[(3S)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-fluoro-2,6-dioxo-piperidin-1-yl]-acetic acid 1,6-dibromonaphthalen-2-yl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(3S)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-fluoro-2,6-dioxo-piperidin-1-yl]-acetic acid 1,6-dibromonaphthalen-2-yl ester
• 英文别名: (1,6-dibromonaphthalen-2-yl) 2-[(3S)-3-(1,3-dioxoisoindol-2-yl)-3-fluoro-2,6-dioxopiperidin-1-yl]acetate
• 化学式: C₂₅H₁₅Br₂FN₂O₆
• 分子量: 618.21
• InChiKey: CRBVOGVFBODQEH-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3'-fluorothalidomide 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 [(3S)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-fluoro-2,6-dioxo-piperidin-1-yl]-acetic acid 1,6-dibromonaphthalen-2-yl ester
  参考文献：
  名称：

  (R)- and (S)-3-Fluorothalidomides:  Isosteric Analogues of Thalidomide

  摘要：

  3-Fluorothalidomide, a nonracemizable isosteric analogue of thalidomide, was successfully prepared by perchloryl fluoride fluorination of a 3-phthalimidopiperidin-2-one derivative followed by RuO2 oxidation, In the preliminary biological evaluation of (R)- and (S)-enantiomers, it was shown that the (S)-isomer was found to be more active than both the (R)-isomer and the racemic thalidomide in lipopolysaccharide-induced TNF-a production enhancement produced from human peripheral blood lymphocytes cultivated in vitro.

  DOI：

  10.1021/ol9902172

文献信息

• (<i>R</i>)- and (<i>S</i>)-3-Fluorothalidomides:  Isosteric Analogues of Thalidomide
  作者：Yoshio Takeuchi、Tomoki Shiragami、Kenichi Kimura、Emiko Suzuki、Norio Shibata

  DOI：10.1021/ol9902172

  日期：1999.11.1

  3-Fluorothalidomide, a nonracemizable isosteric analogue of thalidomide, was successfully prepared by perchloryl fluoride fluorination of a 3-phthalimidopiperidin-2-one derivative followed by RuO2 oxidation, In the preliminary biological evaluation of (R)- and (S)-enantiomers, it was shown that the (S)-isomer was found to be more active than both the (R)-isomer and the racemic thalidomide in lipopolysaccharide-induced TNF-a production enhancement produced from human peripheral blood lymphocytes cultivated in vitro.