10-ethynylphenothiazine | 943032-47-1

• 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-ethynylphenothiazine
• 英文别名: 10-ethynyl-10H-phenothiazine；10-Ethynylphenothiazine
• CAS: 943032-47-1
• 化学式: C₁₄H₉NS
• 分子量: 223.298
• InChiKey: JFKSIQOADGVPRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-ethynylphenothiazine 在 四甲基乙二胺 、 双氧水 、 copper(l) chloride 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 34.0h， 生成 5-hydroxy-1-(phenothiazine-5-oxide-10-yl)-1,3-pentadiyne
  参考文献：
  名称：

  Solid State Polymerization of Diacetylenes Incorporating Ynamine Moiety

  摘要：

  Novel ynamine. compounds, 5-hydroxy-1-(phenothiazine-10-yl)-1,3-pentadiyne (1), its S-oxide (2) and S-dioxide (3), were prepared. Compound 2 was found to show thermal reactivity to give polydiacetylene, however 1 and 3 did not show any reactivity. Compound 2 stacks along the c axis, forming a columnar structure. The condition of molecular arrangement satisfied Baughman's criterion. Significant intermolecular contact between the oxygen atoms of sulfoxide groups and the adjacent sulfur atoms was recognized.

  DOI：

  10.1080/15421400600786298
• 作为产物：
  描述：

  10-(1,2,2-trichloroethenyl)phenothiazine 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成 10-ethynylphenothiazine
  参考文献：
  名称：

  Solid State Polymerization of Diacetylenes Incorporating Ynamine Moiety

  摘要：

  Novel ynamine. compounds, 5-hydroxy-1-(phenothiazine-10-yl)-1,3-pentadiyne (1), its S-oxide (2) and S-dioxide (3), were prepared. Compound 2 was found to show thermal reactivity to give polydiacetylene, however 1 and 3 did not show any reactivity. Compound 2 stacks along the c axis, forming a columnar structure. The condition of molecular arrangement satisfied Baughman's criterion. Significant intermolecular contact between the oxygen atoms of sulfoxide groups and the adjacent sulfur atoms was recognized.

  DOI：

  10.1080/15421400600786298

文献信息

• Transannular S...N interactions in 10-ethynyl-10<i>H</i>-phenothiazine 5-oxide and 5,5-dioxide
  作者：Satoru Umezono、Satoshi Ikeda、Tsunehisa Okuno

  DOI：10.1107/s0108270113031661

  日期：2013.12.1

  The title compounds, C₁₄H₉NOS, (1), and C₁₄H₉NO₂S, (2), are oxidation products of the parent compound 10-ethynyl-10H-phenothiazine. They differ with respect to transannular interactions, the intramolecular S...N contact being shorter in (2). Intermolecular Csp—H...O hydrogen bonds were detected in both crystals, and (1) was found to form stronger hydrogen bonds. These results are in agreement with the lower acidity of Csp—H in (2), caused by an increase in π-electron density due to the transannular S...N interaction.

  标题化合物 C14H9NOS（1）和 C14H9NO2S（2）是母体化合物 10-乙炔基-10H-吩噻嗪的氧化产物。它们在跨annular 相互作用方面有所不同，(2) 中分子内 S...N 接触较短。在这两种晶体中都检测到了分子间的 Csp-H...O 氢键，并发现 (1) 形成的氢键更强。这些结果与(2)中 Csp-H 的酸度较低相一致，这是因为跨annular S...N 相互作用增加了 π 电子密度。
• Solid State Polymerization of Diacetylenes Incorporating Ynamine Moiety
  作者：Tsunehisa Okuno、Satoshi Ikeda、Natsuki Kubo、Daniel J. Sandman

  DOI：10.1080/15421400600786298

  日期：2006.10.1

  Novel ynamine. compounds, 5-hydroxy-1-(phenothiazine-10-yl)-1,3-pentadiyne (1), its S-oxide (2) and S-dioxide (3), were prepared. Compound 2 was found to show thermal reactivity to give polydiacetylene, however 1 and 3 did not show any reactivity. Compound 2 stacks along the c axis, forming a columnar structure. The condition of molecular arrangement satisfied Baughman's criterion. Significant intermolecular contact between the oxygen atoms of sulfoxide groups and the adjacent sulfur atoms was recognized.