10-(prop-1-yn-1-yl)-10H-phenothiazine 5,5-dioxide | 25206-50-2

• 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-(prop-1-yn-1-yl)-10H-phenothiazine 5,5-dioxide
• 英文别名: N(10)-1-propynylphenothiazine-S,S-dioxide；10-Prop-1-ynylphenothiazine 5,5-dioxide；10-prop-1-ynylphenothiazine 5,5-dioxide
• CAS: 25206-50-2
• 化学式: C₁₅H₁₁NO₂S
• 分子量: 269.324
• InChiKey: YZAIHOYAKYOCNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  10-(prop-1-yn-1-yl)-10H-phenothiazine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以56%的产率得到10-(prop-1-yn-1-yl)-10H-phenothiazine 5,5-dioxide
  参考文献：
  名称：

  Crystal structure and anomalous chemical shift of 10-(prop-1-yn-1-yl)-10H-phenothiazine 5,5-dioxide: Intramolecular S⋯N transannular effect

  摘要：

  The novel ynamine compounds, 10-(prop-1-yn-1-yl)-10H-phenothiazine 5-oxide (2) and 10-(prop-1-yn-1-yl)-10H-phenothiazine 5,5-dioxide (3), were prepared by MCPBA oxidation of 10-(prop-1-yn-1-yl)-10H-phenothiazine (1). These compounds were characterized successfully by crystallographical analyses, H-1 and C-13 NMR. The H-1 NMR signals of 2 showed downfield shifts compared with 1 as expected. However two kinds of signals, methyl and 1,9-position of 3, indicated upfield shifts compared with 2. These anomalous upfield shifts were reasonably explained by trans-annular S center dot center dot center dot N interaction and by increase of electron density on the nitrogen atom. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.06.045

文献信息

• Crystal structure and anomalous chemical shift of 10-(prop-1-yn-1-yl)-10H-phenothiazine 5,5-dioxide: Intramolecular S⋯N transannular effect
  作者：Satoru Umezono、Tsunehisa Okuno

  DOI：10.1016/j.molstruc.2013.06.045

  日期：2013.10

  The novel ynamine compounds, 10-(prop-1-yn-1-yl)-10H-phenothiazine 5-oxide (2) and 10-(prop-1-yn-1-yl)-10H-phenothiazine 5,5-dioxide (3), were prepared by MCPBA oxidation of 10-(prop-1-yn-1-yl)-10H-phenothiazine (1). These compounds were characterized successfully by crystallographical analyses, H-1 and C-13 NMR. The H-1 NMR signals of 2 showed downfield shifts compared with 1 as expected. However two kinds of signals, methyl and 1,9-position of 3, indicated upfield shifts compared with 2. These anomalous upfield shifts were reasonably explained by trans-annular S center dot center dot center dot N interaction and by increase of electron density on the nitrogen atom. (c) 2013 Elsevier B.V. All rights reserved.