2-phenylethyl-1,1-d2-p-toluenesulfonate | 36809-05-9

• 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-phenylethyl-1,1-d2-p-toluenesulfonate
• 英文别名: toluene-4-sulfonic acid-(α,α-dideuterio-phenethyl ester)；Toluol-4-sulfonsaeure-(α,α-dideuterio-phenaethylester)；2-Phenyl-(1,1-d2)ethyl-p-toluolsulfonat；(1,1-dideuterio-2-phenylethyl) 4-methylbenzenesulfonate
• CAS: 36809-05-9
• 化学式: C₁₅H₁₆O₃S
• 分子量: 278.34
• InChiKey: CVPPUZPZPFOFPK-XUWBISKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-phenylethyl-1,1-d2-p-toluenesulfonate 在 platinum on activated charcoal 双氧水 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.5h， 生成 2-phenylethyldimethylamine-1,1-d2 oxide
  参考文献：
  名称：

  Smith, Peter James; Westaway, Kenneth Charles, Canadian Journal of Chemistry, 1987, vol. 65, p. 2149 - 2153

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酸甲酯 在 吡啶 、 lithium aluminium deuteride 作用下， 以 乙醚 为溶剂， 反应 2.5h， 生成 2-phenylethyl-1,1-d2-p-toluenesulfonate
  参考文献：
  名称：

  Smith, Peter James; Westaway, Kenneth Charles, Canadian Journal of Chemistry, 1987, vol. 65, p. 2149 - 2153

  摘要：

  DOI：

文献信息

• Substituent Effects. XVII. Rearrangement in the Acetolysis of 2-Arylethyl Tosylates
  作者：Mizue Fujio、Mutsuo Goto、Yoji Seki、Masaaki Mishima、Yuho Tsuno、Masami Sawada、Yoshio Takai

  DOI：10.1246/bcsj.60.1097

  日期：1987.3

  The label scrambling within the ethylene chain of the final acetolysis products was determined for a series of α-D2 labeled 2-arylethyl tosylates by using proton NMR spectroscopy and the kΔ⁄ks values were derived from the scrambling ratios. For both buffered and unbuffered acetolysis runs log (kΔ⁄ks) were not correlated linearly with σ° or σ+. Application of the LArSR Eq. results in linear correlations

  通过使用质子 NMR 光谱，确定了一系列 α-D2 标记的甲苯磺酸 2-芳基乙酯在最终乙酰化产物的乙烯链内的标记扰乱，kΔ⁄ks 值来自扰乱比。对于缓冲和未缓冲的乙酰化运行，日志 (kΔ⁄ks) 与 σ° 或 σ+ 不呈线性相关。LArSR 方程的应用。导致具有出色精度的线性相关性，对于无缓冲运行，log (kΔ⁄ks)=−3.70 (σ°+0.63Δ\barσR+)+0.152 和 log (kΔ⁄ks)=−3.97 (σ°+0.60Δ\barσR+) )−0.207 用于缓冲运行。芳基辅助途径的 ρΔ 和 rΔ 值是根​​据上述表观值估算的，这是基于 ks 途径的小 ρs 值的合理假设。
• Thermolysis of Phenethyl Phenyl Ether: A Model for Ether Linkages in Lignin and Low Rank Coal
  作者：Phillip F. Britt、A. C. III Buchanan、Elizabeth A. Malcolm

  DOI：10.1021/jo00125a044

  日期：1995.10

  The thermolysis of phenethyl phenyl ether (PPE) was studied at 330-425 degrees C to resolve the discrepancies in the reported mechanisms of this important model of the beta-ether linkage found in lignin and low rank coal. Cracking of PPE proceeded by two competitive pathways that produced styrene plus phenol and two previously undetected products, benzaldehyde plus toluene. The ratio of these pathways, defined as the alpha/beta selectivity, was 3.1 +/- 0.3 at 375 degrees C and independent of the PPE concentration. The kinetic order over ca. 10(3) variation in the initial concentration from the neat liquid, in solutions with biphenyl, and in the gas phase was 1.29 +/- 0.02. The rate expression for the decomposition in the liquid phase was log (k/M(-0.29) s(-1)) = (11.4 +/- 0.1) - (46.4 +/- 1.0)/2.303RT. The reaction could be accelerated by the addition of a free-radical initiator or a hydrogen bonding solvent, such as p-phenylphenol, but the product composition was altered with the latter. Thermolysis of PPE in tetralin, a model hydrogen donor solvent, increased the alpha/beta selectivity to 7 and accelerated the formation of secondary products. All the data was consistent with a free-radical chain mechanism for the decomposition of PPE. Styrene and phenol are produced by hydrogen abstraction at the alpha-carbon, beta-scission to form styrene and the phenoxy radical, followed by hydrogen abstraction. Benzaldehyde and toluene are formed by hydrogen abstraction at the beta-carbon, 1,2-phenyl migration from oxygen to carbon, beta-scission to form benzaldehyde, and the benzyl radical, followed by hydrogen abstraction. Thermochemical kinetic estimates indicate that product formation is controlled by the relative rate of hydrogen abstraction at the alpha- and beta-carbons by the phenoxy radical (dominant) and benzyl radical (minor) since beta-scission and 1,2-phenyl migration are fast relative to hydrogen abstraction. The electrophilic phenoxy radical has an inherently lower alpha/beta selectivity than the nonpolar benzyl radical because it benefits from the polar effects of the alpha-oxygen at the beta-carbon. The rate of the 1,2-phenyl migration was much faster than interconversion of 1-phenoxy-2-phenyl-1-ethyl radical and 1-phenoxy-2-phenyl-2-ethyl radical, and an activation barrier of <18 kcal mol(-1) was estimated for the 1,2-phenyl migration. Thermolysis of PhCD(2)CH(2)OPh and PhCH(2)CD(2)OPh was consistent with the previous results, indicating that there was no significant contribution of a concerted retro-ene pathway to the thermolysis of PPE.
• Su, Shiu-Chin H.; Wojcicki, Andrew, Organometallics, 1983, vol. 2, # 10, p. 1296 - 1301
  作者：Su, Shiu-Chin H.、Wojcicki, Andrew

  DOI：——

  日期：——
• LIGUORI, ANGELO;MASCARO, PAOLO;SINDONA, GIOVANNI;UCELLA, NICOLA, J. LABELL. COMPOUNDS AND RADIOPHARM., 28,(1990) N1, C. 1277-1283
  作者：LIGUORI, ANGELO、MASCARO, PAOLO、SINDONA, GIOVANNI、UCELLA, NICOLA

  DOI：——

  日期：——
• ETTINGER, MICHAEL D.;MAHASAY, SUMIT R.;STOCK, LEON M.;ZABRANSKY, ROBERT F+, ENERGY AND FUELS, 1,(1987) N 3, 274-279
  作者：ETTINGER, MICHAEL D.、MAHASAY, SUMIT R.、STOCK, LEON M.、ZABRANSKY, ROBERT F+

  DOI：——

  日期：——