(3a'S,7a'S)-7a'-methyl-3',3a',4',6',7',7a'-hexahydrospiro-[[1,3]dioxolane-2,5'-inden]-1'-yltrifluoromethanesulfonate | 1366053-21-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (3a'S,7a'S)-7a'-methyl-3',3a',4',6',7',7a'-hexahydrospiro-[[1,3]dioxolane-2,5'-inden]-1'-yltrifluoromethanesulfonate
• 英文别名: (3a'S,7a'S)-7a'-methyl-3',3a',4',6',7',7a'-hexahydrospiro[[1,3]dioxolane-2,5'-indene]-1'-yltrifluoromethanesulfonate；[(3'aS,7'aS)-7'a-methylspiro[1,3-dioxolane-2,5'-3a,4,6,7-tetrahydro-3H-indene]-1'-yl] trifluoromethanesulfonate
• CAS: 1366053-21-5
• 化学式: C₁₃H₁₇F₃O₅S
• 分子量: 342.336
• InChiKey: DGYYLWYWEXZUHE-ONGXEEELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3a'S,7a'S)-7a'-methyl-3',3a',4',6',7',7a'-hexahydrospiro-[[1,3]dioxolane-2,5'-inden]-1'-yltrifluoromethanesulfonate 在 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四(三苯基膦)钯 、 5% Pd/C 、 溴甲基三苯基溴化磷 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 caesium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 25.5h， 生成 4-{(Z)-[(1S,3aS,7aS)-1-(isoquinolin-7-yl)-7a-methyltetrahydro-1H-inden-5(6H,7H,7aH)-ylidene]methyl}-N,N-dimethylcyclohex-3-enamine
  参考文献：
  名称：

  Creation of Readily Accessible and Orally Active Analogue of Cortistatin A

  摘要：

  Syntheses of structurally simplified analogues of cortistatin A (1), a novel antiangiogenic steroidal alkaloid from Indonesian marine sponge, and their biological activities were investigated. The analogues were designed by considering the 3-D structure of 1. Compound 30, in which the isoquinoline moiety was appended to the planar tetracyclic core structure, showed potent antiproliferative activity against human umbilical vein endothelial cells (HUVECs) together with high selectivity and also showed in vivo antiangiogenic activity and significant antitumor effect by oral administration.

  DOI：

  10.1021/ml300143d
• 作为产物：
  描述：

  (S)-(+)-2,3,7,7A-四氢-7A-甲基-1H-茚-1,5(6H)-二酮 在 六甲基磷酰三胺 、 草酸 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 11.83h， 生成 (3a'S,7a'S)-7a'-methyl-3',3a',4',6',7',7a'-hexahydrospiro-[[1,3]dioxolane-2,5'-inden]-1'-yltrifluoromethanesulfonate
  参考文献：
  名称：

  Creation of Readily Accessible and Orally Active Analogue of Cortistatin A

  摘要：

  Syntheses of structurally simplified analogues of cortistatin A (1), a novel antiangiogenic steroidal alkaloid from Indonesian marine sponge, and their biological activities were investigated. The analogues were designed by considering the 3-D structure of 1. Compound 30, in which the isoquinoline moiety was appended to the planar tetracyclic core structure, showed potent antiproliferative activity against human umbilical vein endothelial cells (HUVECs) together with high selectivity and also showed in vivo antiangiogenic activity and significant antitumor effect by oral administration.

  DOI：

  10.1021/ml300143d

文献信息

• NOVEL CORTISTATIN A ANALOG AND USE THEREOF
  申请人：Osaka University

  公开号：EP2617720B1

  公开（公告）日：2016-03-30
• US8791263B2
  申请人：——

  公开号：US8791263B2

  公开（公告）日：2014-07-29