[(4S,6S,7R,8S)-11-amino-5-[(2R)-3-(1,3-dioxoisoindol-2-yl)-2-fluoropropanoyl]-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate | 1205648-14-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: [(4S,6S,7R,8S)-11-amino-5-[(2R)-3-(1,3-dioxoisoindol-2-yl)-2-fluoropropanoyl]-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
• CAS: 1205648-14-1
• 化学式: C₂₆H₂₄FN₅O₈
• 分子量: 553.504
• InChiKey: NRTGHIAVZFGBHJ-FFQDXNTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  182
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  1,3-二氢-1,3-二氧代-2H-异吲哚-2-丙酰氯 、 丝裂霉素 C 在 bis-triphenylphosphine-palladium(II) chloride 、 benzoylquinidine 、 N-氟代双苯磺酰胺 、 N,N-二异丙基乙胺 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以58.7%的产率得到[(4S,6S,7R,8S)-11-amino-5-[(2R)-3-(1,3-dioxoisoindol-2-yl)-2-fluoropropanoyl]-7-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
  参考文献：
  名称：

  Combining Asymmetric Catalysis with Natural Product Functionalization through Enantioselective α-Fluorination

  摘要：

  An examination into the derivatization of various natural products using newly developed alpha-fluorination methodology is disclosed. An activated ketene enolate, generated from in acid chloride, is allowed to react with an electrophilic fluorine source (NFSi). Quenching the reaction with a nucleophilic natural product produces biologically relevant alpha-fluorinated carbonyl derivatives of select chemotherapeutics, antibiotics, and other pharmaceuticals.

  DOI：

  10.1021/jo9024072

文献信息

• Combining Asymmetric Catalysis with Natural Product Functionalization through Enantioselective α-Fluorination
  作者：Jeremy Erb、Ethan Alden-Danforth、Nathan Kopf、Michael T. Scerba、Thomas Lectka

  DOI：10.1021/jo9024072

  日期：2010.2.5

  An examination into the derivatization of various natural products using newly developed alpha-fluorination methodology is disclosed. An activated ketene enolate, generated from in acid chloride, is allowed to react with an electrophilic fluorine source (NFSi). Quenching the reaction with a nucleophilic natural product produces biologically relevant alpha-fluorinated carbonyl derivatives of select chemotherapeutics, antibiotics, and other pharmaceuticals.