2-methylcyclopentanone-2,5,5-d3 | 52291-17-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methylcyclopentanone-2,5,5-d3
• 英文别名: 2,6,6-trideuterio-2-methyl-cyclopentanone；1-Methyl-1.3.3-trideutero-cyclopentanon-(2)；2,5,5-d3-2-Methylcyclopentanon；2-Methylcyclopentanone (2,5,5-D3)；2,2,5-trideuterio-5-methylcyclopentan-1-one
• CAS: 52291-17-5
• 化学式: C₆H₁₀O
• 分子量: 101.121
• InChiKey: ZIXLDMFVRPABBX-AFBAWBIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methylcyclopentanone-2,5,5-d3 在 L-Selectride 作用下， 生成 cis-2-methylcyclopentanol-2,5,5-d3
  参考文献：
  名称：

  Hydrogen participation in the solvolysis of 2-methylcyclopentyl arenesulfonates

  摘要：

  Solvolysis of cis- and trans-2-methylcyclopentyl arenesulfonates has been examined in several ethanol-water, trifluoroethanol-water, and hexafluoroisopropyl alcohol-water mixtures. Rates, alpha-d and beta-d kinetic isotope effects, and product yields have been determined. The results indicate that cis-2-methylcyclopentyl p-toluenesulfonate reacts with rate-determining hydrogen participation after reversible formation of the intimate ion pair. In contrast, trans-2-methylcyclopentyl p-bromobenzenesulfonate reacts by varying proportions of rate-determining solvent nucleophilic attack, solvent-promoted elimination, and ion pair separation after reversible formation of the intimate ion pair. The details of these mechanisms are quantitatively described with the aid of a steady state analysis, and the results are correlated with the mechanisms previously proposed for cyclopentyl brosylate and 2,2-dimethylcyclopentyl brosylate.

  DOI：

  10.1021/jo00011a019
• 作为产物：
  描述：

  2-甲基环戊酮 在 重水 、 sodium 作用下， 生成 2-methylcyclopentanone-2,5,5-d3
  参考文献：
  名称：

  Hydrogen participation in the solvolysis of 2-methylcyclopentyl arenesulfonates

  摘要：

  Solvolysis of cis- and trans-2-methylcyclopentyl arenesulfonates has been examined in several ethanol-water, trifluoroethanol-water, and hexafluoroisopropyl alcohol-water mixtures. Rates, alpha-d and beta-d kinetic isotope effects, and product yields have been determined. The results indicate that cis-2-methylcyclopentyl p-toluenesulfonate reacts with rate-determining hydrogen participation after reversible formation of the intimate ion pair. In contrast, trans-2-methylcyclopentyl p-bromobenzenesulfonate reacts by varying proportions of rate-determining solvent nucleophilic attack, solvent-promoted elimination, and ion pair separation after reversible formation of the intimate ion pair. The details of these mechanisms are quantitatively described with the aid of a steady state analysis, and the results are correlated with the mechanisms previously proposed for cyclopentyl brosylate and 2,2-dimethylcyclopentyl brosylate.

  DOI：

  10.1021/jo00011a019

文献信息

• IONIZABLE ISOTOPIC LABELING REAGENTS FOR RELATIVE QUANTIFICATION BY MASS SPECTROMETRY
  申请人：SMITH Lloyd M.

  公开号：US20120022230A1

  公开（公告）日：2012-01-26

  Relative quantification of metabolites by Electrospray Ionization Mass Spectrometry (ESI-MS) requiring a mechanism for simultaneous analysis of multiple analytes in two or more samples. Labeling reagents that are reactive to particular compound classes and differ only in their isotopic compositions facilitate relative quantification. Heavy and light isotopic forms of methylacetimidate were synthesized and used as labeling reagents for quantification of amine-containing molecules. Heavy and light isotopic forms of formaldehyde and cholamine were also synthesized and used independently as labeling reagents for quantification of amine-containing and carboxylic acid-containing molecules, such as found in biological samples. The labeled end-products are positively charged under normal acidic conditions involving conventional Liquid Chromatography Mass Spectrometry (LC/MS) applications. Labeled primary and secondary amine and carboxylic acid end-products generated higher signals concerning mass-spectra than pre-cursor molecules and improved sensitivity. Improved accuracy concerning relative quantification was demonstrated by mixing heavy and light labeled Arabidopsis extracts in different ratios.
• US8563777B2
  申请人：——

  公开号：US8563777B2

  公开（公告）日：2013-10-22
• Hydrogen participation in the solvolysis of 2-methylcyclopentyl arenesulfonates
  作者：Michael A. Imhoff、R. Michael Ragain、Kimberly Moore、V. J. Shiner

  DOI：10.1021/jo00011a019

  日期：1991.5

  Solvolysis of cis- and trans-2-methylcyclopentyl arenesulfonates has been examined in several ethanol-water, trifluoroethanol-water, and hexafluoroisopropyl alcohol-water mixtures. Rates, alpha-d and beta-d kinetic isotope effects, and product yields have been determined. The results indicate that cis-2-methylcyclopentyl p-toluenesulfonate reacts with rate-determining hydrogen participation after reversible formation of the intimate ion pair. In contrast, trans-2-methylcyclopentyl p-bromobenzenesulfonate reacts by varying proportions of rate-determining solvent nucleophilic attack, solvent-promoted elimination, and ion pair separation after reversible formation of the intimate ion pair. The details of these mechanisms are quantitatively described with the aid of a steady state analysis, and the results are correlated with the mechanisms previously proposed for cyclopentyl brosylate and 2,2-dimethylcyclopentyl brosylate.