香醛直接合成叔醇的第一个例子。该产品的克级合成成功表明了该方案在工业应用中的可行性。
• Richard, John P.; Jagannadham, Vandannapu; Amyes, Tina L., Journal of the American Chemical Society, 1994, vol. 116, # 15, p. 6706 - 6712
  作者：Richard, John P.、Jagannadham, Vandannapu、Amyes, Tina L.、Mishima, Masaaki、Tsuno, Yuho

  DOI：——

  日期：——
• Giansiracusa, Joseph J.; Jenkins, Margot J.; Kelly, David P., Australian Journal of Chemistry, 1982, vol. 35, # 2, p. 443 - 450
  作者：Giansiracusa, Joseph J.、Jenkins, Margot J.、Kelly, David P.

  DOI：——

  日期：——