diethyl [2,3-D₂]succinate | 35525-83-8

• 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: diethyl [2,3-D₂]succinate
• 英文别名: dl-diethyl-2,3-dideuteriosuccinate；2,3-dideuterio-succinic acid diethyl ester；2,3-Dideuterio-bernsteinsaeure-diaethylester；racem.-2,3-Dideuterosuccinat；Diethyl 2,3-dideuteriobutanedioate
• CAS: 35525-83-8
• 化学式: C₈H₁₄O₄
• 分子量: 176.181
• InChiKey: DKMROQRQHGEIOW-KCZCTXNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl [2,3-D₂]succinate 在 lithium aluminium tetrahydride 作用下， 以7.2 g的产率得到dl-dideuteriobutane-1,4-diol
  参考文献：
  名称：

  Vibrational circular dichroism study of (2S,3S)-dideuteriobutyrolactone. Synthesis, normal mode analysis, and comparison of experimental and calculated spectra

  摘要：

  The preparation, characterization, infrared absorption, and vibrational circular dichroism (VCD) spectra of the title compound are presented. From ab initio quantum mechanical energy minimization, geometry optimization calculations, the lowest energy conformation is a slightly distorted envelope form, so that deuteration give rise to both pseudoaxially and pseudoequatorially substituted conformers. The vibrational spectra (IR and Raman) have been assigned by comparison of frequencies and overall intensity patterns to those calculated by using an ab initio force field obtained for both conformers. This force field was subsequently modified by refining scale factors to improve the fit to frequencies of assigned bands for both the d0 and d2 isotopomers. The absorption intensities and VCD signs and magnitudes were calculated by the ab initio magnetic field perturbation theory of Stephens using the distributed origin gauge with origins at the nuclei. Good qualitative agreement was found between the experimental and theoretical dipole strengths and rotational strengths when the average of the calculated values for the two conformers was used. The best calculations used a 6-31G** basis set for for the force field and the intensities, but the refined force field did not lead to a significant improvement in the intensity or VCD pattern (other than frequency alignment) as compared to the unscaled ab initio result. For purposes of comparison to previous reports, calculations were also made for the planar conformation. Test calculations with variants of more approximate methods that do not allow for charge reorganization associated with nuclear motion gave distinctly unsatisfactory results, particularly in the mid-infrared portion of the spectrum.

  DOI：

  10.1021/j100204a012
• 作为产物：
  描述：

  富马酸二乙酯 在 platinum(IV) oxide 、 acetic acid ester 、 氘 作用下， 生成 diethyl [2,3-D₂]succinate
  参考文献：
  名称：

  Succinic-α-d,α'-d Acid and its Derivatives. II. Stereochemistry of the Type RR'CHD

  摘要：

  DOI：

  10.1021/ja01300a011

文献信息

• Reduction of Activated Alkenes by P ^III /P ^V Redox Cycling Catalysis
  作者：Lars Longwitz、Thomas Werner

  DOI：10.1002/anie.201912991

  日期：2020.2.10

  using a phosphetane oxide catalyst in the presence of a simple organosilane as the terminal reductant and water as the hydrogen source. Quantitative hydrogenation was observed when 1.0 mol % of a methyl‐substituted phosphetane oxide was employed as the catalyst. The procedure is highly selective towards activated double bonds, tolerating a variety of functional groups that are usually prone to reduction

  在简单的有机硅烷作为末端还原剂和水作为氢源的情况下，使用氧化膦催化剂可以轻松地还原不饱和羰基化合物的碳-碳双键。当使用1.0 mol％的甲基取代的氧化膦作为催化剂时，可以观察到定量氢化。该方法对活化的双键具有高度选择性，可以耐受通常易于还原的各种官能团。总共将25个烯烃和两个炔烃氢化成相应的烷烃，产率高达99％。值得注意的是，活性较低的聚（甲基氢硅氧烷）也可以用作末端还原剂。
• A convenient method for palladium-catalyzed reductive deuteration of organic substrates using deuterated hypophosphite in D₂O
  作者：Makoto Oba

  DOI：10.1002/jlcr.3277

  日期：2015.5.15

  A convenient method for the deuteration of organic substrates using deuterated hypophosphite as the deuterium source was investigated. Transfer deuteration of organic substrates, such as aromatic halides, alkenes, alkynes, epoxides, and O-benzyl derivatives, in the presence of palladium on carbon in deuterium oxide proceeded efficiently to give the corresponding deuterated products in excellent yields with high deuterium contents.

  我们研究了一种使用氘化次亚磷酸酯作为氘源对有机底物进行氘化的简便方法。在氧化氘中的碳上钯存在下，芳香卤化物、烯烃、炔烃、环氧化物和 O-苄基衍生物等有机底物的转移氘化过程高效进行，并以极高的氘含量得到相应的氘化产物。
• Erlenmeyer; Schoenauer; Suellmann, Helvetica Chimica Acta, 1936, vol. 19, p. 1377
  作者：Erlenmeyer、Schoenauer、Suellmann

  DOI：——

  日期：——
• HILL, R. K.;LEDFORD, N. D.;RENBAUM, L. A., J. LABELLED COMPOUNDS AND RADIOPHARM., 1985, 22, N 2, 143-148
  作者：HILL, R. K.、LEDFORD, N. D.、RENBAUM, L. A.

  DOI：——

  日期：——