1-(3-甲基丁基)吡咯烷-3-酮 | 919120-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(3-甲基丁基)吡咯烷-3-酮
• 英文名称: 1-isopentyl-3-pyrrolidone
• 英文别名: 1-(3-Methylbutyl)pyrrolidin-3-one
• CAS: 919120-46-0
• 化学式: C₉H₁₇NO
• 分子量: 155.24
• InChiKey: TXWSZLBUADVTGN-UHFFFAOYSA-N

物化性质

• 沸点：
  224.8±23.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-甲基丁基)吡咯烷-3-酮 、 5-氨基异喹啉 在 titanium(IV) isopropylate 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以29%的产率得到N-(1-isopentyl-3-pyrrolidyl)-N-(5-isoquinolyl)amine
  参考文献：
  名称：

  Design and synthesis of rho kinase inhibitors (III)

  摘要：

  The structure-activity relationship of Rho kinase inhibitors bearing an isoquinoline scaffold was studied. N-(1-Benzyl-3-pyrrolidyl)-N-(5-isoquinolyl)amine analogues were optimized with respect to their inhibitory potencies for the enzyme and for chemotaxis. The potent analogues were further evaluated by an ex vivo test in which the selected compounds were orally administered to rats, and the Rho kinase inhibitory potency observed in the rat serum was evaluated 3 h after the administration. Compound 23g showed a high level of Rho kinase inhibitory activity in the rat serum and was stable in an in vitro metabolic test using a microsomal cytochrome preparation. The (R)-isomer of 23g displayed a higher level of inhibitory potency than the (S)-isomer in a cell-free kinase assay and in the cell migration assay (IC50ENZ = 25 nM and IC50MCP = 1 mu M). The (R)-isomer successfully inhibited the phosphorylation of MBS (myosin-binding subunit) in cells. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.10.028
• 作为产物：
  描述：

  1-氯-3-甲基丁烷 在 trioxide-trimethylamine 、 potassium carbonate 、 三乙胺 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 36.0h， 生成 1-(3-甲基丁基)吡咯烷-3-酮
  参考文献：
  名称：

  Design and synthesis of rho kinase inhibitors (III)

  摘要：

  The structure-activity relationship of Rho kinase inhibitors bearing an isoquinoline scaffold was studied. N-(1-Benzyl-3-pyrrolidyl)-N-(5-isoquinolyl)amine analogues were optimized with respect to their inhibitory potencies for the enzyme and for chemotaxis. The potent analogues were further evaluated by an ex vivo test in which the selected compounds were orally administered to rats, and the Rho kinase inhibitory potency observed in the rat serum was evaluated 3 h after the administration. Compound 23g showed a high level of Rho kinase inhibitory activity in the rat serum and was stable in an in vitro metabolic test using a microsomal cytochrome preparation. The (R)-isomer of 23g displayed a higher level of inhibitory potency than the (S)-isomer in a cell-free kinase assay and in the cell migration assay (IC50ENZ = 25 nM and IC50MCP = 1 mu M). The (R)-isomer successfully inhibited the phosphorylation of MBS (myosin-binding subunit) in cells. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.10.028