(S)-3-methyl-3,4-dihydro-2H-[1,4]benzothiazine | 1185454-10-7

• 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: (S)-3-methyl-3,4-dihydro-2H-[1,4]benzothiazine
• 英文别名: (3S)-3,4-dihydro-3-methyl-2H-[1,4]benzothiazine；(S)-3,4-dihydro-3-methyl-2H-[1,4]benzothiazine；(3S)-3-methyl-3,4-dihydro-2H-1,4-benzothiazine
• CAS: 1185454-10-7
• 化学式: C₉H₁₁NS
• 分子量: 165.259
• InChiKey: OFUZAVQYAIEYET-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-methyl-3,4-dihydro-2H-[1,4]benzothiazine 在 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (3S)-4-{6-[2-acetamido-9-(2-acetoxyethoxy)methylpurin-6-yl]aminohexanoyl}-3,4-dihydro-3-methyl-2H-[1,4]benzothiazine
  参考文献：
  名称：

  手性杂环胺的N- [ω-（嘌呤-6-基）氨基链烷酰基]衍生物作为有希望的抗疱疹病毒药物

  摘要：

  合成了具有手性杂环胺的新型嘌呤和2-氨基嘌呤共轭物，它们通过ω-氨基烷酰基片段在C-6处连接。获得的化合物对1型单纯疱疹病毒（HSV-1）和对阿昔洛韦具有抗药性的HSV-1菌株均表现出抑制活性。合成化合物的抗疱疹病毒活性取决于其立体构型。

  DOI：

  10.1002/ejoc.201900727
• 作为产物：
  描述：

  2-溴硫代苯酚 在 copper(l) iodide 、 sodium hydride 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 48.0h， 生成 (S)-3-methyl-3,4-dihydro-2H-[1,4]benzothiazine
  参考文献：
  名称：

  A convenient synthesis of chiral amino acid derived 3,4-dihydro-2H-benzo[b][1,4]thiazines and antibiotic levofloxacin

  摘要：

  A series of 3,4-dihydro-2H-benzo[b](1,4]thiazine derivatives 8a-g were synthesized via- a copper-catalyzed intramolecular N-aryl amination reaction on substituted 2-(2-bromophenylthio)-ethanamines which were synthesized by the nucleophilic substitution reaction of 2-bromobenzenethiol with Boc-protected amino alcohol derivatives. This strategy provides a short and an efficient entry to (S)-3-methyl-1,4-benzoxazine 12, an advanced synthetic intermediate for the synthesis of levofloxacin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.05.104

文献信息

• Synthesis of enantiomers of 3-methyl- and 3-phenyl-3,4-dihydro-2H-[1,4]benzothiazines and their 1,1-dioxides via an acylative kinetic resolution protocol
  作者：Dmitry A. Gruzdev、Evgeny N. Chulakov、Liliya Sh. Sadretdinova、Mikhail I. Kodess、Galina L. Levit、Victor P. Krasnov

  DOI：10.1016/j.tetasy.2015.01.010

  日期：2015.2

  (ee >97%). This method proved to be less suitable for the preparation of the (S)-enantiomer of 3,4-dihydro-3-phenyl-2H-[1,4]benzothiazine (ee up to 93%) and its sulfone (ee 82%) which were both obtained in low yields. The loss of enantioselectivity for (S)-3,4-dihydro-3-phenyl-2H-[1,4]benzothiazine and its sulfone occurred during hydrolysis of the corresponding diastereoisomerically pure amides.

  已经发现，（的酰氯小号） -萘普生，Ñ -phthaloyl-（小号） -亮氨酸，和Ñ甲苯磺酰基（小号） -脯氨酸是外消旋的3-甲基的acylative动力学拆分高效手性拆分试剂和3-苯基-3,4-二氢-3-甲基-2 ħ - [1,4]苯并噻嗪。基于该实验结果，包括acylative动力学拆分制备性协议，随后通过单个（主）非对映体酰胺和酰胺键的随后水解分离，提出了。使用与各种手性拆分剂该方法中，（小号） -和（- [R）3,4-二氢-3-甲基-2 -对映体ħ-得到[1,4]苯并噻嗪（EE> 99％）。酰胺的非对映体相应的氧化，随后导致了（脱酰小号） -和（- [R ）-对映体的3,4-二氢-3-甲基-2 ħ - [1,4]苯并噻嗪1,1-二氧化钛（ee值> 97％）。这种方法被证明是不适合的（制备小号）3,4-二氢-3-苯基-2 -对映体ħ - [1,4]苯并噻嗪（EE高达93％）和它的砜（EE
• N-Tosyl-(S)-Prolyl Chloride in Kinetic Resolution of Racemic Heterocyclic Amines
  作者：D. A. Gruzdev、S. A. Vakarov、G. L. Levit、V. P. Krasnov

  DOI：10.1007/s10593-014-1432-4

  日期：2014.3

  The kinetic resolution of racemic heterocyclic amines via acylation with N-tosyl-(S)-prolyl chloride was systematically investigated. It was established that racemic mixtures of aromatic amines could be resolved with high efficiency, while the acylation of 2- and 3-methylpiperidines occurred with low diastereoselectivity. A method for the preparation of enantiomerically pure (3R)-7,8-difluoro-3-methyl-3

  系统研究了外消旋杂环胺经N-甲苯磺酰基-（S）-脯氨酰氯酰化的动力学拆分。已经确定，芳族胺的外消旋混合物可以高效分离，而2-和3-甲基哌啶的酰化则以低的非对映选择性发生。开发了制备对映体纯的（3 R）-7,8-二氟-3-甲基-3,4-二氢-2 H- [1,4]苯并恶嗪的方法。
• Acylative kinetic resolution of racemic heterocyclic amines with (R)-2-phenoxypropionyl chloride
  作者：Sergey A. Vakarov、Dmitry A. Gruzdev、Evgeny N. Chulakov、Liliya Sh. Sadretdinova、Andrey A. Tumashov、Marina G. Pervova、Marina A. Ezhikova、Mikhail I. Kodess、Galina L. Levit、Victor P. Krasnov、Valery N. Charushin

  DOI：10.1016/j.tetasy.2016.10.004

  日期：2016.12

  The acylative kinetic resolution of racemic heterocyclic amines such as 3,4-dihydro-3-methyl-2H-[1,4] benzoxazines, 3,4-dihydro-3-methyl-2H-[1,4]benzothiazine, 2-methyl-1,2,3,4-tetrahydro-quinolines and 2-methylindoline with enantiopure (R)-2-phenoxypropionyl chloride has been studied. It has been found that acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzothiazine proceeds with the best stereoselectively when compared with other racemic amines. An efficient method for the preparation of (S)-3,4-dihydro-3-methyl-2H-[1,4]benzothiazine (99.4% ee) via a kinetic resolution protocol was developed. The possibility of recycling (R)-2-phenoxypropionic acid has been demonstrated. (C) 2016 Elsevier Ltd. All rights reserved.