Carbonic acid (3,5-dimethoxy-phenyl)-(2-phenyl-[1,3]dithian-2-yl)-methyl ester 2-nitro-phenyl ester | 202996-37-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: Carbonic acid (3,5-dimethoxy-phenyl)-(2-phenyl-[1,3]dithian-2-yl)-methyl ester 2-nitro-phenyl ester
• 英文别名: [(3,5-dimethoxyphenyl)-(2-phenyl-1,3-dithian-2-yl)methyl] (2-nitrophenyl) carbonate
• CAS: 202996-37-0
• 化学式: C₂₆H₂₅NO₇S₂
• 分子量: 527.619
• InChiKey: CWJGKKIPRFASGG-UHFFFAOYSA-N

物化性质

• 沸点：
  695.8±55.0 °C(predicted)
• 密度：
  1.334±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  97.13
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2,6-二甲氧基苯酚 、 Carbonic acid (3,5-dimethoxy-phenyl)-(2-phenyl-[1,3]dithian-2-yl)-methyl ester 2-nitro-phenyl ester 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以99%的产率得到(2,6-dimethoxyphenyl) [(3,5-dimethoxyphenyl)-(2-phenyl-1,3-dithian-2-yl)methyl] carbonate
  参考文献：
  名称：

  Design, Synthesis, and Photochemical Properties of a Photoreleasable Ubiquinol-2:  A Novel Compound for Studying Rapid Electron-Transfer Kinetics in Ubiquinol-Oxidizing Enzymes

  摘要：

  The design and multistep convergent synthesis of the novel photoactive ubiquinol-benzoin adduct 1a,b has been accomplished. Optical spectra of the steady-state photolysis reactions showed a smooth conversion from 1a,b to 5,7-dimethoxy-2-phenylbenzofuran (13) and ubiquinol-2 with an isobestic point at 258 nm. HPLC analysis of the photoproducts was also consistent with the clean formation of the desired ubiquinol-2 (3) and the expected 5,7-dimethoxy-2-phenylbenzofuran (2). Transient photolysis at 355 nm was consistent with a rapid photolysis rate that exceeded the instrument response time (>10(6) s(-1)). Accordingly, the study of rapid electron-transfer events in ubiquinol oxidizing enzymes is now feasible. Furthermore, the synthetic methods developed herein will be of general application for the facile synthesis of a variety of photoreleasable substrates for studying rapid kinetic events in enzymatic reactions.

  DOI：

  10.1021/ja971079j
• 作为产物：
  描述：

  2-苯基-1,3-二噻烷 在 吡啶 、 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 Carbonic acid (3,5-dimethoxy-phenyl)-(2-phenyl-[1,3]dithian-2-yl)-methyl ester 2-nitro-phenyl ester
  参考文献：
  名称：

  Design, Synthesis, and Photochemical Properties of a Photoreleasable Ubiquinol-2:  A Novel Compound for Studying Rapid Electron-Transfer Kinetics in Ubiquinol-Oxidizing Enzymes

  摘要：

  The design and multistep convergent synthesis of the novel photoactive ubiquinol-benzoin adduct 1a,b has been accomplished. Optical spectra of the steady-state photolysis reactions showed a smooth conversion from 1a,b to 5,7-dimethoxy-2-phenylbenzofuran (13) and ubiquinol-2 with an isobestic point at 258 nm. HPLC analysis of the photoproducts was also consistent with the clean formation of the desired ubiquinol-2 (3) and the expected 5,7-dimethoxy-2-phenylbenzofuran (2). Transient photolysis at 355 nm was consistent with a rapid photolysis rate that exceeded the instrument response time (>10(6) s(-1)). Accordingly, the study of rapid electron-transfer events in ubiquinol oxidizing enzymes is now feasible. Furthermore, the synthetic methods developed herein will be of general application for the facile synthesis of a variety of photoreleasable substrates for studying rapid kinetic events in enzymatic reactions.

  DOI：

  10.1021/ja971079j