10-benzoylanhydroartemisinin | 226952-29-0

• 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: 10-benzoylanhydroartemisinin
• 英文别名: phenyl-[(1R,4S,5R,8S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadec-9-en-10-yl]methanone
• CAS: 226952-29-0
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: OVCPQIRRICXJRM-XOMRGWQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯基锂 、 10-benzoylanhydroartemisinin 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 反应 2.0h， 以91%的产率得到10-(benzhydryl)anhydroartemisinin
  参考文献：
  名称：

  Antimalarial artemisinin analogs. Synthesis via chemoselective CC bond formation and preliminary biological evaluation

  摘要：

  The peroxide bond in artemisinin trioxane lactone (1) withstood exposure to lithiothiazole and to lithiobenzothiazole; nucleophilic addition of these powerful organometallic reagents to only the lactone carbonyl group was observed. Likewise, trioxane aldehyde 5 reacted with organolithium, Grignard, and phosphorus ylide nucleophiles exclusively via carbonyl addition. Also, trioxane ketone 7b reacted with phenyllithium via only carbonyl addition. These chemoselective lactone, aldehyde, and ketone carbonyl addition reactions produced a series of new, enantiomerically pure, C-10 non-acetal derivatives of natural trioxane artemisinin having high in vitro antimalarial potencies. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01170-3
• 作为产物：
  描述：

  10-formylanhydroartemisinin 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 Angstroems MS 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 10-benzoylanhydroartemisinin
  参考文献：
  名称：

  Antimalarial artemisinin analogs. Synthesis via chemoselective CC bond formation and preliminary biological evaluation

  摘要：

  The peroxide bond in artemisinin trioxane lactone (1) withstood exposure to lithiothiazole and to lithiobenzothiazole; nucleophilic addition of these powerful organometallic reagents to only the lactone carbonyl group was observed. Likewise, trioxane aldehyde 5 reacted with organolithium, Grignard, and phosphorus ylide nucleophiles exclusively via carbonyl addition. Also, trioxane ketone 7b reacted with phenyllithium via only carbonyl addition. These chemoselective lactone, aldehyde, and ketone carbonyl addition reactions produced a series of new, enantiomerically pure, C-10 non-acetal derivatives of natural trioxane artemisinin having high in vitro antimalarial potencies. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01170-3

文献信息

• Antimalarial artemisinin analogs. Synthesis via chemoselective CC bond formation and preliminary biological evaluation
  作者：Hardwin O'Dowd、Poonsakdi Ploypradith、Suji Xie、Theresa A. Shapiro、Gary H. Posner

  DOI：10.1016/s0040-4020(98)01170-3

  日期：1999.3

  The peroxide bond in artemisinin trioxane lactone (1) withstood exposure to lithiothiazole and to lithiobenzothiazole; nucleophilic addition of these powerful organometallic reagents to only the lactone carbonyl group was observed. Likewise, trioxane aldehyde 5 reacted with organolithium, Grignard, and phosphorus ylide nucleophiles exclusively via carbonyl addition. Also, trioxane ketone 7b reacted with phenyllithium via only carbonyl addition. These chemoselective lactone, aldehyde, and ketone carbonyl addition reactions produced a series of new, enantiomerically pure, C-10 non-acetal derivatives of natural trioxane artemisinin having high in vitro antimalarial potencies. (C) 1999 Elsevier Science Ltd. All rights reserved.