2,2-Dimethyl-propionic acid 2-benzyl-pent-4-enyl ester | 205373-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-Dimethyl-propionic acid 2-benzyl-pent-4-enyl ester
• 英文别名: 2-benzylpent-4-enyl 2,2-dimethylpropanoate
• CAS: 205373-46-2
• 化学式: C₁₇H₂₄O₂
• 分子量: 260.376
• InChiKey: YGGYVJZUZFAFKL-UHFFFAOYSA-N

物化性质

• 沸点：
  329.1±21.0 °C(Predicted)
• 密度：
  0.965±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid 2-benzyl-pent-4-enyl ester 在 N-溴代丁二酰亚胺(NBS) 、 jones' reagent 、 potassium tert-butylate 、 二异丁基氢化铝 、 氟化氢吡啶 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.5h， 生成 2-benzyl-4-fluoro-4-pentenoic acid
  参考文献：
  名称：

  A novel type of structurally simple nonpeptide inhibitors for α-chymotrypsin. Induced-fit binding of methyl 2-allyl-3-benzene-propanoate to the S2 subsite pocket

  摘要：

  Unexpectedly, methyl and benzyl esters of 2-allyl-3-benzenepropanoic acid were found to be not substrates but potent competitive inhibitors for alpha-chymotrypsin. The inhibitory property of the structurally simple nonpeptidic compounds is ascribed to their high binding affinity to the enzyme at the S-2 rather than S-1 subsite pocket. These inhibitors exist in a flexible form in solution, but as they bind to the enzyme bulky contrained conformers present in a minute concentration play an important role, forming tighter enzyme-inhibitor complexes by binding to the large hydrophobic S-2 pocket. The contrained conformers are thought to be resulted from intramolecular CH/pi interactions between a vinylic proton and the aromatic pi-electron cloud in the inhibitor molecules. These compounds constitute novel examples of the induced-fit binding inhibitor of possibly simplest structure. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10038-4
• 作为产物：
  描述：

  methyl 2-benzylpent-4-enoate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 2,2-Dimethyl-propionic acid 2-benzyl-pent-4-enyl ester
  参考文献：
  名称：

  A novel type of structurally simple nonpeptide inhibitors for α-chymotrypsin. Induced-fit binding of methyl 2-allyl-3-benzene-propanoate to the S2 subsite pocket

  摘要：

  Unexpectedly, methyl and benzyl esters of 2-allyl-3-benzenepropanoic acid were found to be not substrates but potent competitive inhibitors for alpha-chymotrypsin. The inhibitory property of the structurally simple nonpeptidic compounds is ascribed to their high binding affinity to the enzyme at the S-2 rather than S-1 subsite pocket. These inhibitors exist in a flexible form in solution, but as they bind to the enzyme bulky contrained conformers present in a minute concentration play an important role, forming tighter enzyme-inhibitor complexes by binding to the large hydrophobic S-2 pocket. The contrained conformers are thought to be resulted from intramolecular CH/pi interactions between a vinylic proton and the aromatic pi-electron cloud in the inhibitor molecules. These compounds constitute novel examples of the induced-fit binding inhibitor of possibly simplest structure. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10038-4