methyl 4,5,6,7-tetrafluoro-3-phenyl-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide | 1049837-84-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 4,5,6,7-tetrafluoro-3-phenyl-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide
• 英文别名: methyl 4,5,6,7-tetrafluoro-1,1-dioxo-3-phenyl-2H-1,2-benzothiazole-3-carboxylate
• CAS: 1049837-84-4
• 化学式: C₁₅H₉F₄NO₄S
• 分子量: 375.3
• InChiKey: LDYPUVDFBZTXQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 4,5,6,7-tetrafluoro-3-phenyl-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide 、 1-碘代丙烷 在 苄基三乙基氯化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 以87%的产率得到methyl (R)-4,5,6,7-tetrafluoro-2-propyl-3-phenyl-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide
  参考文献：
  名称：

  Memory of Chirality Approach to the Enantiodivergent Synthesis of Chiral Benzo[d]sultams

  摘要：

  The "memory of chirality" stereodivergent synthesis of polyfluorobenzo[d]sultams has been developed. The interest of this protocol resides in the possibility of using the chirality of a starting sulfonamide single enantiomer to synthesize the target sultams in both absolute configurations, by using different base systems, under homogeneous conditions.

  DOI：

  10.1021/ol401557v
• 作为产物：
  描述：

  2,3,4,5,6-五氟苯磺酰氯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 19.0h， 生成 methyl 4,5,6,7-tetrafluoro-3-phenyl-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide
  参考文献：
  名称：

  Memory of Chirality Approach to the Enantiodivergent Synthesis of Chiral Benzo[d]sultams

  摘要：

  The "memory of chirality" stereodivergent synthesis of polyfluorobenzo[d]sultams has been developed. The interest of this protocol resides in the possibility of using the chirality of a starting sulfonamide single enantiomer to synthesize the target sultams in both absolute configurations, by using different base systems, under homogeneous conditions.

  DOI：

  10.1021/ol401557v

文献信息

• Complementary Heterogeneous/Homogeneous Protocols for the Synthesis of Densely Functionalized Benzo[<i>d</i>]sultams: C−C Bond Formation by Intramolecular Nucleophilic Aromatic Fluorine Displacement
  作者：Michele Penso、Domenico Albanese、Dario Landini、Vittoria Lupi、Aaron Tagliabue

  DOI：10.1021/jo800930g

  日期：2008.9.1

  from the corresponding open chain (pentafluorobenzene)sulfonamides 4 by complementary solid-liquid phase transfer catalysis (SL-PTC) and homogeneous protocols. The cyclization step proceeds through the intramolecular nucleophilic displacement of an aromatic fluorine atom.

  通过互补的固-液相转移催化（SL-PTC）和均相方案，由相应的开链（五氟苯）磺酰胺4合成了含有α-氨基酸单元的多官能化苯并[d] sultams 7和8。环化步骤通过芳族氟原子的分子内亲核取代进行。
• Memory of Chirality Approach to the Enantiodivergent Synthesis of Chiral Benzo[<i>d</i>]sultams
  作者：Francesca Foschi、Aaron Tagliabue、Voichita Mihali、Tullio Pilati、Ilir Pecnikaj、Michele Penso

  DOI：10.1021/ol401557v

  日期：2013.7.19

  The "memory of chirality" stereodivergent synthesis of polyfluorobenzo[d]sultams has been developed. The interest of this protocol resides in the possibility of using the chirality of a starting sulfonamide single enantiomer to synthesize the target sultams in both absolute configurations, by using different base systems, under homogeneous conditions.