5,13-bis(bromomethyl)-21-methyl-8,16,24-tri(propan-2-yl)-2,10,18-trioxatetracyclo[18.4.0.04,9.012,17]tetracosa-1(24),4,6,8,12,14,16,20,22-nonaene-3,11,19-trione | 140225-54-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5,13-bis(bromomethyl)-21-methyl-8,16,24-tri(propan-2-yl)-2,10,18-trioxatetracyclo[18.4.0.04,9.012,17]tetracosa-1(24),4,6,8,12,14,16,20,22-nonaene-3,11,19-trione
• CAS: 140225-54-3
• 化学式: C₃₃H₃₄Br₂O₆
• 分子量: 686.437
• InChiKey: MREKQHUQSNWYIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  邻麝香草酸的环三内酯 在 偶氮二异丁腈 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 丙酮 为溶剂， 以3.5%的产率得到5,13-bis(bromomethyl)-21-methyl-8,16,24-tri(propan-2-yl)-2,10,18-trioxatetracyclo[18.4.0.04,9.012,17]tetracosa-1(24),4,6,8,12,14,16,20,22-nonaene-3,11,19-trione
  参考文献：
  名称：

  Analogs of tri-o-thymotide (TOT) and tri-o-carvacrotide (TOC) by direct bromination of TOT and TOC

  摘要：

  Mono-, di-, tri-, tetra-, and pentabrominated tri-o-thymotide (TOT) analogues (3-7) and mono-, di-, tri-, and tetrabrominated tri-o-carvacrotide (TOC) analogues (9-12) were synthesized by direct bromination of TOT and TOC. Total yields of about 60% were realized from TOT or TOC. The degree of bromination of the methyl group depended upon the reaction temperature and ratio of TOT (TOC):NBS. Tribromo-TOT (5) was generated in the greatest yield using a 1:18 ratio of TOT:NBS. No bromination occurred in the isopropyl group. Structure assignments were made for all new analogues. The conformational mobility of some of these analogues as well as the effect of solvents on the proton chemical shifts were studied by NMR techniques.

  DOI：

  10.1021/jo00037a045