(R)-1-Phenylethanesulfonamide | 150850-07-0

• 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)-1-Phenylethanesulfonamide
• 英文别名: (1R)-1-phenylethane-1-sulfonamide；(1R)-1-phenylethanesulfonamide
• CAS: 150850-07-0
• 化学式: C₈H₁₁NO₂S
• 分子量: 185.247
• InChiKey: SPSQEKCXVRMSBW-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲磺酰胺 在 盐酸 、 四氯化钛 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 1,1,2-三氯乙烷 为溶剂， 反应 27.0h， 生成 (R)-1-Phenylethanesulfonamide
  参考文献：
  名称：

  Asymmetric synthesis of .alpha.-functionalized primary sulfonamides

  摘要：

  Alpha-Functionalized primary sulfonamides 8 are prepared in good to excellent yields by treatment of the dianions of N-sulfonylcamphorimines 1-3 with electrophiles and hydrolysis of the resulting imines 5-7. Alkylation of the anions of N-sulfonyl-10-camphorsulfonamide imines 2 and 3 with primary and secondary alkyl iodides and with ethylene oxide, following removal of the chiral auxiliary with aqueous acid, gave primary sulfonamides with ee's in the range of 66-95%.

  DOI：

  10.1021/jo00070a026

文献信息

• [EN] FUSED-RING COMPOUNDS, PHARMACEUTICAL COMPOSITION AND USES THEREOF<br/>[FR] COMPOSÉS À CYCLES CONDENSÉS, COMPOSITION PHARMACEUTIQUE ET UTILISATIONS ASSOCIÉES
  申请人：SHANGHAI DE NOVO PHARMATECH CO LTD

  公开号：WO2016131380A1

  公开（公告）日：2016-08-25

  This disclosure is related to a fused-ring compound of formula (I) and/or a pharmaceutically acceptable salt thereof, a pharmaceutical composition comprising the fused ring compound of formula (I) and/or a pharmaceutically acceptable salt thereof, preparation methods thereof, and use thereof in modulating activity of indoleamine 2, 3-dioxygenase (IDO) and/or tryptophan 2, 3-dioxygenase (TDO). This disclosure further provides methods of treating IDO and/or TDO-associated diseases, including cancer, viral infection and autoimmune diseases.

  这份披露涉及到式(I)的融合环化合物和/或其药学上可接受的盐，包括式(I)的融合环化合物和/或其药学上可接受的盐的药物组合物，其制备方法，以及在调节吲哚胺2,3-二氧化酶(IDO)和/或色氨酸2,3-二氧化酶(TDO)活性中的应用。这份披露还提供了治疗IDO和/或TDO相关疾病的方法，包括癌症、病毒感染和自身免疫疾病。
• Convenient Route to Secondary Sulfinates: Application to the Stereospecific Synthesis of α-<i>C</i>-Chiral Sulfonamides
  作者：Michael G. Johnson、Michael W. Gribble、Jonathan B. Houze、Nick A. Paras

  DOI：10.1021/ol503208z

  日期：2014.12.5

  A convenient synthesis of a-chiral sulfinates from readily available precursors has been accomplished via the corresponding heterocyclic thioethers and sulfones. Treatment of the sulfinates with hydroxylamine sulfonate in aqueous solution provides alpha-C-chiral primary sulfonamides in good yield (14 examples) with retention of stereochemical purity.