2-(1-Mercaptomethyl-2-phenoxy-ethylsulfanyl)-3-phenoxy-propane-1-thiol | 178539-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(1-Mercaptomethyl-2-phenoxy-ethylsulfanyl)-3-phenoxy-propane-1-thiol
• CAS: 178539-26-9
• 化学式: C₁₈H₂₂O₂S₃
• 分子量: 366.569
• InChiKey: HQOGRAGEQAQSAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  23.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.46
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  顺式-1,4-二氯-2-丁烯 、 2-(1-Mercaptomethyl-2-phenoxy-ethylsulfanyl)-3-phenoxy-propane-1-thiol 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以13.5%的产率得到3,5-Bis-(phenoxymethylen)-1,4,7-trithia-cycloundec-9-en
  参考文献：
  名称：

  Bis-(1-chlor-3-phenoxy-prop-2-yl)-sulfane - Nucleophile Substitution und Regiochemie, Diastereomerentrennung und -zuordnung. Synthese diastereomerenreiner Trithiacyclen

  摘要：

  The title compounds 1 were substituted by a series of O-, N- and S-nucleophiles (H(2)0 solvolysis, AgOAc, NaN3, KSCN, NaSPh, thiourea). A strong tendency to beta-elimination of HCl depending on the kind of the attacking nucleophile was found. In most cases no regioisomerization could be detected in the isolated products of the nucleophilic displacement. Best results were obtained with sulfur nucleophiles. The separation of the diastereomeric mixture of the p-kresyl derivative 1b into the individual diastereomers 1bA and 1bB in a preparative scale was achieved. These 3-thia1,5-dichlorides and several products of substitution could be assigned to the meso- or (+/-)-form by examination of the stereochemistry and symmetry of the corresponding sulfoxides.The 1,5-dimercapto derivatives 8 are convenient as structural units for the synthesis of diastereomerically pure cis- or trans-disubstituted trithiacycles e.g. 15bA, 15bB. The (+/-)-form of the 4,6-disubstituted 2,5,8-trithia[9]-(2,6)-pyridinophane 16bA was characterized by X-ray crystal structure determination.

  DOI：

  10.1002/prac.19963380165
• 作为产物：
  描述：

  Bis-(1-chlor-3-phenoxy-prop-2-yl)-sulfan 在 硫脲 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以84%的产率得到2-(1-Mercaptomethyl-2-phenoxy-ethylsulfanyl)-3-phenoxy-propane-1-thiol
  参考文献：
  名称：

  Bis-(1-chlor-3-phenoxy-prop-2-yl)-sulfane - Nucleophile Substitution und Regiochemie, Diastereomerentrennung und -zuordnung. Synthese diastereomerenreiner Trithiacyclen

  摘要：

  The title compounds 1 were substituted by a series of O-, N- and S-nucleophiles (H(2)0 solvolysis, AgOAc, NaN3, KSCN, NaSPh, thiourea). A strong tendency to beta-elimination of HCl depending on the kind of the attacking nucleophile was found. In most cases no regioisomerization could be detected in the isolated products of the nucleophilic displacement. Best results were obtained with sulfur nucleophiles. The separation of the diastereomeric mixture of the p-kresyl derivative 1b into the individual diastereomers 1bA and 1bB in a preparative scale was achieved. These 3-thia1,5-dichlorides and several products of substitution could be assigned to the meso- or (+/-)-form by examination of the stereochemistry and symmetry of the corresponding sulfoxides.The 1,5-dimercapto derivatives 8 are convenient as structural units for the synthesis of diastereomerically pure cis- or trans-disubstituted trithiacycles e.g. 15bA, 15bB. The (+/-)-form of the 4,6-disubstituted 2,5,8-trithia[9]-(2,6)-pyridinophane 16bA was characterized by X-ray crystal structure determination.

  DOI：

  10.1002/prac.19963380165