ethyl 2-(1-tert-butyl-1H-tetrazol-5-ylsulfonyl)-2-fluoroacetate | 1236300-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-(1-tert-butyl-1H-tetrazol-5-ylsulfonyl)-2-fluoroacetate
• 英文别名: Ethyl 2-(1-tert-butyltetrazol-5-yl)sulfonyl-2-fluoroacetate；ethyl 2-(1-tert-butyltetrazol-5-yl)sulfonyl-2-fluoroacetate
• CAS: 1236300-71-2
• 化学式: C₉H₁₅FN₄O₄S
• 分子量: 294.307
• InChiKey: GJMPMXWHOOMDOL-UHFFFAOYSA-N

物化性质

• 沸点：
  426.1±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-(1-tert-butyl-1H-tetrazol-5-ylsulfonyl)-2-fluoroacetate 、 2-萘甲醛 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl (E)-2-fluoro-3-(2-naphthyl)-2-propenoate 、 (Z)-ethyl 2-fluoro-3-(naphthalen-2-yl)acrylate
  参考文献：
  名称：

  1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F): a versatile fluoromethylidene synthon and its use in the synthesis of monofluorinated alkenes via Julia–Kocienski olefination

  摘要：

  1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F) has been developed as a new and efficient fluoromethylidene synthon for the synthesis of both terminal and internal monofluoroalkenes via Julia-Kocienski olefination reaction. The base-mediated reaction between TBTSO2CH2F and carbonyl compounds (aldehydes and ketones) provided terminal monofluoroalkenes in good yields with moderate E/Z selectivity. The dominance of E- or Z-fluoroalkenes could be controlled by selection of proper reaction solvent and temperature. TBTSO2CH2F reagent was also found to be readily a-alkylated, acylated, and phenylsulfonylated to give corresponding alpha-functionalized fluorosulfones, which could be used in the synthesis of alkyl-, acyl-, and phenylsulfonyl-substituted internal monofluoroalkenes via Julia-Kocienski olefination reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.113
• 作为产物：
  描述：

  1-tert-butyl-1H-tetrazol-5-yl fluoromethyl sulfone 、 碳酸二乙酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到ethyl 2-(1-tert-butyl-1H-tetrazol-5-ylsulfonyl)-2-fluoroacetate
  参考文献：
  名称：

  1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F): a versatile fluoromethylidene synthon and its use in the synthesis of monofluorinated alkenes via Julia–Kocienski olefination

  摘要：

  1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F) has been developed as a new and efficient fluoromethylidene synthon for the synthesis of both terminal and internal monofluoroalkenes via Julia-Kocienski olefination reaction. The base-mediated reaction between TBTSO2CH2F and carbonyl compounds (aldehydes and ketones) provided terminal monofluoroalkenes in good yields with moderate E/Z selectivity. The dominance of E- or Z-fluoroalkenes could be controlled by selection of proper reaction solvent and temperature. TBTSO2CH2F reagent was also found to be readily a-alkylated, acylated, and phenylsulfonylated to give corresponding alpha-functionalized fluorosulfones, which could be used in the synthesis of alkyl-, acyl-, and phenylsulfonyl-substituted internal monofluoroalkenes via Julia-Kocienski olefination reactions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.113