10-(prop-1-yn-1-yl)-10H-phenothiazine | 4282-90-0

• 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
• 英文别名: N-(1-propynyl)phenothiazine；10-propynylphenothiazine；10-prop-1-ynyl-10H-phenothiazine；10-prop-1-ynyl-phenothiazine；10-Prop-1-inyl-phenothiazin；10--phenothiazin；n-Propynyl-phenothiazine；10-prop-1-ynylphenothiazine
• CAS: 4282-90-0
• 化学式: C₁₅H₁₁NS
• 分子量: 237.325
• InChiKey: XPAKUJKFJVVHHY-UHFFFAOYSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  368.0±35.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 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：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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 2.0h， 以42%的产率得到10-(prop-1-yn-1-yl)-10H-phenothiazine 5-oxide
  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
• 作为产物：
  描述：

  吩噻嗪 、 3-溴丙炔 生成 10-(prop-1-yn-1-yl)-10H-phenothiazine
  参考文献：
  名称：

  Notes: An Unusual Reaction of Propargyl Bromide

  摘要：

  DOI：

  10.1021/jo01103a617

文献信息

• Ring Expansion of Spirocyclic Cyclobutenylidene Ligands in Pentacarbonylchromium Complexes to Tetrahydroindene Derivatives
  作者：Helmut Fischer、Christoph C. Karl、Gerhard Roth

  DOI：10.1002/cber.19961290605

  日期：1996.6

  bond of the vinylidene ligand of 1. Initially, complexes with a spirocyclic cyclobutenylidene ligand are formed, [(CO)5Cr(CH2)5] (3) and [(CO)5-Cr(CH2)5] (10). Subsequent thermally initiated ring expansion affords the 2-methyl-4,5,6,7-tetrahydroindenyl(methyl)thioether complex [(CO)5-Cr–S(Me)(Me-C9H10)] (4) and the N-(2-methyl-4,5,6,7-tetrahydroindenyl)phenothiazine complex [(CO)5Cr–S(C6H4)2-N–(Me-C9H10)]

  五羰基（五亚甲基亚乙烯基）铬[[CO）5 CrCC（CH 2）5 ]（1）通过区域特异性与1-甲硫基-1-丙炔（2a）和N-（1-丙炔基）吩噻嗪（2b）反应炔的CC键与1的亚乙烯基配体的CC键的加成。最初，形成具有螺环的环丁烯基配体的配合物，[（CO）5 Cr（CH 2）5 ]（3）和[（CO）5 -Cr（CH 2）5 ]（10）。随后的热引发的扩环提供了2-甲基-4,5,6,7-四氢茚基（甲基）硫醚配合物[（CO）5 -Cr–S（Me）（Me-C 9 H 10）]（4）和的ñ - （2-甲基-4,5,6,7-四氢茚基）吩噻嗪配合物[（CO）5的Cr-S（C 6 H ^ 4）2 -N-（ME-C 9 H ^ 10）]（11） ， 分别。在两种配合物4和11中，配体均通过硫原子与金属配位。通过（H，H）-，（H，C）-和NOE-相关的NMR光谱确定结构。在反应1中与2a一起，除3和4外，还形
• Himbert,G.; Regitz,M., Justus Liebigs Annalen der Chemie, 1973, p. 1505 - 1529
  作者：Himbert,G.、Regitz,M.

  DOI：——

  日期：——
• Regitz M.; Arnold, B.; Danion, D., Bulletin des Societes Chimiques Belges, 1981, vol. 90, # 6, p. 615 - 632
  作者：Regitz M.、Arnold, B.、Danion, D.、Schubert, H.、Fusser, G.

  DOI：——

  日期：——
• Anomalous planar structure observed in (E)-10-(1,2-dibromoprop-1-en-1-yl)-10H-phenothiazine
  作者：Satoru Umezono、Tsunehisa Okuno

  DOI：10.1016/j.molstruc.2014.11.066

  日期：2015.3

  Both Z and E isomers of 10-(1,2-dibromoprop-1-en-1-yl)-10H-phenothiazine were given by bromine addition to 10-(prop-1-yn-1-yl)-10H-phenothiazine with little stereoselectivity. The crystal structure of the Z isomer showed a usual butterfly structure, while that of the E isomer afforded an anomalous planar structure which was usually observed in positively charged phenothiazines. The reason for the planar structure was concluded to originate in intermolecular charge transfer interaction through the C-Br center dot center dot center dot pi halogen bonds. (C) 2014 Elsevier B.V. All rights reserved.
• Kosack, Steffen; Himbert, Gerhard, Chemische Berichte, 1988, vol. 121, p. 833 - 842
  作者：Kosack, Steffen、Himbert, Gerhard

  DOI：——

  日期：——

表征谱图