(Z)-oct-4-en-2-ynal | 880257-23-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-oct-4-en-2-ynal
• CAS: 880257-23-8
• 化学式: C₈H₁₀O
• 分子量: 122.167
• InChiKey: BLBPJDUSPGNSEW-PLNGDYQASA-N

物化性质

• 沸点：
  196.2±13.0 °C(Predicted)
• 密度：
  0.906±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  9.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-oct-4-en-2-ynal 在 sodium chlorite 、 potassium dihydrogenphosphate 作用下， 以 二甲基亚砜 为溶剂， 生成 oct-4-en-2-ynoyl-CoA
  参考文献：
  名称：

  Inactivation of medium-chain acyl-CoA dehydrogenase by oct-4-en-2-ynoyl-CoA

  摘要：

  Mitochondrial medium-chain acyl-CoA dehydrogenase is a key enzyme for the beta-oxidation of fatty acids, which catalyzes the FAD-dependent oxidation of a variety of acyl-CoA Substrates to the corresponding trans-2-enoyl-CoA thioesters. Oct-4-en-2-ynoyl-CoA was identified as a new irreversible inhibitor of acyl-CoA dehydrogenase, and kinetic parameters K-I and k(inact) were determined to be 11 mu M and 0.025 min(-1), respectively. Triple bond between C2 and C3 of the inhibitor was identified as the functional group responsible for enzyme inactivation, and Michael addition is proposed as the mechanism for this inactivation, which is a new pathway for inactivation of MCAD by inhibitors. The inhibitor may become a lead for further development for treating non-insulin dependent diabetes mellitus. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.106
• 作为产物：
  描述：

  2-[((Z)-Oct-4-en-2-ynyl)oxy]-tetrahydro-pyran 在 甲醇 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-oct-4-en-2-ynal
  参考文献：
  名称：

  Inactivation of medium-chain acyl-CoA dehydrogenase by oct-4-en-2-ynoyl-CoA

  摘要：

  Mitochondrial medium-chain acyl-CoA dehydrogenase is a key enzyme for the beta-oxidation of fatty acids, which catalyzes the FAD-dependent oxidation of a variety of acyl-CoA Substrates to the corresponding trans-2-enoyl-CoA thioesters. Oct-4-en-2-ynoyl-CoA was identified as a new irreversible inhibitor of acyl-CoA dehydrogenase, and kinetic parameters K-I and k(inact) were determined to be 11 mu M and 0.025 min(-1), respectively. Triple bond between C2 and C3 of the inhibitor was identified as the functional group responsible for enzyme inactivation, and Michael addition is proposed as the mechanism for this inactivation, which is a new pathway for inactivation of MCAD by inhibitors. The inhibitor may become a lead for further development for treating non-insulin dependent diabetes mellitus. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.106