(1S,2R)-2-nitro-1,2-diphenylethyl ethanethioate | 1397266-47-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,2R)-2-nitro-1,2-diphenylethyl ethanethioate
• 英文别名: S-[(1S,2R)-2-nitro-1,2-diphenylethyl] ethanethioate
• CAS: 1397266-47-5
• 化学式: C₁₆H₁₅NO₃S
• 分子量: 301.366
• InChiKey: WGHDHXMFKABZSF-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-nitro-1,2-diphenylethyl ethanethioate 在 甲酸 、 palladium 10% on activated carbon 、 氢气 、 双氧水 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 (+/-)-erythro-2-Amino-1,2-diphenylethanesulfonic acid
  参考文献：
  名称：

  Facile synthesis of various substituted taurines, especially syn- and anti-1,2-disubstituted taurines, from nitroolefins

  摘要：

  Taurine and substituted taurines present a group of important structural elements in many natural products. Various substituted taurines, including 1- and 2-substituted, 1,1-, syn-1,2-, and anti-1,2-disubstituted taurines, were synthesized from the corresponding nitroolefins via Michael addition with thioacetic acid, oxidation with peroxyformic acid, and the catalytic hydrogenation under the catalysis of palladium on carbon or platinum dioxide. It is a general, versatile, and salt-free method for the preparation of substituted taurines, especially for syn- and anti-1,2-disubstituted taurines and some taurines with more bulky substituents. The stereostructures of both syn- and anti-1,2-disubstituted taurines were deduced from the nitroalkyl thioacetates in the Michael addition, which were identified via the Karplus equation analysis and computational analysis, and finally confirmed by the XRD single crystal analysis. The diastereoselectivity in the Michael addition was rationalized with the Cram rule. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.031
• 作为产物：
  描述：

  硫代乙酸 、 (1-硝基-2-苯乙烯基)苯 在 三正丁胺 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以1%的产率得到S-2-nitro-1,2-diphenylethyl thiolacetate
  参考文献：
  名称：

  Facile synthesis of various substituted taurines, especially syn- and anti-1,2-disubstituted taurines, from nitroolefins

  摘要：

  Taurine and substituted taurines present a group of important structural elements in many natural products. Various substituted taurines, including 1- and 2-substituted, 1,1-, syn-1,2-, and anti-1,2-disubstituted taurines, were synthesized from the corresponding nitroolefins via Michael addition with thioacetic acid, oxidation with peroxyformic acid, and the catalytic hydrogenation under the catalysis of palladium on carbon or platinum dioxide. It is a general, versatile, and salt-free method for the preparation of substituted taurines, especially for syn- and anti-1,2-disubstituted taurines and some taurines with more bulky substituents. The stereostructures of both syn- and anti-1,2-disubstituted taurines were deduced from the nitroalkyl thioacetates in the Michael addition, which were identified via the Karplus equation analysis and computational analysis, and finally confirmed by the XRD single crystal analysis. The diastereoselectivity in the Michael addition was rationalized with the Cram rule. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.031

文献信息

• 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。