4-Pyren-1-yl-butyric acid (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(2-diazo-acetoxy)-3-formyl-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl ester | 213546-46-4

• 分子结构分类: 有机化合物
• 英文名称: 4-Pyren-1-yl-butyric acid (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(2-diazo-acetoxy)-3-formyl-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl ester
• CAS: 213546-46-4
• 化学式: C₄₂H₄₀N₂O₈
• 分子量: 700.788
• InChiKey: UNSPGXFLMCXHBR-CSJYKKTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  52.0
• 可旋转键数：
  8.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  163.6
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-Pyren-1-yl-butyric acid (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(2-diazo-acetoxy)-3-formyl-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl ester 在 sodium tetrahydroborate 作用下， 以65%的产率得到phorbol 12-(4-pyrenebutyrate) 13-diazoacetate
  参考文献：
  名称：

  Photoaffinity labeling of PKC with a phorbol derivative: Importance of the 13-acyl group in phorbol ester-PKC interaction

  摘要：

  We report the design and synthesis of a novel photoaffinity ligand, phorbol 12-(1-pyrenebutyrate) 13-diazoacetate (PPDA, 6). This photolabile phorbol derivative labeled with tritium was used for photocrosslinking experiments with a sample of PKC partially purified from rat brain, and specific binding of 6 to PKC was observed.

  DOI：

  10.1016/0040-4039(95)01864-e
• 作为产物：
  描述：

  phorbol 20-trityl 在 4-二甲氨基吡啶 、 manganese(IV) oxide 、 异戊醇 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 9.5h， 生成 4-Pyren-1-yl-butyric acid (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(2-diazo-acetoxy)-3-formyl-4a,7b-dihydroxy-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl ester
  参考文献：
  名称：

  Photoaffinity labeling of PKC isozymes by phorbol ester derivatives

  摘要：

  Photoaffinity probes PPDA and PPTD, which have diazoacetyl and trifluorodiazopropionyl group at C-13 position in phorbol, respectively, were synthesized. Photoaffinity labeling of protein kinase C isozymes by both the probes resulted in specific cross-linking. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00068-6