tri-o-carvacrotide | 2281-45-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tri-o-carvacrotide
• 英文别名: Tricarvocrotide；8,16,24-trimethyl-5,13,21-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: 2281-45-0
• 化学式: C₃₃H₃₆O₆
• 分子量: 528.645
• InChiKey: KXGZHYZDRUARHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  39
• 可旋转键数：
  3
• 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

• 作为反应物：
  描述：

  tri-o-carvacrotide 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22%的产率得到8,16,24-tris(bromomethyl)-5,13,21-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
• 作为产物：
  描述：

  2-羟基-6-异丙基-3-甲基苯甲酸 在 三氯氧磷 作用下， 反应 2.0h， 以65%的产率得到tri-o-carvacrotide
  参考文献：
  名称：

  Improved preparation of the clathrate host compound tri-o-thymotide and related trisalicylide derivatives

  摘要：

  In order to improve the relatively low yield (ca. 35%) previously observed in the synthesis of tri-o-thymotide (TOT, 1) from o-thymotic acid (2), the cyclodehydration was studied using a variety of conditions. The low yield is due to the formation of di-o-thymotide (DOT, 3), previously reported, and at least three other products (4-6), which apparently result from the acid-catalyzed decarboxylation of 2 and subsequent condensation with thymol (7). Using pyridine as a solvent, side-product formation is inhibited. Under appropriate conditions, namely, neat POCl3 at 50-degrees-C, the yield of 1 is 93%. Other salicylic acid derivatives also give high yields of the corresponding ''trimers'' under these conditions, thus providing a general, improved preparation of a family of potential clathrate host substances.

  DOI：

  10.1021/jo00014a037

文献信息

• Baker et al., Journal of the Chemical Society, 1954, p. 2042,2046
  作者：Baker et al.

  DOI：——

  日期：——
• GNAIM, JALLAL M.;GREEN, BERNARD S.;ARAD-YELLIN, RINA;KEEHN, PHILIP M., J. ORG. CHEM., 56,(1991) N4, C. 4525-4529
  作者：GNAIM, JALLAL M.、GREEN, BERNARD S.、ARAD-YELLIN, RINA、KEEHN, PHILIP M.

  DOI：——

  日期：——
• Improved preparation of the clathrate host compound tri-o-thymotide and related trisalicylide derivatives
  作者：Jallal M. Gnaim、Bernard S. Green、Rina Arad-Yellin、Philip M. Keehn

  DOI：10.1021/jo00014a037

  日期：1991.7

  In order to improve the relatively low yield (ca. 35%) previously observed in the synthesis of tri-o-thymotide (TOT, 1) from o-thymotic acid (2), the cyclodehydration was studied using a variety of conditions. The low yield is due to the formation of di-o-thymotide (DOT, 3), previously reported, and at least three other products (4-6), which apparently result from the acid-catalyzed decarboxylation of 2 and subsequent condensation with thymol (7). Using pyridine as a solvent, side-product formation is inhibited. Under appropriate conditions, namely, neat POCl3 at 50-degrees-C, the yield of 1 is 93%. Other salicylic acid derivatives also give high yields of the corresponding ''trimers'' under these conditions, thus providing a general, improved preparation of a family of potential clathrate host substances.
• Analogs of tri-o-thymotide (TOT) and tri-o-carvacrotide (TOC) by direct bromination of TOT and TOC
  作者：Lulu Xu、Philip M. Keehn、Jallal M. Gnaim、Bernard S. Green

  DOI：10.1021/jo00037a045

  日期：1992.5

  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.