4-(苯磺酰基)丁醛 | 114092-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(苯磺酰基)丁醛
• 英文名称: 4-(phenylsulfonyl)butyraldehyde
• 英文别名: 4-(Phenylsulfonyl)butanal；4-phenylsulphonylbutanal；4-phenylsulfonylbutanal；Butanal, 4-(phenylsulfonyl)-；4-(benzenesulfonyl)butanal
• CAS: 114092-92-1
• 化学式: C₁₀H₁₂O₃S
• 分子量: 212.269
• InChiKey: ZPTNAXBNXGWDMI-UHFFFAOYSA-N

物化性质

• 沸点：
  403.8±37.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(苯磺酰基)丁醛 在 哌啶 、 Lipase PS 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 169.0h， 生成 Acetic acid (E)-(R)-3-benzenesulfonyl-1-(2-benzenesulfonyl-ethyl)-allyl ester
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of .gamma.-hydroxy phenyl sulfones

  摘要：

  Lipase PS (from Pseudomonas cepacia) catalyzed the enantioselective transesterification of racemic gamma-hydroxy-alpha,beta-unsaturated phenyl sulfones 1 and their alpha,beta-saturated derivatives 3 with vinyl acetate in an organic solvent (usually (i)Pr2O). Remarkably, in substrates 1 with (E)-stereochemistry, the enantioselectivity of the process was little influenced by the nature of the R chain. Hence, very high enantiomeric ratios (E greater-than-or-equal-to 45) were observed in substrates 1 bearing short (R = Me or Et), long (R = n-Cr6H13 or n-C10H21), bulky (R = (i)Pr), or functionalized R chains. The (R)-enantiomer was the fast-reacting enantiomer in all cases. Concerning the reactivity, the rate of the reaction decreased significantly with an increase in size or length of the R chain (reaction time for 50% conversion from 3.5 to 162 h). Less satisfactory enantioselectivities (E = 5-48) were obtained when the saturated substrates 3 were used instead of the corresponding alpha,beta-unsaturated alcohols 1.

  DOI：

  10.1021/jo00040a028
• 作为产物：
  描述：

  苯甲砜 在 盐酸 、 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 22.25h， 生成 4-(苯磺酰基)丁醛
  参考文献：
  名称：

  Holmes, Andrew B.; Hughes, Andrew B.; Smith, Adrian L., Journal of the Chemical Society. Perkin transactions I, 1992, # 9, p. 1089 - 1100

  摘要：

  DOI：

文献信息

• Stereospecific synthesis of 2,3,6-trisubstituted piperidines: an efficient total synthesis of (.+-.)-pumiliotoxin C
  作者：Norman A. LeBel、N. Balasubramanian

  DOI：10.1021/ja00191a038

  日期：1989.4
• Asymmetric hydroformylations of sulfur-containing olefins catalyzed by BINAPHOS—Rh(I) complexes
  作者：Tetsuo Nanno、Nozomu Sakai、Kyoko Nozaki、Hidemasa Takaya

  DOI：10.1016/0957-4166(95)00339-q

  日期：1995.10

  Asymmetric hydroformylations of vinyl sulfides, allyl sulfides, and allyl sulfones catalyzed by (R,S)-BINAPHOS/Rh(acac)(CO)(2) afforded the corresponding branched oxo aldehydes as major products in 60-89% ee. Use of bulkier substituents on the sulfur in vinyl sulfides gave the branched oxo-aldehydes in higher regio- and enantioselectivities.
• Bury, Adrian; Earl, Harold A.; Stirling, Charles J. M., Journal of the Chemical Society. Perkin transactions II, 1987, p. 1281 - 1288
  作者：Bury, Adrian、Earl, Harold A.、Stirling, Charles J. M.

  DOI：——

  日期：——
• BURY, ADRIAN;EARL, HAROLD A.;STIRLING, CHARLES J. M., J. CHEM. SOC. PERKIN TRANS.,(1987) N 9, 1281-1287
  作者：BURY, ADRIAN、EARL, HAROLD A.、STIRLING, CHARLES J. M.

  DOI：——

  日期：——
• Lipase-catalyzed kinetic resolution of .gamma.-hydroxy phenyl sulfones
  作者：Juan C. Carretero、Esteban Dominguez

  DOI：10.1021/jo00040a028

  日期：1992.7

  Lipase PS (from Pseudomonas cepacia) catalyzed the enantioselective transesterification of racemic gamma-hydroxy-alpha,beta-unsaturated phenyl sulfones 1 and their alpha,beta-saturated derivatives 3 with vinyl acetate in an organic solvent (usually (i)Pr2O). Remarkably, in substrates 1 with (E)-stereochemistry, the enantioselectivity of the process was little influenced by the nature of the R chain. Hence, very high enantiomeric ratios (E greater-than-or-equal-to 45) were observed in substrates 1 bearing short (R = Me or Et), long (R = n-Cr6H13 or n-C10H21), bulky (R = (i)Pr), or functionalized R chains. The (R)-enantiomer was the fast-reacting enantiomer in all cases. Concerning the reactivity, the rate of the reaction decreased significantly with an increase in size or length of the R chain (reaction time for 50% conversion from 3.5 to 162 h). Less satisfactory enantioselectivities (E = 5-48) were obtained when the saturated substrates 3 were used instead of the corresponding alpha,beta-unsaturated alcohols 1.