2,6,2'',6''-tetrakis(mercaptomethyl)-1,1':3',1''-terphenyl | 124561-69-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6,2'',6''-tetrakis(mercaptomethyl)-1,1':3',1''-terphenyl
• 英文别名: [2-[3-[2,6-Bis(sulfanylmethyl)phenyl]phenyl]-3-(sulfanylmethyl)phenyl]methanethiol
• CAS: 124561-69-9
• 化学式: C₂₂H₂₂S₄
• 分子量: 414.681
• InChiKey: DPESQDQAWKDEEY-UHFFFAOYSA-N

物化性质

• 沸点：
  648.4±55.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  4
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6,2'',6''-tetrakis(mercaptomethyl)-1,1':3',1''-terphenyl 在 sodium methylate 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 7H,8H,9H,11H-1,15-(Methanothiomethanothiomethano)-16,20-metheno-5H-dibenzo(1,5)dithiacyclohexadecin-8-one
  参考文献：
  名称：

  Cyclic ketones via the reaction of dithiols with 1,3-dichloroacetone. An unexpected base-catalyzed rearrangement of .alpha.,.alpha.'-dithia ketones

  摘要：

  The reaction of dithiols with 1,3-dichloroacetone under high dilution and catalyzed by cesium carbonate in DMF affords macrocyclic ketones in good yield. Examples of functionalized cyclophanes prepared in this way include 10, 15, 16, 19, 21, and 24. With NaOMe/MeOH as the base, dithiol 14 gave ring-contracted ketone 17 in low yield, in addition to the expected 15 and 16. Ketone 17 was the sole product, in good yield, from 14 and 1,1-dichloroacetone. NaOMe/MeOH also brought about the novel ring contraction of 10 to 11 and 11 to 12. X-ray structures of 10,12,16,19, and 21 are briefly described. Possible mechanisms for the formation of 17 from 14 and for the rearrangement of 10 --> 11 --> 12 are discussed.

  DOI：

  10.1021/jo00058a042
• 作为产物：
  描述：

  2-(6,2'',6''-Tris-carbamimidoylsulfanylmethyl-[1,1';3',1'']terphenyl-2-ylmethyl)-isothiourea; hydrobromide 在 氢氧化钾 作用下， 反应 12.0h， 以46%的产率得到2,6,2'',6''-tetrakis(mercaptomethyl)-1,1':3',1''-terphenyl
  参考文献：
  名称：

  Synthesis of cuppedophanes and cappedophanes. Two new classes of cyclophanes with molecular cavities

  摘要：

  DOI：

  10.1021/jo00290a017

文献信息

• Synthesis of two noninterconvertible conformers of a single host. Self-filled and vaulted cappedophanes
  作者：Thottumkara K. Vinod、Harold Hart

  DOI：10.1021/ja00164a077

  日期：1990.4

  La synthese de deux conformeres de l'α-methyl m-phenylene p-phenylenedioxy tetrathia [3 4 ] metacyclophane est effectuee a partir de l'acetate de dibromo-3,5 phenyle, de tetrakis-mercaptomethyl terphenyle et de bis-bromomethyl-1,4 benzene

  La 合成 de deux conformeres de l'α-methyl m-phenylene p-phenylenedioxy tetrathia [3 4 ] metacyclophane est effectuee a partir de l'acetate de dibromo-3,5 phenyle, de tetrakis-mercaptomethyl terphenyle et de bis-bromomethyl- 1,4苯
• Synthesis of cuppedophanes and cappedophanes. Two new classes of cyclophanes with molecular cavities
  作者：Thottumkara Vinod、Harold Hart

  DOI：10.1021/jo00290a017

  日期：1990.2
• Cyclic ketones via the reaction of dithiols with 1,3-dichloroacetone. An unexpected base-catalyzed rearrangement of .alpha.,.alpha.'-dithia ketones
  作者：Jer Jye Chiu、Rupinder S. Grewal、Harold Hart、Donald L. Ward

  DOI：10.1021/jo00058a042

  日期：1993.3

  The reaction of dithiols with 1,3-dichloroacetone under high dilution and catalyzed by cesium carbonate in DMF affords macrocyclic ketones in good yield. Examples of functionalized cyclophanes prepared in this way include 10, 15, 16, 19, 21, and 24. With NaOMe/MeOH as the base, dithiol 14 gave ring-contracted ketone 17 in low yield, in addition to the expected 15 and 16. Ketone 17 was the sole product, in good yield, from 14 and 1,1-dichloroacetone. NaOMe/MeOH also brought about the novel ring contraction of 10 to 11 and 11 to 12. X-ray structures of 10,12,16,19, and 21 are briefly described. Possible mechanisms for the formation of 17 from 14 and for the rearrangement of 10 --> 11 --> 12 are discussed.