10-n-heptylphenothiazine-3-carbaldehyde

• 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-n-heptylphenothiazine-3-carbaldehyde
• 英文别名: 10-Heptylphenothiazine-3-carbaldehyde；10-heptylphenothiazine-3-carbaldehyde
• 化学式: C₂₀H₂₃NOS
• 分子量: 325.475
• InChiKey: ZJSPRYJHEQYCTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-n-heptylphenothiazine-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-heptyl-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：

  1-溴代庚烷 在 sodium hydroxide 、 三氯氧磷 作用下， 以 二甲基亚砜 为溶剂， 生成 10-n-heptylphenothiazine-3-carbaldehyde
  参考文献：
  名称：

  具有不同烷基链长度的AIE活性9,10-双（N-烷基苯硫噻嗪-3-基-乙烯基-2）蒽的压电荧光色性质

  摘要：

  具有不同碳数（n）烷基链的n  ，9,10-双（N-烷基吩噻嗪-3-基-乙烯基-2）蒽（PT - C n）（n = 2，3，5，6，6，7，9，制备12、18）以进一步理解烷基长度对含烷基的9，10-双（芳基乙烯基）蒽的固态荧光和压致变色发光的影响。结果表明，受压和退火的PT - C n的荧光发射都逐渐蓝移，但是随着烷基长度的增加，退火态的蓝移幅度更加显着，从而导致含烷基的PT-更长。ç ñ显示更大的压电氟致变色（PFC）光谱偏移。粉末广角X射线衍射和差示扫描量热法实验表明，在各种外部刺激下晶态和非晶态之间的转变是PFC和恢复行为的原因。这项工作再次证明，结合分子化学结构的简单改变和外部刺激下聚集体形态的物理变化，可以调节某些有机荧光团的固态光学性质。

  DOI：

  10.1016/j.dyepig.2013.10.020

文献信息

• Biocatalytic enantioselective preparation of phenothiazine-based cyanohydrin acetates: kinetic and dynamic kinetic resolution
  作者：Csaba Paizs、Petri Tähtinen、Monica Toşa、Cornelia Majdik、Florin-Dan Irimie、Liisa T. Kanerva

  DOI：10.1016/j.tet.2004.06.136

  日期：2004.11

  resolution is used for the preparation of a series of novel (+)-10-alkyl-phenothiazin-3-ylcyanomethyl acetates. The method exploits a basic resin both for the racemization and formation of phenothiazine-based cyanohydrins and for the decomposition of acetone cyanohydrin in one pot together with Candida antarctica lipase A-catalyzed enantioselective acylation with vinyl acetate in acetonitrile. The Candida

  动态动力学拆分用于制备一系列新型（+）-10-烷基-吩噻嗪-3-基氰基乙酸甲酯。该方法利用碱性树脂在一个锅中外消旋和形成吩噻嗪基氰醇，并与丙酮念珠菌脂肪酶A一起催化乙腈中乙酸乙烯酯的对映选择性酰化反应，从而分解丙酮氰醇。的南极假丝酵母脂肪酶的外消旋的催化甲醇分解10烷基吩噻嗪-3- ylcyanomethyl乙酸盐在乙腈中与ë »100导致相应的（ - ） -乙酸盐。
• Synthesis, photophysical and electrochemical properties of stilbenoid dendrimers with phenothiazine surface group
  作者：Chinnadurai Satheeshkumar、Mahalingam Ravivarma、Perumal Rajakumar、Rajamani Ashokkumar、Dong-Cheol Jeong、Changsik Song

  DOI：10.1016/j.tetlet.2014.11.088

  日期：2015.1

  Synthesis of some novel stilbenoid dendrimers with the phenothiazine surface group has been achieved using Horner–Wadsworth–Emmons (HWE) and click reactions through convergent methodology. Alkyl chains have been incorporated at the periphery of phenothiazine moiety to enhance the solubility of the dendrimers. The photophysical properties indicate an increase in the molar extinction coefficient, fluorescence

  使用Horner-Wadsworth-Emmons（HWE）并通过聚合方法进行点击反应，已经实现了一些具有吩噻嗪表面基团的新型二苯乙烯类树状大分子的合成。已在吩噻嗪部分的外围引入了烷基链以增强树枝状聚合物的溶解性。光物理性质表明，随着树枝状聚合物的生成增加，摩尔消光系数，荧光量子产率和寿命增加。较高的荧光量子产率表明二苯乙烯单元的反式几何形状。
• Piezofluorochromic properties of AIE-active 9,10-bis(N-alkylpheno-thiazin-3-yl-vinyl-2)anthracenes with different length of alkyl chains
  作者：Meng Zheng、Mingxiao Sun、Yiping Li、Jianfeng Wang、Lingyu Bu、Shanfeng Xue、Wenjun Yang

  DOI：10.1016/j.dyepig.2013.10.020

  日期：2014.3

  9,10-Bis(N-alkylphenothiazin-3-yl-vinyl-2)anthracenes (PT-Cn) with different carbon numbers (n) of alkyl chains (n = 2, 3, 5, 6, 7, 9, 12, 18) are prepared to further understand the effect of alkyl lengths on the solid-state fluorescence and piezochromic luminescence of alkyl-containing 9,10-bis(arylvinyl)anthracenes. The results show that the fluorescence emissions of both pressed and annealed PT-Cn

  具有不同碳数（n）烷基链的n  ，9,10-双（N-烷基吩噻嗪-3-基-乙烯基-2）蒽（PT - C n）（n = 2，3，5，6，6，7，9，制备12、18）以进一步理解烷基长度对含烷基的9，10-双（芳基乙烯基）蒽的固态荧光和压致变色发光的影响。结果表明，受压和退火的PT - C n的荧光发射都逐渐蓝移，但是随着烷基长度的增加，退火态的蓝移幅度更加显着，从而导致含烷基的PT-更长。ç ñ显示更大的压电氟致变色（PFC）光谱偏移。粉末广角X射线衍射和差示扫描量热法实验表明，在各种外部刺激下晶态和非晶态之间的转变是PFC和恢复行为的原因。这项工作再次证明，结合分子化学结构的简单改变和外部刺激下聚集体形态的物理变化，可以调节某些有机荧光团的固态光学性质。
• 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.