ethyl 3-(cyclobutylthio)-5,5-diethoxypent-2-enoate | 1152510-49-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-(cyclobutylthio)-5,5-diethoxypent-2-enoate
• CAS: 1152510-49-0
• 化学式: C₁₅H₂₆O₄S
• 分子量: 302.435
• InChiKey: MFLWNYLTYBRUPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  20.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(cyclobutylthio)-5,5-diethoxypent-2-enoate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到ethyl 3-(cyclobutylsulfonyl)-5,5-diethoxypent-2-enoate
  参考文献：
  名称：

  Novel and efficient synthesis of 4-sulfonyl-2-pyridones

  摘要：

  Heterocyclic 4-sulfonyl-2-pyridones represent useful scaffolds for drug discovery and are also versatile synthetic building blocks. Herein we describe a novel and efficient synthesis of this heterocyclic ring system utilizing an acid mediated cyclo-condensation reaction. This synthetic method affords convenient access to structurally diverse N-substituted 4-sulfonyl-2-pyridones in moderate to good yields. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.120
• 作为产物：
  描述：

  ethyl 3-(diethoxyphosphoryloxy)-5,5-diethoxypent-2-enoate 、 methylcyclobutane 在 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 ethyl 3-(cyclobutylthio)-5,5-diethoxypent-2-enoate
  参考文献：
  名称：

  Pyridones as glucokinase activators: Identification of a unique metabolic liability of the 4-sulfonyl-2-pyridone heterocycle

  摘要：

  A promising area of novel anti-diabetic therapy involves identification of small molecule activators of the glucokinase enzyme to reduce blood glucose and normalize glucose stimulated insulin secretion. Herein, we report the identification and optimization of a series of 4-sulfonyl-2-pyridone activators. The activators were evaluated for in vitro biochemical activation and pharmacokinetic properties. As part of these efforts, a unique metabolic liability of the 4-sulfonyl-2-pyridone ring system was identified wherein this heterocycle readily undergoes conjugation with glutathione under non-enzymatic conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.107