1-acetylthio-1-phenyl-2-nitropropane | 1669-27-8

• 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: 1-acetylthio-1-phenyl-2-nitropropane
• 英文别名: 2-Nitro-1-acetylmercapto-1-phenyl-propan；S-(2-nitro-1-phenylpropyl) ethanethioate
• CAS: 1669-27-8
• 化学式: C₁₁H₁₃NO₃S
• 分子量: 239.295
• InChiKey: BTAUDCYZWXUCOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  88.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯,(2-硝基-1-丙烯基)-,(E)- 、 硫代乙酸 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 1-acetylthio-1-phenyl-2-nitropropane
  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

文献信息

• Potential Antiradiation Compounds II. Extension of the Nitro-Thiolacetate Route
  作者：K. Venkatramana Bhat、Walter C. McCarthy

  DOI：10.1002/jps.2600531231

  日期：1964.12

  roethane which was reduced with lithium aluminum hydride to produce 1-(3′,4′-methylenedioxyphenyl)-1-mercapto-2-aminoethane. Other substituted nitrostyrenes containing the 3,4-dimethoxy- and 3-methoxy-4-acetoxy groups also reacted with thiolacetic acid to give the corresponding addition products, but 3-acetoxy-4-methoxy-ω-nitrostyrene underwent an anomalous reaction with the formation of elemental

  将硫代乙酸添加到3,4-亚甲二氧基-ω-硝基苯乙烯中，得到1-（3'，4'-亚甲二氧基苯基）-1-乙酰硫基-2-硝基乙烷，用氢化铝锂还原生成1-（3'， 4′-亚甲基二氧苯基）-1-巯基-2-氨基乙烷。含有3,4-二甲氧基和3-甲氧基-4-乙酰氧基的其他取代的硝基苯乙烯也与硫代乙酸反应生成相应的加成产物，但3-乙酰氧基-4-甲氧基-ω-硝基苯乙烯与苯甲酸发生异常反应。元素硫的形成。1-苯基-2-硝基-1-丙烯加入硫代乙酸得到1-苯基-1-乙酰硫基-2-硝基丙烷，但是后者的化合物被氢化铝锂裂解成苄基硫醇和乙胺。
• Squaramide-catalysed enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes
  作者：Wen Yang、Da-Ming Du

  DOI：10.1039/c2ob26068a

  日期：——

  A highly enantio- and diastereoselective sulfa-Michael addition of thioacetic acid to α,β-disubstituted nitroalkenes catalysed by a chiral squaramide organocatalyst has been described. This organocatalytic reaction at an extremely low catalyst loading (0.2 mol%) furnished synthetically useful β-nitro sulfides in excellent yields with good diastereoselectivities and high enantioselectivities (up to 94 : 6 dr, 95% ee). In addition, the catalytic reaction can be performed on a 10 gram scale, and facile transformation into taurine derivative is also presented.

  在手性方酰胺有机催化剂的催化下，描述了硫代乙酸与δ±,δ²-二取代硝基烯的高对映和非对映选择性磺-迈克尔加成反应。这种有机催化反应的催化剂负载量极低（0.2 摩尔%），却能以极好的产率、良好的非对映选择性和较高的对映选择性（高达 94â:â6 dr，95% ee）合成出有用的δ-硝基硫化物。此外，该催化反应可以在 10 克的规模上进行，而且还能方便地转化为牛磺酸衍生物。