10β-fluoro-10-deoxoartemisinin | 204503-62-8

• 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: 10β-fluoro-10-deoxoartemisinin
• 英文别名: 10β-fluoro-10-deoxydihydroartemisinin；(3R,5aS,6R,8aS,9R,10R,12S,12aR)-10-fluoro-3,6,9-trimethyldecahydro-12H-3,12-epoxypyrano[4,3-j][1,2] benzodioxane；(1R,4S,5R,8S,9R,10R,12S,13R)-10-fluoro-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
• CAS: 204503-62-8
• 化学式: C₁₅H₂₃FO₄
• 分子量: 286.344
• InChiKey: VCAQSWKSXGITDC-ISOSDAIHSA-N

物化性质

• 沸点：
  330.5±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  10β-fluoro-10-deoxoartemisinin 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  双-(10-去氧双氢青蒿素)-间苯三酚衍生物的制备及应用

  摘要：

  本发明公开了一种双‑(10‑去氧双氢青蒿素)‑间苯三酚衍生物，其结构式如下所示，

  公开号：

  CN114213435B
• 作为产物：
  描述：

  双氢青蒿素 在 potassium fluoride 、 1,3-双(2,6-二异丙苯基)-2,2-二氟-2,3-二氢-1H-咪唑 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以79%的产率得到10β-fluoro-10-deoxoartemisinin
  参考文献：
  名称：

  Late-Stage Deoxyfluorination of Alcohols with PhenoFluor

  摘要：

  An operationally simple protocol for the selective deoxyfluorination of structurally complex alcohols is presented. Several fluorinated derivatives of natural products and pharmaceuticals have been prepared to showcase the potential of the method for late-stage diversification and its functional group compatibility. A series of simple guidelines for predicting the selectivity in substrates with multiple alcohols is given.

  DOI：

  10.1021/ja3125405

文献信息

• Direct conversion of pyranose anomeric OH→F→R in the artemisinin family of antimalarial trioxanes
  作者：Soon Hyung Woo、Michael H. Parker、Poonsakdi Ploypradith、John Northrop、Gary H. Posner

  DOI：10.1016/s0040-4039(98)00132-4

  日期：1998.3

  Eleven examples form the basis of a short and effective synthetic method for replacement of an anomeric fluorine atom by saturated, unsaturated, aryl and heteroaryl carbon nucleophiles to prepare alpha- or beta-oriented C-10-R derivatives of the trioxane 10-deoxoartemisinin. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Antimalarial, Antiproliferative, and Antitumor Activities of Artemisinin-Derived, Chemically Robust, Trioxane Dimers
  作者：Gary H. Posner、Poonsakdi Ploypradith、Michael H. Parker、Hardwin O'Dowd、Soon-Hyung Woo、John Northrop、Mikhail Krasavin、Patrick Dolan、Thomas W. Kensler、Suji Xie、Theresa A. Shapiro

  DOI：10.1021/jm990363d

  日期：1999.10.1

  Nine C-10 non-acetal derivatives of the natural trioxane artemisinin (1) were prepared as dimers using some novel chemistry. As designed, each dimer was stable chemically. C-10 Olefinic dimers 7 and C-10 saturated dimers 8-13 all showed good to excellent antimalarial and antiproliferative activities in vitro. Dimers 8, 10, and 12 were especially potent and selective at inhibiting growth of some human cancer cell lines in the NCI in vitro 60-cell line assay.
• TW2023/9044
  申请人：——

  公开号：——

  公开（公告）日：——