己二酸-d10 | 25373-21-1

• 物质功能分类: 化学试剂 - 氘代试剂
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 己二酸-d10
• 中文别名: 肥酸-D10
• 英文名称: adipic acid d-10
• 英文别名: adipic-d8 acid-d2；D₁₀-adipic acid；Adipinsaeure-d(10)；decadeuterio-hexanedioic acid；Decadeuterio-adipinsaeure；decadeuterio-adipic acid；Adipic acid-d10；dideuterio 2,2,3,3,4,4,5,5-octadeuteriohexanedioate
• CAS: 25373-21-1
• 化学式: C₆H₁₀O₄
• 分子量: 156.064
• InChiKey: WNLRTRBMVRJNCN-YQMDOBQVSA-N

物化性质

• 熔点：
  151-154 °C(lit.)
• 沸点：
  265 °C100 mm Hg(lit.)
• 闪点：
  385 °F
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R20/22
• WGK Germany：
  1

制备方法与用途

肥酸-D10是一种氘代物质，而肥酸则是生产尼龙的重要前体。

反应信息

• 作为反应物：
  描述：

  己二酸-d10 在 水 作用下， 生成 己二酸-D8
  参考文献：
  名称：

  Susi, Spectrochimica Acta, 1959, vol. 15, p. 1063,1067

  摘要：

  DOI：

文献信息

• Dynamic NMR Study of the Tautomerism of Bicyclic Oxalamidines: Kinetic HH/HD/DD Isotope and Solvent Effects
  作者：Gerd Scherer、Hans-Heinrich Limbach

  DOI：10.1021/ja00083a009

  日期：1994.2

  be labeled with 15 N and partly with 2 H. The tautomerism of OA6 was too slow to be detectable by NMR, in contrast to the case of OA7. Rate constants of the tautomerism of OA7 dissolved in methylcycloherane-d 14 (MCY) and in acetonitrile d 3 (AN) could be obtained, including the full kinetic HH/HD/DD isotope effects

  已通过动态核磁共振光谱研究了由氮原子之间的分子内简并双质子转移组成的奥拉脒的互变异构现象。对两种双环口服脒进行了实验，即 2,2'-双（3,4,5,6-四氢-1,3-二嗪）（OA6）和 2,2'-双（4,5,6,7-四氢-1,3-二氮杂) (OA7) 溶于有机溶剂。为此，两种化合物都必须用 15 N 和部分用 2 H 标记。与 OA7 的情况相比，OA6 的互变异构太慢而无法通过 NMR 检测到。可以获得溶解在甲基环醚-d 14 (MCY) 和乙腈 d 3 (AN) 中的 OA7 互变异构的速率常数，包括完整的动力学 HH/HD/DD 同位素效应
• Strong Experimental Evidence of CH···O Hydrogen Bonds in Cyclopentanone:  The Splitting of the ν(CO) Mode Revisited
  作者：Pedro D. Vaz、Paulo J. A. Ribeiro-Claro

  DOI：10.1021/jp034568g

  日期：2003.8.1

  The assignment of the splitting of the ν(CO) mode in cyclopentanone is reassessed through an extensive vibrational study, including temperature and solvent variation studies, isotopic substitution, and ab initio calculations of monomer and dimer structures and spectra. The results show that the assignment of the splitting of the ν(CO) mode to Fermi resonance is based on several of erroneous observations

  通过广泛的振动研究，包括温度和溶剂变化研究、同位素取代以及单体和二聚体结构和光谱的从头计算，重新评估了环戊酮中 ν(CO) 模式的分裂分配。结果表明，将ν(CO)模式的分裂分配给费米共振是基于几个错误的观察结果，并提供了通过CH···O氢键进行分子缔合的强有力的实验证据。
• Cross-Dehydrogenative Couplings between Indoles and β-Keto Esters: Ligand-Assisted Ligand Tautomerization and Dehydrogenation via a Proton-Assisted Electron Transfer to Pd(II)
  作者：Mikko V. Leskinen、Ádám Madarász、Kai-Tai Yip、Aini Vuorinen、Imre Pápai、Antti J. Neuvonen、Petri M. Pihko

  DOI：10.1021/ja501681y

  日期：2014.4.30

  Cross-dehydrogenative coupling reactions between beta-ketoesters and electron-rich arenes, such as indoles, proceed with high regiochemical fidelity with a range of beta-ketoesters and indoles. The mechanism of the reaction between a prototypical beta-ketoester, ethyl 2-oxocyclopentanonecarboxylate, and N-methylindole has been studied experimentally by monitoring the temporal course of the reaction by H-1 NMR, kinetic isotope effect studies, and control experiments. DFT calculations have been carried out using a dispersion-corrected range-separated hybrid functional (omega B97X-D) to explore the basic elementary steps of the catalytic cycle. The experimental results indicate that the reaction proceeds via two catalytic cycles. Cycle A, the dehydrogenation cycle, produces an enone intermediate. The dehydrogenation is assisted by N-methylindole, which acts as a ligand for Pd(II). The computational studies agree with this conclusion, and identify the turnover-limiting step of the dehydrogenation step, which involves a change in the coordination mode of the beta-keto ester ligand from an O,O'-chelate to an beta'-bound Pd enolate. This ligand tautomerization event is assisted by the if-bound indole ligand. Subsequent scission of the beta'-C-H bond takes place via a proton-assisted electron transfer mechanism, where Pd(II) acts as an electron sink and the trifluoroacetate ligand acts as a proton acceptor, to produce the Pd(0) complex' of the enone intermediate. The coupling is completed in cycle B, where the enone is coupled with indole. Pd(TFA)(2) and TFA-catalyzed pathways were examined experimentally and computationally for this cycle, and both were found to be viable routes for the coupling step.
• Susi, Spectrochimica Acta, 1959, vol. 15, p. 1063,1067
  作者：Susi

  DOI：——

  日期：——