(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 | 1161397-57-4

分子结构分类

有机化合物 - 有机杂环化合物 - 氧杂环己烷

中文名称

——

中文别名

——

英文名称

(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

英文别名

——

(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化学式

CAS

1161397-57-4

化学式

C₃₆H₄₂O₁₀

mdl

——

分子量

634.723

InChiKey

BAFUPXIDAVCTBJ-XXVVMJCHSA-N

BEILSTEIN

——

EINECS

——

计算性质

辛醇/水分配系数(LogP)：

2.7
重原子数：

46
可旋转键数：

2
环数：

9.0
sp3杂化的碳原子比例：

0.61
拓扑面积：

107
氢给体数：

1
氢受体数：

10

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
——	(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	C₃₆H₄₂O₉	618.724

反应信息

作为产物：

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

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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.

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