(S)-4-[(E)-(R)-1-hydroxy-11-(4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacen-8-yl)undec-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (S)-4-[(E)-(R)-1-hydroxy-11-(4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacen-8-yl)undec-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-4-[(E,1R)-11-(2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)-1-hydroxyundec-2-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• 化学式: C₃₄H₅₂BF₂N₃O₄
• 分子量: 615.612
• InChiKey: MSBNMBKAJLBCGF-OQYGYJIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-十一烯酸 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 草酰氯 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成 (S)-4-[(E)-(R)-1-hydroxy-11-(4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacen-8-yl)undec-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Borondipyrromethene (BODIPY)-Labeled Sphingosine Derivatives by Cross-metathesis Reaction

  摘要：

  A new efficient and flexible synthesis of fluorescently labeled sphingosine derivatives from commercially available Garner aldehyde (8) is described. For this, appropriate alkenylated borondipyrromethene (BODIPY) dyes were synthesized and used for the first time in a cross-metathesis reaction, the key step of the approach. The labeled sphingosines with appropriate chain length were accepted as substrates by sphingosine kinases (SPHKs), yielding the corresponding phosphorylated products. One of these derivatives (11d) was identified as the first reported selective substrate for SPHK-1.

  DOI：

  10.1021/jo062347b

文献信息

• Synthesis of Borondipyrromethene (BODIPY)-Labeled Sphingosine Derivatives by Cross-metathesis Reaction
  作者：Carsten Peters、Andreas Billich、Michael Ghobrial、Klemens Högenauer、Thomas Ullrich、Peter Nussbaumer

  DOI：10.1021/jo062347b

  日期：2007.3.1

  A new efficient and flexible synthesis of fluorescently labeled sphingosine derivatives from commercially available Garner aldehyde (8) is described. For this, appropriate alkenylated borondipyrromethene (BODIPY) dyes were synthesized and used for the first time in a cross-metathesis reaction, the key step of the approach. The labeled sphingosines with appropriate chain length were accepted as substrates by sphingosine kinases (SPHKs), yielding the corresponding phosphorylated products. One of these derivatives (11d) was identified as the first reported selective substrate for SPHK-1.