N-[2-(1,3-benzothiazol-2-ylsulfonyl)-2-fluoroethyl]-cyclohexanamine | 1200123-18-7

• 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: N-[2-(1,3-benzothiazol-2-ylsulfonyl)-2-fluoroethyl]-cyclohexanamine
• 英文别名: N-[2-(1,3-benzothiazol-2-ylsulfonyl)-2-fluoroethyl]cyclohexanamine
• CAS: 1200123-18-7
• 化学式: C₁₅H₁₉FN₂O₂S₂
• 分子量: 342.458
• InChiKey: MXVHGUWCKGQMSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[2-(1,3-benzothiazol-2-ylsulfonyl)-2-fluoroethyl]-cyclohexanamine 、 4-叔丁基环己酮 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 以78%的产率得到N-[2-(4-tert-butylcyclohexylidene)-2-fluoroethyl]cyclohexylamine
  参考文献：
  名称：

  Convergent synthesis of functionalized fluoroallylamines by the Julia–Kocienski reaction

  摘要：

  The synthesis of beta-fluoroallylamines is reported from aminofluorobenzothiazolylsulfones. These open a new route for a short synthesis of vinylic fluoride containing highly functionalized amino residues. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.061
• 作为产物：
  描述：

  2-[(1-fluorovinyl)sulfonyl]-1,3-benzothiazole 、 环己胺 在 水 、 氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以82%的产率得到N-[2-(1,3-benzothiazol-2-ylsulfonyl)-2-fluoroethyl]-cyclohexanamine
  参考文献：
  名称：

  Toward the Synthesis of Benzothiazolyl Fluoroaminosulfones

  摘要：

  Due to the importance of allylamines in organic synthesis, the synthesis of reagents as potent precursors of aminofluoroolefins is reported from functionalized benzothiazolylsulfones. The key intermediate, a fluorovinyl sulfone, was prepared and functionalized by addition of aliphatic, aromatic amines and amino acid alkyl esters through an aza-Michael addition reaction.

  DOI：

  10.1021/jo901540c

文献信息

• Convergent synthesis of functionalized fluoroallylamines by the Julia–Kocienski reaction
  作者：Charlène Calata、Emmanuel Pfund、Thierry Lequeux

  DOI：10.1016/j.tet.2010.12.061

  日期：2011.2

  The synthesis of beta-fluoroallylamines is reported from aminofluorobenzothiazolylsulfones. These open a new route for a short synthesis of vinylic fluoride containing highly functionalized amino residues. (C) 2010 Elsevier Ltd. All rights reserved.
• Toward the Synthesis of Benzothiazolyl Fluoroaminosulfones
  作者：Charlène Calata、Emmanuel Pfund、Thierry Lequeux

  DOI：10.1021/jo901540c

  日期：2009.12.18

  Due to the importance of allylamines in organic synthesis, the synthesis of reagents as potent precursors of aminofluoroolefins is reported from functionalized benzothiazolylsulfones. The key intermediate, a fluorovinyl sulfone, was prepared and functionalized by addition of aliphatic, aromatic amines and amino acid alkyl esters through an aza-Michael addition reaction.