(1R,3S,6R,8S,11S,13R,15Z,18S,20R,22S,24R,27R,29S,30R)-29-methyl-8,24-diphenyl-2,7,9,12,19,23,25,28-octaoxahexacyclo[16.13.0.03,13.06,11.020,29.022,27]hentriaconta-4,15-dien-30-ol | 1161397-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1R,3S,6R,8S,11S,13R,15Z,18S,20R,22S,24R,27R,29S,30R)-29-methyl-8,24-diphenyl-2,7,9,12,19,23,25,28-octaoxahexacyclo[16.13.0.03,13.06,11.020,29.022,27]hentriaconta-4,15-dien-30-ol
• CAS: 1161397-55-2
• 化学式: C₃₆H₄₂O₉
• 分子量: 618.724
• InChiKey: MKURKWBXZUQMOR-MWIWJDDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  45
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1R,3S,6R,8S,11S,13R,15Z,18S,20R,22S,24R,27R,29S,30R)-29-methyl-8,24-diphenyl-2,7,9,12,19,23,25,28-octaoxahexacyclo[16.13.0.03,13.06,11.020,29.022,27]hentriaconta-4,15-dien-30-ol 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以63%的产率得到(1S,3S,5R,7R,9S,12S,14R,17S,19R,21R,22S,24R,27R,29S,31R)-22-methyl-12,27-diphenyl-4,8,11,13,18,23,26,28,32-nonaoxaheptacyclo[17.13.0.03,5.07,17.09,14.022,31.024,29]dotriacont-15-en-21-ol
  参考文献：
  名称：

  Design and Synthesis of a Conformationally Restricted Analogue of the EFGH-Ring System of Ciguatoxin

  摘要：

  The fused-hexahydrooxonine (F-ring) of ciguatoxin (CTX), as well as its EFGH-ring fragment, undergoes a slow conformational change between two conformers in solution. In this paper, we designed and synthesized a conformationally restricted analogue of the EFGH-ring system of ciguatoxin. Chemo- and stereoselective epoxidation of the F-ring successfully impeded the dynamic behavior without affecting the overall three-dimensional shape of the molecule.

  DOI：

  10.3987/com-08-s(d)7
• 作为产物：
  描述：

  苯甲醛二乙缩醛 、 在 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,3S,6R,8S,11S,13R,15Z,18S,20R,22S,24R,27R,29S,30R)-29-methyl-8,24-diphenyl-2,7,9,12,19,23,25,28-octaoxahexacyclo[16.13.0.03,13.06,11.020,29.022,27]hentriaconta-4,15-dien-30-ol
  参考文献：
  名称：

  Design and Synthesis of a Conformationally Restricted Analogue of the EFGH-Ring System of Ciguatoxin

  摘要：

  The fused-hexahydrooxonine (F-ring) of ciguatoxin (CTX), as well as its EFGH-ring fragment, undergoes a slow conformational change between two conformers in solution. In this paper, we designed and synthesized a conformationally restricted analogue of the EFGH-ring system of ciguatoxin. Chemo- and stereoselective epoxidation of the F-ring successfully impeded the dynamic behavior without affecting the overall three-dimensional shape of the molecule.

  DOI：

  10.3987/com-08-s(d)7

文献信息

• Design and Synthesis of a Conformationally Restricted Analogue of the EFGH-Ring System of Ciguatoxin
  作者：Masayuki Inoue、Masahiro Hirama、Nayoung Lee

  DOI：10.3987/com-08-s(d)7

  日期：——

  The fused-hexahydrooxonine (F-ring) of ciguatoxin (CTX), as well as its EFGH-ring fragment, undergoes a slow conformational change between two conformers in solution. In this paper, we designed and synthesized a conformationally restricted analogue of the EFGH-ring system of ciguatoxin. Chemo- and stereoselective epoxidation of the F-ring successfully impeded the dynamic behavior without affecting the overall three-dimensional shape of the molecule.