2,10-dichloro-6-bis(2-chloroethyl)amino-4,8-dinitrodibenzo[d,g][1,3,6,2]dioxathiaphosphocin | 478007-63-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,10-dichloro-6-bis(2-chloroethyl)amino-4,8-dinitrodibenzo[d,g][1,3,6,2]dioxathiaphosphocin
• 英文别名: 3,7-dichloro-N,N-bis(2-chloroethyl)-1,9-dinitro-11-oxobenzo[d][1,3,6,2]benzodioxathiaphosphocin-11-amine
• CAS: 478007-63-5
• 化学式: C₁₆H₁₂Cl₄N₃O₇PS
• 分子量: 563.139
• InChiKey: VSROHAWHXDMCKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  125.05
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,10-dichloro-6-bis(2-chloroethyl)amino-4,8-dinitrodibenzo[d,g][1,3,6,2]dioxathiaphosphocin 在 双氧水 、 溶剂黄146 作用下， 反应 3.0h， 以78%的产率得到2,10-dichloro-6-bis(2-chloroethyl)amino-4,8-dinitrodibenzo[d,g][1,3,6,2]dioxathiaphosphocin 6-oxide
  参考文献：
  名称：

  Synthesis and Spectral Studies of 2,10-Dichloro-6-Bis(2-Chloroethyl)Amino-4,8-Dinitrodibenzo[ d , g ][1,3,6,2]-Dioxathiaphosphocin, 2,10-Dichloro-6-Bis(2-Chloroethyl)Amino-4,8-Dinitrodibenzo[ d , g ][1,3,6,2]Dioxathiaphosphocin 6-Oxide, 2-Bis(2-Chloroethyl)Amino-2,3-Dihydro-5-Thiophenoxy-1 H -1,3,2-Benzodiazaphosphole 2-Oxide, 2-Bis(2-Chloroethyl)Amino-1,2,3,4-Tetrahydro-1,3,2-Benzodiazaphosphorinane 2-Oxide, 5-Bromo-5-Nitro-2-Bis(2-Chloroethyl)Amino-1,3,2-Dioxaphosphorinane 2-Oxide, and 8-Bis(2-Chloroethyl)Amino-16 H -Dinaphtho[2,1- d :1′,2′- g ]1,3,2-Dioxaphosphocin 8-Oxide--Potential Anticancer Agents

  摘要：

  Several novel bis(2-chloroethyl)aminophosphoryl-containing compounds have been prepared as potential anticancer agents. 2,10-Dichloro-6-[bis(2-chloroethyl)lamino-4,8-dinitrodibenzo[d,g][1,3,6,2]- dioxathiaphosphocin 6-oxide (5), 2-bis(2-chloroethyl)amino-1,3, 2-dioxaphosphorinane 2-oxide (13), and 8- bis(2-chloroethyl)amino-6H-dinaphtho[2,1-d:1',2]1,3,2-dioxaphosphocin 8-oxide (15) were synthesized from a reaction of equimolar quantities of the corresponding precursor diols 3, 12, and 14 with coreagent N,N-bis(2-chloroethyl)phosphoramidic dichloride (1) at various temperatures in dry toluene/ether in the presence of triethylamine. In addition, 2-bis(2-chloroethyl)amino - 2,3-dihydro-5-thiophenoxy-1H-1,3,2-benzodiazaphosphole 2-oxide (9) and 2-bis(2-chloroethyl)amino-1,2,3,4-tetrahydro-1, 3,2-benzodiazophosphorinane 2-oxide (11) were derived from 4-thiophenoxy-1,2-diphenyldiamine (8) and 2-aminobenzylamine (10) respectively, under similar conditions. Interestingly, attempted oxidation of 5 to the corresponding sulfone 7 by H2O2 (3011) in acetic acid yielded only sulfoxide 6 12,10-dichloro-6-bis(2-chloroethyl)amino-4,8-dinitrodibenzo[d,g][1,3,6,2]dioxathiaphosphocin 6-oxide}. In an alternative approach, oxidation of 5,5'-dichloro-3,3'-dinitro-2,2'-dihydroxydiphenyl sulfide (3) with H2O2 (30%) in acetic acid formed the corresponding sulfone 4. However attempted cyclization of 4 with 1, in the presence of triethylamine, to give the sulfone expected from 5 was unsuccessful. NMR analysis of 6 suggests the presence of two conformers in solution.

  DOI：

  10.1080/10426500210247
• 作为产物：
  描述：

  2,2’-硫代双(4-氯苯酚) 在 硝酸 、 溶剂黄146 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 2,10-dichloro-6-bis(2-chloroethyl)amino-4,8-dinitrodibenzo[d,g][1,3,6,2]dioxathiaphosphocin
  参考文献：
  名称：

  Synthesis and Spectral Studies of 2,10-Dichloro-6-Bis(2-Chloroethyl)Amino-4,8-Dinitrodibenzo[ d , g ][1,3,6,2]-Dioxathiaphosphocin, 2,10-Dichloro-6-Bis(2-Chloroethyl)Amino-4,8-Dinitrodibenzo[ d , g ][1,3,6,2]Dioxathiaphosphocin 6-Oxide, 2-Bis(2-Chloroethyl)Amino-2,3-Dihydro-5-Thiophenoxy-1 H -1,3,2-Benzodiazaphosphole 2-Oxide, 2-Bis(2-Chloroethyl)Amino-1,2,3,4-Tetrahydro-1,3,2-Benzodiazaphosphorinane 2-Oxide, 5-Bromo-5-Nitro-2-Bis(2-Chloroethyl)Amino-1,3,2-Dioxaphosphorinane 2-Oxide, and 8-Bis(2-Chloroethyl)Amino-16 H -Dinaphtho[2,1- d :1′,2′- g ]1,3,2-Dioxaphosphocin 8-Oxide--Potential Anticancer Agents

  摘要：

  Several novel bis(2-chloroethyl)aminophosphoryl-containing compounds have been prepared as potential anticancer agents. 2,10-Dichloro-6-[bis(2-chloroethyl)lamino-4,8-dinitrodibenzo[d,g][1,3,6,2]- dioxathiaphosphocin 6-oxide (5), 2-bis(2-chloroethyl)amino-1,3, 2-dioxaphosphorinane 2-oxide (13), and 8- bis(2-chloroethyl)amino-6H-dinaphtho[2,1-d:1',2]1,3,2-dioxaphosphocin 8-oxide (15) were synthesized from a reaction of equimolar quantities of the corresponding precursor diols 3, 12, and 14 with coreagent N,N-bis(2-chloroethyl)phosphoramidic dichloride (1) at various temperatures in dry toluene/ether in the presence of triethylamine. In addition, 2-bis(2-chloroethyl)amino - 2,3-dihydro-5-thiophenoxy-1H-1,3,2-benzodiazaphosphole 2-oxide (9) and 2-bis(2-chloroethyl)amino-1,2,3,4-tetrahydro-1, 3,2-benzodiazophosphorinane 2-oxide (11) were derived from 4-thiophenoxy-1,2-diphenyldiamine (8) and 2-aminobenzylamine (10) respectively, under similar conditions. Interestingly, attempted oxidation of 5 to the corresponding sulfone 7 by H2O2 (3011) in acetic acid yielded only sulfoxide 6 12,10-dichloro-6-bis(2-chloroethyl)amino-4,8-dinitrodibenzo[d,g][1,3,6,2]dioxathiaphosphocin 6-oxide}. In an alternative approach, oxidation of 5,5'-dichloro-3,3'-dinitro-2,2'-dihydroxydiphenyl sulfide (3) with H2O2 (30%) in acetic acid formed the corresponding sulfone 4. However attempted cyclization of 4 with 1, in the presence of triethylamine, to give the sulfone expected from 5 was unsuccessful. NMR analysis of 6 suggests the presence of two conformers in solution.

  DOI：

  10.1080/10426500210247