2-deuterio-propionic acid methyl ester | 31590-69-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-deuterio-propionic acid methyl ester
• 英文别名: 2-Deuterio-propionsaeure-methylester；Propionsaeure-methylester；Methyl 2-deuteriopropanoate
• CAS: 31590-69-9
• 化学式: C₄H₈O₂
• 分子量: 89.0984
• InChiKey: RJUFJBKOKNCXHH-WFVSFCRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丙酸甲酯 在 乙醚 、 三苯甲基钠 作用下， 生成 2-deuterio-propionic acid methyl ester
  参考文献：
  名称：

  The Deuterium Isotope Effect of the Methanolysis of Some Organometallic Compounds

  摘要：

  DOI：

  10.1021/ja01627a057

文献信息

• A new mechanism for the photocleavage of monothioimides
  作者：Tai Y. Fu、John R. Scheffer、James Trotter

  DOI：10.1016/s0040-4039(00)76873-0

  日期：1994.5

  Based on solid state structure-reactivity correlation studies and on deuterium labeling experiments, it is concluded that the photochemical formation of thiobenzanilides 2a–d from monothioimides 1a–d does not involve initial γ-hydrogen atom abstraction as originally suggested in the literature. Alternative mechanistic possibilities are presented and discussed.

  基于固态结构-反应性相关性研究和氘标记实验，得出的结论是，单硫酰亚胺1a-d的硫代苯并甲腈2a-d的光化学形成不涉及最初的γ-氢原子抽象化。提出并讨论了替代的机械可能性。
• α-Methylenation of Methyl Propanoate by the Catalytic Dehydrogenation of Methanol
  作者：Patrizia Lorusso、Jacorien Coetzee、Graham R. Eastham、David J. Cole-Hamilton

  DOI：10.1002/cctc.201500763

  日期：2016.1

  one‐pot system for the conversion of methyl propanoate (MeP) to methyl methacrylate (MMA) has been investigated. In particular, this study is focused on the possibility of performing catalytic dehydrogenation of methanol for the in situ production of anhydrous formaldehyde, which is then consumed in a one‐pot base‐catalysed condensation with MeP to afford methyl 3‐hydroxy‐2‐methylpropanoate, which spontaneously

  已经研究了一种将丙酸甲酯（MeP）转化为甲基丙烯酸甲酯（MMA）的单锅系统。尤其是，这项研究的重点是进行甲醇催化脱氢以原位生产无水甲醛的可能性，然后将其在与MeP进行单锅碱催化缩合反应中消耗掉，得到3-羟基-2-甲基丙酸甲酯，它自发地脱氢为MMA，其中一些随后被氢化为2-甲基丙酸甲酯（M i Bu）。
• Deuterium labelling evidence for a hydride mechanism in the formation of methyl propanoate from carbon monoxide, ethene and methanol catalysed by a palladium complex
  作者：Graham R. Eastham、Robert P. Tooze、Melvyn Kilner、Douglas F. Foster、David J. Cole-Hamilton

  DOI：10.1039/b201514e

  日期：2002.4.9

  Reaction of ethene with CO in CH3OD in the presence of a catalyst prepared in situ from [Pd(DBPMB)(DBA)] (DBPMB = 1,2-bis[(di-tert-butyl)phosphinomethyl]benzene, DBA = dibenzylideneacetone) and methanesulfonic acid under conditions of good gas mixing gives a 1 ∶ 1 mixture of CH2DCH2CO2Me and CH3CHDCO2Me with no H incorporated into the CH3OD. If the gas mixing is less efficient, the methyl propanoate has 0–5 D atoms incorporated in the ethyl group, CH3OD exchanges to give increasing amounts of CH3OH throughout the reaction and there is a slight increase in the less deuteriated products with reaction time. Significant D incorporation into unreacted ethene is also observed. These results are interpreted in terms of a hydride mechanism with the rates of the individual steps under conditions of good mixing being: reversible H migration to coordinated ethene > CO coordination ≫ C2H4 exchange > H/D exchange.

  在由 [Pd(DBPMB)(DBA)] 原位制备的催化剂存在下，乙烯与 CO 在 CH3OD 中反应（DBPMB = 1,2-双[（二叔丁基）膦甲基]苯，DBA = 二亚苄基丙酮）与甲磺酸在良好气体混合的条件下得到CH2DCH2CO2Me和CH3CHDCO2Me的1∶1混合物，且CH3OD中没有掺入H。如果气体混合效率较低，则丙酸甲酯的乙基中会掺入 0-5 个 D 原子，CH3OD 在整个反应过程中会交换，产生越来越多的 CH3OH，并且随着反应时间的推移，氘化程度较低的产物会略有增加。还观察到 D 大量掺入未反应的乙烯中。这些结果根据氢化物机理进行解释，在良好混合的条件下各个步骤的速率为： 可逆的 H 迁移 配位乙烯>CO配位≫C2H4交换>H/D交换。
• The Deuterium Isotope Effect of the Methanolysis of Some Organometallic Compounds
  作者：Kenneth B. Wiberg

  DOI：10.1021/ja01627a057

  日期：1955.11