(R)-2-((4-chlorobenzyl)thio)-2-(2,4-dichlorophenyl)ethanamine | 1165796-83-7

• 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-((4-chlorobenzyl)thio)-2-(2,4-dichlorophenyl)ethanamine
• 英文别名: (2R)-2-[(4-chlorophenyl)methylsulfanyl]-2-(2,4-dichlorophenyl)ethanamine
• CAS: 1165796-83-7
• 化学式: C₁₅H₁₄Cl₃NS
• 分子量: 346.708
• InChiKey: DRGYZNPKVLOXMU-HNNXBMFYSA-N

物化性质

• 沸点：
  451.2±45.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 草酸醛 、 (R)-2-((4-chlorobenzyl)thio)-2-(2,4-dichlorophenyl)ethanamine 在 ammonium acetate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以71%的产率得到3-[2-(4-羟基-4-苯基-1-哌啶基)乙基]-2-(4-硝基苯基)硫杂偶氮千in-4-酮
  参考文献：
  名称：

  非对映选择性的α-亚磺酰ñ -叔-Butanesulfinyl亚氨酸酯

  摘要：

  手性的非对映选择性α-α亚磺酰-芳基/烷基ñ -叔-butanesulfinyl亚胺酸酯已经研制成功。合适的硫亲电试剂可用作亚磺酰化试剂，以拦截由亚氨酸酯去质子化生成的氮杂-烯醇酸酯，以高收率和高非对映异构控制性得到α-硫官能化的酰亚胺。该形成C–S键的方案可有效合成对映体富集的1,2-亚硫烷基胺衍生物，如舒康唑。

  DOI：

  10.1021/acs.joc.8b01403
• 作为产物：
  描述：

  4-氯苄溴 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

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。
• Diastereoselective α-Sulfenylation of <i>N</i>-<i>tert</i>-Butanesulfinyl Imidates
  作者：Sheng-Tong Niu、Hui Liu、Yan-Jun Xu、Chong-Dao Lu

  DOI：10.1021/acs.joc.8b01403

  日期：2018.9.7

  A diastereoselective α-sulfenylation of chiral α-aryl/alkyl N-tert-butanesulfinyl imidates has been developed. Suitable sulfur electrophiles can be used as sulfenylating reagents to intercept aza-enolates generated from imidate deprotonation, giving α-thiofunctionalized imidates in good yields with high diastereocontrol. This protocol for C–S bond formation can efficiently synthesize enantioenriched

  手性的非对映选择性α-α亚磺酰-芳基/烷基ñ -叔-butanesulfinyl亚胺酸酯已经研制成功。合适的硫亲电试剂可用作亚磺酰化试剂，以拦截由亚氨酸酯去质子化生成的氮杂-烯醇酸酯，以高收率和高非对映异构控制性得到α-硫官能化的酰亚胺。该形成C–S键的方案可有效合成对映体富集的1,2-亚硫烷基胺衍生物，如舒康唑。
• 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.