propiolic acid-3-d | 18910-53-7

• 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: propiolic acid-3-d
• 英文别名: <3-2H>propiolic acid；Propiolsaeure-d1；3-deuterio-propynoic acid；3-Deuterioprop-2-ynoic acid
• CAS: 18910-53-7
• 化学式: C₃H₂O₂
• 分子量: 71.0397
• InChiKey: UORVCLMRJXCDCP-MICDWDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  propiolic acid-3-d 、 尿素 在 PPA 作用下， 反应 4.5h， 以49%的产率得到尿嘧啶-D1
  参考文献：
  名称：

  Mechanistic Studies of Antibody-Catalyzed Pyrimidine Dimer Photocleavage

  摘要：

  An antibody elicited against the trans, syn uracil cyclobutane dimer hapten 1 catalyzes the light-dependent cleavage of uracil dimers 1 and 2 to the corresponding monomers 3 and 4. Kinetic analysis of the antibody-catalyzed reaction affords a value of k(cat)/K-M = 1.7 x 10(3) M(-1) min(-1) for substrate 2, and comparison to the uncatalyzed reaction gives a rate acceleration of k(cat)/k(uncat) = 380. The wavelength dependence of the reaction and fluorescence quenching behavior suggest that a tryptophan residue is acting as a photosensitizer. The reaction mechanism was probed by measurement of secondary deuterium isotope effects. Substrates with selective deuterium substitutions in the cyclobutane ring were prepared, and isotope effects were measured by the method of internal competition using electrospray-ionization mass spectrometry to quantify the products. Kinetic isotope effects of (alpha-D)(V/K) = 1.11, 1.14, and 1.20 were observed for the 5,5'-, 6,6'-, and 5,5',6,6'-labeled substrates, respectively. These results are comparable to those observed in a similar study on the E. coli enzyme DNA photolyase(1) and suggest that the reaction may proceed via a radical anion intermediate with concerted breakage of the 5,5' and 6,6' bonds, Alternatively the reaction may proceed via a mechanism in which the first bond is cleaved in a reversible fashion.

  DOI：

  10.1021/ja00125a004
• 作为产物：
  描述：

  丙炔酸 在 重水 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 propiolic acid-3-d
  参考文献：
  名称：

  Mild Reaction Conditions for the Terminal Deuteration of Alkynes

  摘要：

  Routinely employed syntheses of terminally deuterated alkynes often utilize strong bases (i.e., LDA, n-BuLi, or Grignard reagents) or low (i.e., -78 degrees C) or elevated (i.e., 56 degrees C) reaction temperatures; furthermore many of these procedures afford average yields and in some cases less than optimum deuterium incorporation. Herein we report the application of alternative extremely mild reaction conditions that readily afford quantitative yields of terminally deuterated alkynes in a matter of minutes with exceptional isotope incorporation at ambient temperature.

  DOI：

  10.1021/ol2029178

文献信息

• Biosynthetic studies on ansatrienin A. Formation of the cyclohexanecarboxylic acid moiety
  作者：Bradley S. Moore、Hyeongjin Cho、Rosangela Casati、Eileen Kennedy、Kevin A. Reynolds、Ursula Mocek、John M. Beale、Heinz G. Floss

  DOI：10.1021/ja00065a042

  日期：1993.6

  biosynthesis of ansatrienin (mycotrienin) has been studied. [sup 13]C- and [sup 2]H-labeled samples of shikimic acid were used to probe the stereochemistry of processing the cyclohexane ring of shikimic acid and to establish the fate of all the precursor hydrogens in this transformation. A sample of [2-[sup 13]C]shikimic acid was fed to Streptomyces collinus Tu 1982, and [sup 13]C in the resulting ansatrienin

  环己烷甲酸部分在 ansatrienin (mycotrienin) 的生物合成中的形成已被研究。[sup 13]C-和[sup 2]H-标记的莽草酸样品用于探测处理莽草酸环己烷环的立体化学，并确定该转化中所有前体氢的命运。[2-[sup 13]C]莽草酸样品被加入 Streptomyces collinus Tu 1982，发现所得 ansatrienin 中的 [sup 13]C 仅位于 C-36。在 Ansatrienin 的生物合成样品的水解中，伴随环己烷甲酸的 1-环己烯甲酸在 C-2 处而不是在 C-6 处带有 [sup 13] C 标记。[2-[sup 2]H]-、[3-[sup 2]H]-、[4-[sup 2]H]、[2,5-[sup 2]H[sub 2]]-的样本, [2,3,4,5-[sup 2]H[sub 4]]-, 和[6-[sup 2]H[sub 1]]莽草酸被喂给S
• 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：——
• SIMCHEN G.; ENTENMANN G., J. LIEBIGS ANN. CHEM., 1977, NO 8, 1249-1266
  作者：SIMCHEN G.、 ENTENMANN G.

  DOI：——

  日期：——