N-[(2R)-2-(2,4-dichlorophenyl)-2-sulfanylethyl]acetamide | 1165796-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(2R)-2-(2,4-dichlorophenyl)-2-sulfanylethyl]acetamide
• CAS: 1165796-81-5
• 化学式: C₁₀H₁₁Cl₂NOS
• 分子量: 264.175
• InChiKey: WBBMXPIXGFQUIW-JTQLQIEISA-N

物化性质

• 沸点：
  448.3±45.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(2R)-2-(2,4-dichlorophenyl)-2-sulfanylethyl]acetamide 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 (R)-2-((4-chlorobenzyl)thio)-2-(2,4-dichlorophenyl)ethanamine
  参考文献：
  名称：

  Enantio- and diastereoselective addition of thioacetic acid to nitroalkenes via N-sulfinyl urea catalysis

  摘要：

  The enantioselective addition of thioacetic acid to nitroalkenes was achieved using N-sulfinyl urea catalysis. In this report, the scope of the reaction was extended to the enantio- and diastereoselective thioacetic acid addition to cyclic alpha,beta-disubstituted nitroalkenes. Additionally, the role of the sulfinyl group was investigated by replacing it with a variety of aryl and sulfonyl groups. Of 15 urea catalysts synthesized and tested, none displayed comparable selectivity to the sulfinyl catalysts, highlighting the importance of the sulfinyl group in attaining high enantioselectivity in the thioacetic acid addition. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.048
• 作为产物：
  描述：

  1-acetylthio-1-(2,4-dichlorophenyl)-2-nitroethane 在 盐酸 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以74%的产率得到N-[(2R)-2-(2,4-dichlorophenyl)-2-sulfanylethyl]acetamide
  参考文献：
  名称：

  N-亚磺酰基脲有机催化对硝基烯烃与硫代乙酸的对映选择性加成

  摘要：

  描述了使用新的亚磺酰基脲有机催化剂将硫代乙酸高度对映选择性加成到硝基烯烃。对于各种芳香族和脂肪族硝基烯烃底物，硫代乙酸的添加以高产率和对映选择性进行。这种新方法可用于制备手性 1,2-氨基硫醇衍生物，正如临床使用的抗真菌药物磺康唑的首次对映选择性合成所证明的那样。

  DOI：

  10.1021/ja903351a

文献信息

• Enantioselective Addition of Thioacetic Acid to Nitroalkenes via <i>N</i>-Sulfinyl Urea Organocatalysis
  作者：Kyle L. Kimmel、MaryAnn T. Robak、Jonathan A. Ellman

  DOI：10.1021/ja903351a

  日期：2009.7.1

  The highly enantioselective addition of thioacetic acid to nitroalkenes using a new sulfinyl urea organocatalyst is described. The addition of thioacetic acid proceeds in high yields and enantioselectivities for a variety of aromatic and aliphatic nitroalkene substrates. This new method is useful for preparing chiral 1,2-aminothiol derivatives, as demonstrated by the first enantioselective synthesis

  描述了使用新的亚磺酰基脲有机催化剂将硫代乙酸高度对映选择性加成到硝基烯烃。对于各种芳香族和脂肪族硝基烯烃底物，硫代乙酸的添加以高产率和对映选择性进行。这种新方法可用于制备手性 1,2-氨基硫醇衍生物，正如临床使用的抗真菌药物磺康唑的首次对映选择性合成所证明的那样。
• Enantio- and diastereoselective addition of thioacetic acid to nitroalkenes via N-sulfinyl urea catalysis
  作者：Kyle L. Kimmel、MaryAnn T. Robak、Stephen Thomas、Melissa Lee、Jonathan A. Ellman

  DOI：10.1016/j.tet.2012.01.048

  日期：2012.3

  The enantioselective addition of thioacetic acid to nitroalkenes was achieved using N-sulfinyl urea catalysis. In this report, the scope of the reaction was extended to the enantio- and diastereoselective thioacetic acid addition to cyclic alpha,beta-disubstituted nitroalkenes. Additionally, the role of the sulfinyl group was investigated by replacing it with a variety of aryl and sulfonyl groups. Of 15 urea catalysts synthesized and tested, none displayed comparable selectivity to the sulfinyl catalysts, highlighting the importance of the sulfinyl group in attaining high enantioselectivity in the thioacetic acid addition. (C) 2012 Elsevier Ltd. All rights reserved.