1-tert-butyl-1H-tetrazol-5-yl fluoromethyl sulfone | 1236300-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-tert-butyl-1H-tetrazol-5-yl fluoromethyl sulfone
• 英文别名: 1-(Tert-butyl)-5-((fluoromethyl)sulfonyl)-1H-tetrazole；1-tert-butyl-5-(fluoromethylsulfonyl)tetrazole
• CAS: 1236300-44-9
• 化学式: C₆H₁₁FN₄O₂S
• 分子量: 222.243
• InChiKey: CAWKMMBKHWNUCY-UHFFFAOYSA-N

物化性质

• 沸点：
  357.7±44.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  86.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-tert-butyl-1H-tetrazol-5-yl fluoromethyl sulfone 在 N-碘代丁二酰亚胺 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以75%的产率得到1-Tert-butyl-5-[fluoro(iodo)methyl]sulfonyltetrazole
  参考文献：
  名称：

  Copper-Mediated Fluoroalkylation of Aryl Iodides Enables Facile Access to Diverse Fluorinated Compounds: The Important Role of the (2-Pyridyl)sulfonyl Group

  摘要：

  The (2-pyridyl)sulfonyl group was found to be a multifunctional group in the preparation of structurally diverse fluorinated products. It not only facilitates the copper-mediated (or catalyzed) cross-coupling reaction between a-fluoro sulfone 4a and aryl iodides, but also enables further transformations of the coupling products 2.

  DOI：

  10.1021/ol3029737
• 作为产物：
  描述：

  1-叔丁基-1H-四唑-5-基甲基砜 在 六甲基磷酰三胺 、 正丁基锂 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以8%的产率得到1-tert-butyl-1H-tetrazol-5-yl fluoromethyl sulfone
  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

文献信息

• Enantioselective synthesis of Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums
  作者：Yun Zhang、Yibin Xue、Gang Li、Haosen Yuan、Tuoping Luo

  DOI：10.1039/c6sc00932h

  日期：——

  and novel strategy for the enantioselective syntheses of various iboga alkaloids has been developed. The salient features include a gold-catalyzed oxidation of a terminal alkyne followed by cyclization, a Stevens rearrangement and a tandem sequence that combines the gold-catalyzed oxidation, cyclization and [1,2]-shift. The catharanthine analogs provided by our approach were further converted to the

  已经开发出一种有效且新颖的策略，用于各种伊博加生物碱的对映体选择性合成。其显着特征包括末端炔的金催化氧化，随后环化，史蒂文斯重排和串联序列，该序列结合了金催化的氧化，环化和[1,2]移位。我们的方法提供的catharanthine类似物进一步转化为长春花生物碱长春碱及其类似物，这证实了细胞毒性对长春碱C20'取代基的显着敏感性。
• Copper-Mediated Fluoroalkylation of Aryl Iodides Enables Facile Access to Diverse Fluorinated Compounds: The Important Role of the (2-Pyridyl)sulfonyl Group
  作者：Yanchuan Zhao、Bing Gao、Chuanfa Ni、Jinbo Hu

  DOI：10.1021/ol3029737

  日期：2012.12.7

  The (2-pyridyl)sulfonyl group was found to be a multifunctional group in the preparation of structurally diverse fluorinated products. It not only facilitates the copper-mediated (or catalyzed) cross-coupling reaction between a-fluoro sulfone 4a and aryl iodides, but also enables further transformations of the coupling products 2.
• 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
  作者：Lingui Zhu、Chuanfa Ni、Yanchuan Zhao、Jinbo Hu

  DOI：10.1016/j.tet.2010.04.113

  日期：2010.7

  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.