(+/-)-10-ethyl-5-oxo-5,10-dihydro-5λ⁴-phenothiazine-3-carbaldehyde | 459454-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: (+/-)-10-ethyl-5-oxo-5,10-dihydro-5λ⁴-phenothiazine-3-carbaldehyde
• 英文别名: 10-Ethyl-5-oxophenothiazine-3-carbaldehyde；10-ethyl-5-oxophenothiazine-3-carbaldehyde
• CAS: 459454-56-9
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: PJSNPXVKDBMSMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  67.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-10-ethyl-5-oxo-5,10-dihydro-5λ⁴-phenothiazine-3-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以89%的产率得到(+/-)-(10-ethyl-5-oxo-5,10-dihydro-5λ⁴-phenothiazin-3-yl)methanol
  参考文献：
  名称：

  Synthesis of optically active 3-substituted-10-alkyl-10H-phenothiazine-5-oxides by enantioselective biotransformations

  摘要：

  A series of racemic 10-alkyl-3-formyl-10H-phenothiazine-5-oxides (+/-)-2a-h were subjected to biotransformation with baker's yeast resulting in optically active aldehydes (+)-2a-h and alcohols (-)-3a-h in moderate enantiomeric excess. The racemic 10-alkyl-3-hydroxymethyl-10H-phenothiazine-5-oxides (+/-)-3a-h and 3-acetoxymethyl-10-alkyl-10H-phenothiazine-5-oxides (+/-)-4a-h obtained from the racemic aldehydes ()-2a-h were also tested in enantioselective lipase-catalyzed acetylations and alcoholysis reactions. The highest enantiomeric purities were achieved by a Novozyme 435-catalyzed acetylation-ethanolysis sequence, leading to optically active alcohols (-)-3a h in 83-92% e.e. A novel NMR method using enantiopure dibenzoyl tartaric acid as chiral additive was developed for determination of the enantiomeric composition of the optically active products. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00077-0
• 作为产物：
  描述：

  10-ethyl-10H-phenothiazine-3-carbaldehyde 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到(+/-)-10-ethyl-5-oxo-5,10-dihydro-5λ⁴-phenothiazine-3-carbaldehyde
  参考文献：
  名称：

  Synthesis of optically active 3-substituted-10-alkyl-10H-phenothiazine-5-oxides by enantioselective biotransformations

  摘要：

  A series of racemic 10-alkyl-3-formyl-10H-phenothiazine-5-oxides (+/-)-2a-h were subjected to biotransformation with baker's yeast resulting in optically active aldehydes (+)-2a-h and alcohols (-)-3a-h in moderate enantiomeric excess. The racemic 10-alkyl-3-hydroxymethyl-10H-phenothiazine-5-oxides (+/-)-3a-h and 3-acetoxymethyl-10-alkyl-10H-phenothiazine-5-oxides (+/-)-4a-h obtained from the racemic aldehydes ()-2a-h were also tested in enantioselective lipase-catalyzed acetylations and alcoholysis reactions. The highest enantiomeric purities were achieved by a Novozyme 435-catalyzed acetylation-ethanolysis sequence, leading to optically active alcohols (-)-3a h in 83-92% e.e. A novel NMR method using enantiopure dibenzoyl tartaric acid as chiral additive was developed for determination of the enantiomeric composition of the optically active products. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00077-0

文献信息

• Elucidating the Structure-Reactivity Correlations of Phenothiazine-Based Fluorescent Probes toward ClO⁻
  作者：Shichao Wang、Boyu Zhang、Wenjing Wang、Gang Feng、Daqiang Yuan、Xuanjun Zhang

  DOI：10.1002/chem.201800356

  日期：2018.6.7

  In this work, with the aim of developing effective molecular probes and investigating the structure–reactivity correlation, a short series of phenothiazine‐based fluorescent probes are designed for the detection of ClO− with differing electron push‐pull groups. Sensing experiment results and single‐crystal X‐ray analysis with the aid of time‐dependent DFT (TD‐DFT) calculations reveal that substituting

  在这项工作中，与开发有效的分子探针和调查结构反应性相关的目的，一个短系列吩噻嗪系荧光探针被设计用于检测的CLO -具有不同电子推挽基。传感实验结果和基于时间依赖DFT（TD-DFT）计算的单晶X射线分析表明，具有吸电子能力增强的取代基可以增加吩噻嗪部分的二面角并降低苯并噻嗪的能隙探针，导致增强的朝向CLO反应- 。无论PT1和PT2显示在检测CLO的双色切换- 。PT1带有强供电子基噻吩的化合物显示出从鲑鱼色到蓝色的荧光颜色转换。带有中等电子给体/接受基团的苯并噻唑的PT2的荧光颜色从红色变为绿色。然而，无论PT1和PT2表明几乎没有响应ONOO - 。通过引入与氰基合强吸电子酮，PT3示出在检测到的CLO青色发射-在检测ONOO的和红色发射弱- 。HRMS和1 H NMR结果证实PT1和PT2具有相同的感测模式，在该吩噻嗪的二价硫可以被氧化由C10至亚砜- 。一旦与CLO反应- ，PT3