(E)-4-Methyl-3-oxo-hept-4-enenitrile | 762288-37-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-4-Methyl-3-oxo-hept-4-enenitrile
• CAS: 762288-37-9
• 化学式: C₈H₁₁NO
• 分子量: 137.181
• InChiKey: LFZXPZYTOJZPJR-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-4-Methyl-3-oxo-hept-4-enenitrile 在 氟化铵 、 ammonium hydroxide 、 正丁基锂 、 pyridine-SO3 complex 、 三苯甲基氢过氧化物 、 silica gel 、 溶剂黄146 、 ethylenediamine Tetraacetic Acid 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (1R,5R)-4-hydroxy-4-methyl-1-(methylpent-2-enoyl)-6-oxa-3-azabicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Structure–activity relationships of epolactaene derivatives: structural requirements for inhibition of Hsp60 chaperone activity

  摘要：

  Epolactaene is a microbial metabolite isolated from the fungal strain Penicillium sp. It arrests the cell cycle at the G(0)/G(1), phase and induces the outgrowth of neurites in human neuroblastoma SH-SY5Y cells. In this communication, we report the structure-activity relationships (SARs) of new epolactaene derivatives, including those lacking the epoxylactam moiety and having various side chains. These derivatives were evaluated for their ability to inhibit the growth of human cancer cell lines. They were also analyzed for their ability to affect human heat shock protein 60 (Hsp60), which we have already identified as a protein that binds to epolactaene. We also identified the important structural framework of epolactaene/ETB (epolactaene tertiary butyl ester) for not only binding to Hsp60 but also inhibiting Hsp60 chaperone activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.054
• 作为产物：
  描述：

  丙醛 、 (3-Cyano-1-methyl-2-oxo-propyl)-phosphonic acid diethyl ester 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 生成 (E)-4-Methyl-3-oxo-hept-4-enenitrile
  参考文献：
  名称：

  Structure–activity relationships of epolactaene derivatives: structural requirements for inhibition of Hsp60 chaperone activity

  摘要：

  Epolactaene is a microbial metabolite isolated from the fungal strain Penicillium sp. It arrests the cell cycle at the G(0)/G(1), phase and induces the outgrowth of neurites in human neuroblastoma SH-SY5Y cells. In this communication, we report the structure-activity relationships (SARs) of new epolactaene derivatives, including those lacking the epoxylactam moiety and having various side chains. These derivatives were evaluated for their ability to inhibit the growth of human cancer cell lines. They were also analyzed for their ability to affect human heat shock protein 60 (Hsp60), which we have already identified as a protein that binds to epolactaene. We also identified the important structural framework of epolactaene/ETB (epolactaene tertiary butyl ester) for not only binding to Hsp60 but also inhibiting Hsp60 chaperone activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.054