2-Nitro-1-acetylmercapto-1-phenyl-ethan | 29651-81-8

• 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: 2-Nitro-1-acetylmercapto-1-phenyl-ethan
• 英文别名: 1-thioacetyl-1-phenyl-2-nitroethane；1-acetythiol-1-phenyl-2-nitroethane；S-2-nitro-1-phenylethyl thiolacetate；1-Acetylthio-1-phenyl-2-nitroethane；S-(2-nitro-1-phenylethyl) ethanethioate
• CAS: 29651-81-8
• 化学式: C₁₀H₁₁NO₃S
• 分子量: 225.268
• InChiKey: YPTUXBSIFZOUKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-Nitro-1-acetylmercapto-1-phenyl-ethan 在 甲酸 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-nitro-1-phenylethane-1-sulfonic 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：

  β-硝基苯乙烯 、 硫代乙酸 反应 0.08h， 以98%的产率得到2-Nitro-1-acetylmercapto-1-phenyl-ethan
  参考文献：
  名称：

  在无溶剂和无催化剂条件下硫代乙酸 (AcSH) 与共轭烯烃的迈克尔加成反应

  摘要：

  在无溶剂和无催化剂的条件下，硫代乙酸 (AcSH) 与各种共轭烯烃的迈克尔加成反应已开发出一种新的方便的方法。这些反应在 5-60 分钟内进行，并以良好到高产率产生所需的产物。

  DOI：

  10.1080/10426500903496713

文献信息

• Organocatalytic enantioselective synthesis of β-amino sulfonic acid derivatives
  作者：Emmanuel Deau、Alexandra Le Foll、Clémence Fouache、Emilie Corrot、Laetitia Bailly、Vincent Levacher、Pierric Marchand、Florian Querniard、Laurent Bischoff、Jean-François Brière

  DOI：10.1039/d1cc03477d

  日期：——

  An unprecedented enantioselective conjugate addition reaction of sodium bisulfite to various nitrostyrenes occurred upon the influence of a bifunctional amino-thiourea organocatalyst; a strategy that opens a straightforward route to unprotected chiral taurine derivatives thanks to the reduction of the obtained β-nitroethanesulfonic acids into the corresponding amino derivatives.

  在双功能氨基硫脲有机催化剂的影响下，发生了前所未有的亚硫酸氢钠与各种硝基苯乙烯的对映选择性共轭加成反应；由于将获得的 β-硝基乙磺酸还原为相应的氨基衍生物，该策略为未保护的手性牛磺酸衍生物开辟了一条直接途径。
• 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。
• Organocatalytic enantioselective Michael addition of thioacetic acid to enones
  作者：Hao Li、Liansuo Zu、Jian Wang、Wei Wang

  DOI：10.1016/j.tetlet.2006.02.140

  日期：2006.5

  An enantioselective, organocatalytic Michael addition reaction of thioacetic acid with enones has been developed. The process, catalyzed by a chiral bifunctional amine thiourea, furnishes products in excellent yields with up to 63% ee.

  已开发出硫乙酸与烯酮的对映选择性有机催化迈克尔加成反应。通过手性双官能胺硫脲的催化，该工艺可提供高达63％ee的优异收率的产品。
• Synthese von 2-Thioaldosen �ber ?,?-unges�ttigte Nitrok�rper
  作者：P. Wirz、E. Hardegger

  DOI：10.1002/hlca.19710540731

  日期：1971.11.1

  Die basenkatalysierte Reaktion von Thiocarbonsäuren oder Benzylmercaptan mit dem aus D-Arabinose leicht zugänglichen α,β-ungesättigten Nitrokörper III verläuft kinetisch kontrolliert bevorzugt zu Verbindungen der Reihe V mit D-manno-Konfiguration. Am Beispiel des Benzylthioäthers Vb wurde ein präparativ gangbarer Weg zur Synthese von 2-Thio-D-mannose (XIV) und 2-Thio-D-glucose (XVIII) gewiesen.

  尼古丁二烯基苯甲酸酯类化合物或苯硫醇类化合物D-阿拉伯糖Leichtzugänglichenα，β-丁烯二酸酯NitrokörperIIIverläuftkinetisch kontrolliert bevorzugt zu VerbindungenKon - Refi 苯硫基醚（Beispiel desBenzylthioäthers）Vb wurde einpräparativgangbarer Weg zur合成了2-硫代-D-甘露糖（XIV）和2-硫代-D-葡萄糖（XVIII）的ewes。
• 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.