allyl 2-benzoyl-3-(2-ethylphenyl)-5-oxopentanoate | 923002-42-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: allyl 2-benzoyl-3-(2-ethylphenyl)-5-oxopentanoate
• CAS: 923002-42-0
• 化学式: C₂₃H₂₄O₄
• 分子量: 364.441
• InChiKey: RVVVELJQKWOUAI-UHFFFAOYSA-N

物化性质

• 沸点：
  448.6±34.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  27.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  allyl 2-benzoyl-3-(2-ethylphenyl)-5-oxopentanoate 在 盐酸 、 水 、 溴甲酚绿 、 三乙酰氧基硼氢化钠 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 rac-3-allyl [(2S,4R)-4-(2-ethylphenyl)-2-phenyl-1-N-(3-pyridylmethyl)-piperidin-(3S)-3-yl]carboxylate
  参考文献：
  名称：

  Design and synthesis of piperidine farnesyltransferase inhibitors with reduced glucuronidation potential

  摘要：

  The design and synthesis of a novel piperidine series of farnesyltransferase (FTase) inhibitors with reduced potential for metabolic glucuronidation are described. The various substitution and exchange of the phenyl group at the C-2 position of the previously described 2-(4-hydroxy)phenyl-3-nitropiperidine 1a (FTase IC50 = 5.4 nM) resulted in metabolically stable compounds with potent FTase inhibition (14a IC50 = 4.3 nM, 20a IC50 = 3.0 nM, and 50a IC50 = 16 nM). Molecular modeling studies of these compounds complexed with FTasc and farnesyl pyrophosphate are also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.11.007
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 在 4-二甲氨基吡啶 、 lithium salt of proline 作用下， 以 氯仿 为溶剂， 反应 138.0h， 生成 allyl 2-benzoyl-3-(2-ethylphenyl)-5-oxopentanoate
  参考文献：
  名称：

  Design and synthesis of piperidine farnesyltransferase inhibitors with reduced glucuronidation potential

  摘要：

  The design and synthesis of a novel piperidine series of farnesyltransferase (FTase) inhibitors with reduced potential for metabolic glucuronidation are described. The various substitution and exchange of the phenyl group at the C-2 position of the previously described 2-(4-hydroxy)phenyl-3-nitropiperidine 1a (FTase IC50 = 5.4 nM) resulted in metabolically stable compounds with potent FTase inhibition (14a IC50 = 4.3 nM, 20a IC50 = 3.0 nM, and 50a IC50 = 16 nM). Molecular modeling studies of these compounds complexed with FTasc and farnesyl pyrophosphate are also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.11.007