2-氧代乙烷磺酸 | 32797-12-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: 2-氧代乙烷磺酸
• 英文名称: 2-oxo-ethanesulfonic acid
• 英文别名: 2-Oxo-aethansulfonsaeure；Acetaldehydsulfonsaeure；Sulfoacetaldehyd；acetaldehydesulfonic acid；Sulfoacetaldehyde；2-oxoethanesulfonic acid
• CAS: 32797-12-9
• 化学式: C₂H₄O₄S
• 分子量: 124.117
• InChiKey: JTJIXCMSHWPJJE-UHFFFAOYSA-N

物化性质

• 密度：
  1.603±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2914190090

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 、 barium(II) chloride 作用下， 生成 2-氧代乙烷磺酸
  参考文献：
  名称：

  磺基喹诺酮糖及其醛糖酸：高碘酸盐的制备及氧化为2-磺基乙醛

  摘要：

  摘要制备了6-脱氧-6-C-磺基-d-吡喃葡萄糖（磺基古诺糖），并以其铍盐和钾盐为特征。还获得了其醛酸的双环己基铵盐，即6-脱氧-6-C-磺基-d-葡萄糖酸。它们被高碘酸钠氧化得到2-磺基乙醛。

  DOI：

  10.1016/s0008-6215(97)00112-2

文献信息

• Schroeter, Justus Liebigs Annalen der Chemie, 1919, vol. 418, p. 248
  作者：Schroeter

  DOI：——

  日期：——
• Terentjew; Janowskaja, Zhurnal Obshchei Khimii, 1953, vol. 23, p. 620
  作者：Terentjew、Janowskaja

  DOI：——

  日期：——
• Terent'ew et al., Zhurnal Obshchei Khimii, 1953, vol. 23, p. 746,752;engl.Ausg.S.779,783
  作者：Terent'ew et al.

  DOI：——

  日期：——
• Kinetics and mechanism of aliphatic amine oxidation by aqueous (batho)2CuII
  作者：Fengjiang Wang、Lawrence M. Sayre

  DOI：10.1021/ja00027a032

  日期：1992.1

  The kinetics of oxidation of a large series of aliphatic amines by the 'high-potential'' oxidant (batho)2Cu(II) (batho = 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrolinedisulfonate) was studied under pseudo-first-order conditions (excess amine) in water or in 30% aqueous methanol (v/v) at 25-degrees-C over the pH range 7-11. The oxidations follow bell-shaped pH-rate profiles, with the low-pH leg reflecting the fact that only the free amine base is subject to oxidation and the high-pH leg representing conversion of (batho)2Cu(II) to an ineffective oxidant at high pH. The latter is thought to be (batho)Cu(II)(OH2)OH on the basis of the observed effect of [batho] on rate at high pH, and curve fitting of the rate data yielded estimates of the unitless K(eq) values governing this conversion. The variation in rate with degree of N-substitution and other structure-reactivity trends (such as the effect of ring size and the non-rate-retarding effect of 2,4,6-trimethyl substitution on PhCH2NR2) support a mechanism involving initial outer-sphere one-electron transfer, followed by proton transfer to the solvent, and then a rapid second one-electron oxidation to give imine/iminium product. Inner-sphere coordination of chelating amines shuts down the redox reaction, presumably as a consequence of displacement of the batho ligand(s) needed for high oxidant strength. Deuterium kinetic isotope effect (DKIE) measurements (i) comparing PhCD2N(CD3)2 vs PhCH2N(CH3)2 (intermolecular DKIE) and (ii) determining N-dealkylation preference in the case of PhCH2N(CH3)CD2Ph (intramolecular DKIE) suggest that the initial electron transfer is mainly rate-limiting. A rate comparison between erythro and three diastereomers of 1,2-diphenyl-2-piperidinoethanol indicates a stereoelectronic preference for one-electron oxidation at nitrogen when held antiperiplanar to a beta-hydroxyl. Stoichiometry studies using an excess of the Cu(II) oxidant reveal regioselective and chemoselective factors governing the overall amine-to-iminium oxidations.
• Terentjew; Wolynski, Zhurnal Obshchei Khimii, 1949, vol. 19, p. 785
  作者：Terentjew、Wolynski

  DOI：——

  日期：——