3-cyclohexyl-4-trifluoromethanesulfonyloxy-benzoic acid methyl ester | 924283-06-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-cyclohexyl-4-trifluoromethanesulfonyloxy-benzoic acid methyl ester
• 英文别名: Methyl 3-cyclohexyl-4-(trifluoromethanesulfonyloxy)benzoate；methyl 3-cyclohexyl-4-(trifluoromethylsulfonyloxy)benzoate
• CAS: 924283-06-7
• 化学式: C₁₅H₁₇F₃O₅S
• 分子量: 366.358
• InChiKey: XMMLEGHAAPECSC-UHFFFAOYSA-N

物化性质

• 沸点：
  415.9±45.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-cyclohexyl-4-trifluoromethanesulfonyloxy-benzoic acid methyl ester 在 1,1'-双(二苯基膦)二茂铁 、 草酰氯 、 2-碘联苯 、 potassium acetate 、 palladium diacetate 、 potassium carbonate 、 N,N-二甲基甲酰胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 0.25h， 生成 methyl 2'-methoxy-3'-oxospiro[cyclohexane-1,1'-isoindoline]-6'-carboxylate
  参考文献：
  名称：

  Iodoarene-Catalyzed Stereospecific Intramolecular sp³ C–H Amination: Reaction Development and Mechanistic Insights

  摘要：

  A new strategy is reported for intramolecular Sp(3) C-H amination :under mild reaction conditions using iodoarene as catalyst and m-CPBA as oxidant. This C-H functionalization involving iodine(III) reagents generated in situ occurs readily at sterically hindered tertiary C-H bonds. DFT (M06-2X) calculations show that the preferred pathway involves an iodonium cation intermediate and proceeds via an energetically concerted transition state, through hydride transfer followed by the spontaneous C-N bond formation. ThiS leads to the experimentally observed amination at a chiral center without loss of stereo chemical information.

  DOI：

  10.1021/jacs.5b03488
• 作为产物：
  描述：

  4-bromo-2-cyclohexylphenol 在 吡啶 、 1,1'-双(二苯基膦)二茂铁 、 potassium acetate 、 palladium diacetate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 29.0h， 生成 3-cyclohexyl-4-trifluoromethanesulfonyloxy-benzoic acid methyl ester
  参考文献：
  名称：

  Iodoarene-Catalyzed Stereospecific Intramolecular sp³ C–H Amination: Reaction Development and Mechanistic Insights

  摘要：

  A new strategy is reported for intramolecular Sp(3) C-H amination :under mild reaction conditions using iodoarene as catalyst and m-CPBA as oxidant. This C-H functionalization involving iodine(III) reagents generated in situ occurs readily at sterically hindered tertiary C-H bonds. DFT (M06-2X) calculations show that the preferred pathway involves an iodonium cation intermediate and proceeds via an energetically concerted transition state, through hydride transfer followed by the spontaneous C-N bond formation. ThiS leads to the experimentally observed amination at a chiral center without loss of stereo chemical information.

  DOI：

  10.1021/jacs.5b03488

文献信息

• 6-Membered aryl and heteroaryl derivatives for treating viruses
  申请人：Botyanszki Janos

  公开号：US20070032488A1

  公开（公告）日：2007-02-08

  Disclosed are compounds, compositions and methods for treating Flaviviridae family virus infections.

  公开了用于治疗黄病毒科病毒感染的化合物、组合物和方法。
• [EN] 6-MEMBERED ARYL AND HETEROARYL DERIVATIVES FOR TREATING VIRUSES<br/>[FR] DERIVES D'ARYLE ET HETEROARYLE A 6 MEMBRES POUR LE TRAITEMENT DE VIRUS
  申请人：GENELABS TECH INC

  公开号：WO2007019397A2

  公开（公告）日：2007-02-15

  [EN] Disclosed are compounds, compositions and methods for treatingFlaviviridae family virus infections.
  [FR] L'invention concerne des composés, des compositions et des méthodes de traitement d'infections virales de la famille Flaviviridae.
• Iodoarene-Catalyzed Stereospecific Intramolecular sp³ C–H Amination: Reaction Development and Mechanistic Insights
  作者：Chendan Zhu、Yong Liang、Xin Hong、Heqing Sun、Wei-Yin Sun、K. N. Houk、Zhuangzhi Shi

  DOI：10.1021/jacs.5b03488

  日期：2015.6.24

  A new strategy is reported for intramolecular Sp(3) C-H amination :under mild reaction conditions using iodoarene as catalyst and m-CPBA as oxidant. This C-H functionalization involving iodine(III) reagents generated in situ occurs readily at sterically hindered tertiary C-H bonds. DFT (M06-2X) calculations show that the preferred pathway involves an iodonium cation intermediate and proceeds via an energetically concerted transition state, through hydride transfer followed by the spontaneous C-N bond formation. ThiS leads to the experimentally observed amination at a chiral center without loss of stereo chemical information.