(R)-2-nitro-1-phenylethyl ethanethioate

• 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: (R)-2-nitro-1-phenylethyl ethanethioate
• 英文别名: S-[(1R)-2-nitro-1-phenylethyl] ethanethioate
• 化学式: C₁₀H₁₁NO₃S
• 分子量: 225.268
• InChiKey: YPTUXBSIFZOUKX-JTQLQIEISA-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

• 作为产物：
  描述：

  反式硝基苯乙烯 、 硫代乙酸 在 1-[(1R,2R)-2-(dimethylamino)cyclohexyl]-3-[(S)-[2,4,6-tri(propan-2-yl)phenyl]sulfinyl]urea 作用下， 以 环戊基甲醚 为溶剂， 反应 48.0h， 以73%的产率得到(R)-2-nitro-1-phenylethyl ethanethioate
  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

• 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 asymmetric conjugate addition of thioacetic acid to β-nitrostyrenes
  作者：Hao Li、Jian Wang、Liansuo Zu、Wei Wang

  DOI：10.1016/j.tetlet.2006.02.036

  日期：2006.4

  A method for organocatalytic, enantioselective Michael addition reactions of thioacetic acid with a range of trans-β-nitrostyrenes has been developed. The processes, promoted by the chiral amine thiourea organocatalyst, take place in high yields with up to 70% ee.

  已经开发出一种用于硫代乙酸与一系列反式-β-硝基苯乙烯的有机催化，对映选择性迈克尔加成反应的方法。由手性胺硫脲有机催化剂促进的过程以高收率和最高70％ee进行。
• 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。
• Enantioselective Sulfur-<i>Michael</i>Addition of Thioacetic Acid to Nitroalkenes Catalyzed by Bifunctional Amine-Thiourea Catalysts
  作者：Renchao Wang、Jiaxi Xu

  DOI：10.1002/hlca.201400125

  日期：2014.12

  An enantioselective Michael addition of thioacetic acid (AcSH) to nitroalkenes, catalyzed by a leucine‐derived bifunctional aminethiourea, was developed with high yields and moderate enantioselectivities. The thiourea‐ammonium salt formed in the reaction is identified as the active catalyst, and the multiple H‐bonding system is responsible for the stereocontrol. The resulting thioester products are

  开发了由亮氨酸衍生的双官能胺硫脲催化的硫代乙酸（AcSH）对硝基烯烃的对映选择性迈克尔加成反应，具有高收率和中等对映选择性。反应中形成的硫脲-铵盐被鉴定为活性催化剂，多重氢键系统负责立体控制。所得的硫酯产物是用于合成对映体富集的含S化合物的有用中间体。