(S)-4-(1,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid | 116162-02-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (S)-4-(1,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid
• 英文别名: (S)-fridamycin E；(3S)-4-(1,5-dihydroxy-9,10-dioxoanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid
• CAS: 116162-02-8
• 化学式: C₁₉H₁₆O₇
• 分子量: 356.332
• InChiKey: MVEDBMGRQONWSQ-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-hydroxy-5-(2'-methylprop-2'-enyloxy)-9,10-anthraquinone 在 四氧化锇 、 hydroquinidine 1 4-phthalazinediyl diether 、 sodium dithionite 、 1,4-环己二烯 、 palladium 10% on activated carbon 、 bis(tetrahydrofuran)-meso-tetra(4-chlorophenyl)porphyrinato aluminum tetracarbonyl cobaltate 、 水 、 sodium hydride 、 二正丁基氧化锡 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 、 叔丁醇 为溶剂， 90.0 ℃ 、6.21 MPa 条件下， 反应 26.0h， 生成 (S)-4-(1,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)-3-hydroxy-3-methylbutanoic acid
  参考文献：
  名称：

  De Novo Asymmetric Synthesis of Fridamycin E

  摘要：

  A de novo asymmetric synthesis of (R)- and (S)-fridamycin E has been achieved. The entirely linear route required only nine steps from commercially available starting materials (16% overall yield). Key transformations included a Claisen rearrangement, a Sharpless dihydroxylation and a cobalt-catalyzed epoxide carbonylation to give a beta-lactone intermediate. Antibacterial activities were determined for both enantiomers using two strains of E. coli, with the natural (R)-enantiomer showing significant inhibition against a Gram-(+)-like imp strain (MIC = 8 mu M).

  DOI：

  10.1021/ol203041b

文献信息

• <i>De Novo</i> Asymmetric Synthesis of Fridamycin E
  作者：Qian Chen、Michael Mulzer、Pei Shi、Penny J. Beuning、Geoffrey W. Coates、George A. O’Doherty

  DOI：10.1021/ol203041b

  日期：2011.12.16

  A de novo asymmetric synthesis of (R)- and (S)-fridamycin E has been achieved. The entirely linear route required only nine steps from commercially available starting materials (16% overall yield). Key transformations included a Claisen rearrangement, a Sharpless dihydroxylation and a cobalt-catalyzed epoxide carbonylation to give a beta-lactone intermediate. Antibacterial activities were determined for both enantiomers using two strains of E. coli, with the natural (R)-enantiomer showing significant inhibition against a Gram-(+)-like imp strain (MIC = 8 mu M).