3-benzoyl-1-[2-(1,3-benzothiazole-2-sulfonyl)-2-fluoroethyl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione | 1449219-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 3-benzoyl-1-[2-(1,3-benzothiazole-2-sulfonyl)-2-fluoroethyl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• 英文别名: 1-[2-(1,3-Benzothiazol-2-ylsulfonyl)-2-fluoroethyl]-3-benzoyl-5-methylpyrimidine-2,4-dione；1-[2-(1,3-benzothiazol-2-ylsulfonyl)-2-fluoroethyl]-3-benzoyl-5-methylpyrimidine-2,4-dione
• CAS: 1449219-35-5
• 化学式: C₂₁H₁₆FN₃O₅S₂
• 分子量: 473.506
• InChiKey: AKIDXZGRTDSGIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-benzoyl-1-[2-(1,3-benzothiazole-2-sulfonyl)-2-fluoroethyl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione 在 sodium hexamethyldisilazane 、 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 34.0h， 生成 1-[2-Fluoro-4-hydroxy-3-(hydroxymethyl)but-2-enyl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Aza-Michael Access to Fluoroalkylidene Analogues of Biomolecules

  摘要：

  The synthesis of fluoroaminosulfones derived from piperidine and nucleic bases followed by the study of their chemical behavior in the modified Julia reaction are described. The resulting aminosulfones open a straightforward access to a series of new fluorinated biomolecules including a potent DPP-II inhibitor and acyclonucleoside analogues as potential enzyme inhibitors.

  DOI：

  10.1021/jo401356j
• 作为产物：
  描述：

  2-[(1-fluorovinyl)sulfonyl]-1,3-benzothiazole 、 N-3-benzoylthymine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以95%的产率得到3-benzoyl-1-[2-(1,3-benzothiazole-2-sulfonyl)-2-fluoroethyl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
  参考文献：
  名称：

  Aza-Michael Access to Fluoroalkylidene Analogues of Biomolecules

  摘要：

  The synthesis of fluoroaminosulfones derived from piperidine and nucleic bases followed by the study of their chemical behavior in the modified Julia reaction are described. The resulting aminosulfones open a straightforward access to a series of new fluorinated biomolecules including a potent DPP-II inhibitor and acyclonucleoside analogues as potential enzyme inhibitors.

  DOI：

  10.1021/jo401356j

文献信息

• Synthesis of Fluorine-Containing 3,3-Disubstituted Oxetanes and Alkylidene Oxetanes
  作者：Romain Laporte、Anais Prunier、Emmanuel Pfund、Vincent Roy、Luigi A. Agrofoglio、Thierry Lequeux

  DOI：10.1002/ejoc.201500172

  日期：2015.5

  contain a nucleic base, an ester or aryl sulfone function, and a pyrrolidine ring. Benzothiazolyl-sulfone-mediated aza-Michael addition reaction of nitrogen nucleophiles enables access to 3,3-disubstituted oxetanes.

  通过 Julia-Kocienski 反应从 3-氧杂环丁酮、3-氮杂环丁酮和氟砜实现了对氟亚烷基-氧杂环丁烷和 -氮杂环丁烷的访问。这种方法允许制备包含核碱基、酯或芳基砜功能和吡咯烷环的氟化四元环的新前体。苯并噻唑基砜介导的氮亲核试剂的氮杂-迈克尔加成反应能够获得 3,3-二取代氧杂环丁烷。
• Aza-Michael Access to Fluoroalkylidene Analogues of Biomolecules
  作者：Anaïs Prunier、Charlène Calata、Julien Legros、Jacques Maddaluno、Emmanuel Pfund、Thierry Lequeux

  DOI：10.1021/jo401356j

  日期：2013.8.16

  The synthesis of fluoroaminosulfones derived from piperidine and nucleic bases followed by the study of their chemical behavior in the modified Julia reaction are described. The resulting aminosulfones open a straightforward access to a series of new fluorinated biomolecules including a potent DPP-II inhibitor and acyclonucleoside analogues as potential enzyme inhibitors.