(+/-)-(10-butyl-5-oxo-5,10-dihydro-5λ⁴-phenothiazin-3-yl)methanol | 459454-44-5

• 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-butyl-5-oxo-5,10-dihydro-5λ⁴-phenothiazin-3-yl)methanol
• 英文别名: (10-Butyl-5-oxophenothiazin-3-yl)methanol；(10-butyl-5-oxophenothiazin-3-yl)methanol
• CAS: 459454-44-5；459454-65-0；459454-72-9
• 化学式: C₁₇H₁₉NO₂S
• 分子量: 301.409
• InChiKey: LPFRGNYRNVPIQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  70.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 (+/-)-(10-butyl-5-oxo-5,10-dihydro-5λ⁴-phenothiazin-3-yl)methanol 在 lipase AK 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以91%的产率得到(+/-)-methyl (10-butyl-5-oxo-5,10-dihydro-5λ⁴-phenothiazin-3-yl)acetate
  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-butyl-10H-phenothiazine-3-carbaldehyde 在 sodium tetrahydroborate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (+/-)-(10-butyl-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

文献信息

• Synthesis of optically active 3-substituted-10-alkyl-10H-phenothiazine-5-oxides by enantioselective biotransformations
  作者：Monica Toşa、Csaba Paizs、Cornelia Majdik、Lajos Novák、Pál Kolonits、Florin-Dan Irimie、László Poppe

  DOI：10.1016/s0957-4166(02)00077-0

  日期：2002.2

  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.