[6-(Sulfanylmethyl)phenoxathiin-4-yl]methanethiol | 1380673-29-9

• 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: [6-(Sulfanylmethyl)phenoxathiin-4-yl]methanethiol
• 英文别名: [6-(sulfanylmethyl)phenoxathiin-4-yl]methanethiol
• CAS: 1380673-29-9
• 化学式: C₁₄H₁₂OS₃
• 分子量: 292.447
• InChiKey: IIZZNKQCODBYFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  36.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [6-(Sulfanylmethyl)phenoxathiin-4-yl]methanethiol 、 丁基三氯化锡 在 1,4-diazabicyclo[2.2.2]octane 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到[S(C6H3CH2S)2O]SnCl(n-Bu)
  参考文献：
  名称：

  Structural differences in eight- and ten-membered heterocyclic tin compounds displaying transannular interactions O⋯Sn: An experimental and theoretical study

  摘要：

  Two series of heterocyclic tin compounds of general formula [(S{C6H3(CH2)(n)S}(2)O)(SnRR2)-R-1] with different central ring sizes were prepared. The ten-membered series includes the compounds with n = 1 and R-1 = R-2 = Ph (5); R-1 = Cl, R-2 = Ph (6); R-1 = Cl, R-2 = n-Bu (7); R-1 = R-2 = Cl (8); the eight-membered series includes the compounds with n = 0 and R-1 = R-2 = Ph (10); R-1 = Cl, R-2 = n-Bu (11) and R-1 = R-2 = Cl (12). The compounds 5, 7, 8, 10, and 11 were investigated by single-crystal X-ray diffraction. The chloro compounds 7, 8, and 11 displayed a bipyramidal geometry at the tin atom with different degrees of distortion ranging from 57% to 62%. The diphenyl compounds 5 and 10 displayed a tetrahedral geometry at Sn. The conformation of the central ring in the ten-membered series is similar and is described as boat; the other series displayed two different conformations described as boat-chair and boat-boat. The possible conformers in the gas state of compounds 5, 7, 8, 10, 11, and 12 were investigated by MMFF, LSDA, BLYP, B3LYP, and M06 functionals using the DGDZVP and TZVP basis sets. The structural data of the total optimization agreed with the experimental results. The topological analysis indicated that bond critical points are present along the O center dot center dot center dot Sn direction in the compounds 7, 8, 11, and 12. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.04.004
• 作为产物：
  描述：

  Phenoxathiine-4,6-dicarbaldehyde 在 sodium tetrahydroborate 、 氢溴酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 52.0h， 生成 [6-(Sulfanylmethyl)phenoxathiin-4-yl]methanethiol
  参考文献：
  名称：

  Structural differences in eight- and ten-membered heterocyclic tin compounds displaying transannular interactions O⋯Sn: An experimental and theoretical study

  摘要：

  Two series of heterocyclic tin compounds of general formula [(S{C6H3(CH2)(n)S}(2)O)(SnRR2)-R-1] with different central ring sizes were prepared. The ten-membered series includes the compounds with n = 1 and R-1 = R-2 = Ph (5); R-1 = Cl, R-2 = Ph (6); R-1 = Cl, R-2 = n-Bu (7); R-1 = R-2 = Cl (8); the eight-membered series includes the compounds with n = 0 and R-1 = R-2 = Ph (10); R-1 = Cl, R-2 = n-Bu (11) and R-1 = R-2 = Cl (12). The compounds 5, 7, 8, 10, and 11 were investigated by single-crystal X-ray diffraction. The chloro compounds 7, 8, and 11 displayed a bipyramidal geometry at the tin atom with different degrees of distortion ranging from 57% to 62%. The diphenyl compounds 5 and 10 displayed a tetrahedral geometry at Sn. The conformation of the central ring in the ten-membered series is similar and is described as boat; the other series displayed two different conformations described as boat-chair and boat-boat. The possible conformers in the gas state of compounds 5, 7, 8, 10, 11, and 12 were investigated by MMFF, LSDA, BLYP, B3LYP, and M06 functionals using the DGDZVP and TZVP basis sets. The structural data of the total optimization agreed with the experimental results. The topological analysis indicated that bond critical points are present along the O center dot center dot center dot Sn direction in the compounds 7, 8, 11, and 12. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.04.004

文献信息

• Structural differences in eight- and ten-membered heterocyclic tin compounds displaying transannular interactions O⋯Sn: An experimental and theoretical study
  作者：Diego Martínez-Otero、Benito Flores-Chávez、José G. Alvarado-Rodríguez、Noemí Andrade-López、Julián Cruz-Borbolla、Thangarasu Pandiyan、Vojtech Jancik、Enrique González-Jiménez、Christiaan Jardinez

  DOI：10.1016/j.poly.2012.04.004

  日期：2012.6

  Two series of heterocyclic tin compounds of general formula [(SC6H3(CH2)(n)S}(2)O)(SnRR2)-R-1] with different central ring sizes were prepared. The ten-membered series includes the compounds with n = 1 and R-1 = R-2 = Ph (5); R-1 = Cl, R-2 = Ph (6); R-1 = Cl, R-2 = n-Bu (7); R-1 = R-2 = Cl (8); the eight-membered series includes the compounds with n = 0 and R-1 = R-2 = Ph (10); R-1 = Cl, R-2 = n-Bu (11) and R-1 = R-2 = Cl (12). The compounds 5, 7, 8, 10, and 11 were investigated by single-crystal X-ray diffraction. The chloro compounds 7, 8, and 11 displayed a bipyramidal geometry at the tin atom with different degrees of distortion ranging from 57% to 62%. The diphenyl compounds 5 and 10 displayed a tetrahedral geometry at Sn. The conformation of the central ring in the ten-membered series is similar and is described as boat; the other series displayed two different conformations described as boat-chair and boat-boat. The possible conformers in the gas state of compounds 5, 7, 8, 10, 11, and 12 were investigated by MMFF, LSDA, BLYP, B3LYP, and M06 functionals using the DGDZVP and TZVP basis sets. The structural data of the total optimization agreed with the experimental results. The topological analysis indicated that bond critical points are present along the O center dot center dot center dot Sn direction in the compounds 7, 8, 11, and 12. (C) 2012 Elsevier Ltd. All rights reserved.