(S)-(2,3,3a,4-Tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]thiazin-7-yl)-carbamic acid benzyl ester | 909020-10-6

• 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: (S)-(2,3,3a,4-Tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]thiazin-7-yl)-carbamic acid benzyl ester
• CAS: 909020-10-6
• 化学式: C₁₉H₂₀N₂O₂S
• 分子量: 340.446
• InChiKey: CJMPCQQUAPEDFV-INIZCTEOSA-N

物化性质

• 沸点：
  484.3±45.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  41.57
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-(2,3,3a,4-Tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]thiazin-7-yl)-carbamic acid benzyl ester 在 正丁基锂 、 sodium azide 、 水 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 ((S)-2-Oxo-3-(S)-2,3,3a,4-tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]thiazin-7-yl-oxazolidin-5-ylmethyl)-thiocarbamic acid O-methyl ester
  参考文献：
  名称：

  Synthesis of novel tricyclic oxazolidinones by a tandem SN2 and SNAr reaction: SAR studies on conformationally constrained analogues of Linezolid

  摘要：

  A series of conformationally constrained analogues of Linezolid were synthesised by employing a tandem SN2 and SNAr reaction as the key step and tested for antibacterial activity. While the hexahydroazolo-quinoxaline compounds were inactive, the tetrahydroazolo-benzothiazine compounds exhibited interesting antibacterial activity. The introduction of fluorine in the aromatic ring further made the compounds more potent in acetamide compounds resulting in an interesting analogue 32. However, the introduction of fluorine (analogue 34) on the already potent non-fluorine thiocarbamate 21 did not have any influence on the activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.071
• 作为产物：
  描述：

  L-脯氨醇 在 盐酸 、 四溴化碳 、 铁粉 、 sodium hydride 、 sodium carbonate 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 19.75h， 生成 (S)-(2,3,3a,4-Tetrahydro-1H-benzo[b]pyrrolo[1,2-d][1,4]thiazin-7-yl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of novel tricyclic oxazolidinones by a tandem SN2 and SNAr reaction: SAR studies on conformationally constrained analogues of Linezolid

  摘要：

  A series of conformationally constrained analogues of Linezolid were synthesised by employing a tandem SN2 and SNAr reaction as the key step and tested for antibacterial activity. While the hexahydroazolo-quinoxaline compounds were inactive, the tetrahydroazolo-benzothiazine compounds exhibited interesting antibacterial activity. The introduction of fluorine in the aromatic ring further made the compounds more potent in acetamide compounds resulting in an interesting analogue 32. However, the introduction of fluorine (analogue 34) on the already potent non-fluorine thiocarbamate 21 did not have any influence on the activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.071