2,8-di-(m-bromophenyl)-5-hydroxymethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane | 1311029-72-7

• 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: 2,8-di-(m-bromophenyl)-5-hydroxymethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane
• CAS: 1311029-72-7
• 化学式: C₁₈H₁₇Br₂NO₃
• 分子量: 455.146
• InChiKey: NWMPJGUSGDEYBK-BCDXTJNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,8-di-(m-bromophenyl)-5-hydroxymethyl-1-aza-3,7-dioxabicyclo[3.3.0]octane 在 氨 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 苯 为溶剂， 生成 bis-(2,8-di-(3-bromophenyl)-1-aza-3,7-dioxabicyclo[3.3.0]octane)-5-methyldisulfide
  参考文献：
  名称：

  Synthesis and Ring-Chain-Ring Tautomerism of Bisoxazolidines, Thiazolidinyloxazolidines, and Spirothiazolidines

  摘要：

  The synthesis of fused heterocycles such as thiazolidinyl-oxazolidine 3 is described starting from Tris center dot HCl. The mercaptomethyl bisoxazolidine 8 was found to convert to the corresponding thiazolidinyloxazolidine 3 and the spiro-heterocycle 4 by a ring-chain-ring tautomerism, depending on the electronic nature of the ring substituents as well as the reaction conditions. This equilibration pathway is absent in the hydroxymethyl bisoxazolidines 2. Computational studies confirm that both kinetic and thermodynamic control features play a role in the product distribution.

  DOI：

  10.1021/jo2008498
• 作为产物：
  描述：

  三羟甲基氨基甲烷盐酸盐 、 对溴苯甲醛 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以25%的产率得到{bis-(2,8-di-(m-bromophenyl)-1-aza-3,7-dioxabicyclo[3.3.0]-octane 5-methoxy)methyl}-3-bromobenzene
  参考文献：
  名称：

  Synthesis and Ring-Chain-Ring Tautomerism of Bisoxazolidines, Thiazolidinyloxazolidines, and Spirothiazolidines

  摘要：

  The synthesis of fused heterocycles such as thiazolidinyl-oxazolidine 3 is described starting from Tris center dot HCl. The mercaptomethyl bisoxazolidine 8 was found to convert to the corresponding thiazolidinyloxazolidine 3 and the spiro-heterocycle 4 by a ring-chain-ring tautomerism, depending on the electronic nature of the ring substituents as well as the reaction conditions. This equilibration pathway is absent in the hydroxymethyl bisoxazolidines 2. Computational studies confirm that both kinetic and thermodynamic control features play a role in the product distribution.

  DOI：

  10.1021/jo2008498