(2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'-(E)-<(trimethylsilyl)methylene>cyclohexyl>ethanoic acid | 116399-94-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'-(E)-<(trimethylsilyl)methylene>cyclohexyl>ethanoic acid
• 英文别名: 2-[(1S,2Z,3S,4R)-4-methyl-3-(3-oxobutyl)-2-(trimethylsilylmethylidene)cyclohexyl]acetic acid
• CAS: 116399-94-1
• 化学式: C₁₇H₃₀O₃Si
• 分子量: 310.509
• InChiKey: UWQRFAFORTYEHY-IBCIMESASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'-(E)-<(trimethylsilyl)methylene>cyclohexyl>ethanoic acid 以39%的产率得到
  参考文献：
  名称：

  AVERY, MITCHELL A.;JENNINGS-WHITE, CLIVE;CHONG, WESLEY K. M., TETRAHEDRON. LETT., 28,(1987) N 40, 4629-4632

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5,5-trimethyl-2-<2'-(1''(R)-methyl-3''-oxocyclohex-2''-yl)ethyl>-1,3-dioxane 在 吡啶 、 正丁基锂 、 四甲基乙二胺 、 草酸 、 silica gel 、 lithium cyclohexylisopropylamide 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'-(E)-<(trimethylsilyl)methylene>cyclohexyl>ethanoic acid
  参考文献：
  名称：

  The Total synthesis of (+)-artemisinin and (+)-9-desmethyltemesinin

  摘要：

  DOI：

  10.1016/s0040-4039(00)96582-1

文献信息

• AVERY, MITCHELL A.;JENNINGS-WHITE, CLIVE;CHONG, WESLEY K. M., TETRAHEDRON. LETT., 28,(1987) N 40, 4629-4632
  作者：AVERY, MITCHELL A.、JENNINGS-WHITE, CLIVE、CHONG, WESLEY K. M.

  DOI：——

  日期：——
• Structure−Activity Relationships of the Antimalarial Agent Artemisinin. 4. Effect of Substitution at C-3
  作者：Mitchell A. Avery、Sanjiv Mehrotra、Jason D. Bonk、Jeffrey A. Vroman、D. Keith Goins、Robert Miller

  DOI：10.1021/jm960200e

  日期：1996.1.1

  Novel antimalarial artemisinin analogs, 3-alkylartemisinins as well as 3-(arylalkyl)- and 3-(carboxyalkyl)artemisinins, were prepared via the synthetic intermediate 2. Formation of the N,N-dimethylhydrazones 5 and 24 and then regio- and chemoselective deprotonation followed by alkylation provided initially alkylated hydrazones that upon chromatography gave ketones 6-13 and 25-30. Direct ozonolysis of the ketones followed by in situ acidification lead directly to the formation of title compounds 14-21 and 31-36. The analogs were tested in vitro against W-2 and D-6 strains of Plasmodium falciparum and found to be in some cases much more active than the natural product (+)-artemisinin. The results were included in structure-activity relationship (CoMFA) studies for further analog design.
• The Total synthesis of (+)-artemisinin and (+)-9-desmethyltemesinin
  作者：Mitchell A. Avery、Clive Jennings-White、Wesley K.M. Chong

  DOI：10.1016/s0040-4039(00)96582-1

  日期：1987.1