2,2-dimethyl-5-<(E)-3-formyl-2-propen-2-yl>-3(2H)-furanone | 136823-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2,2-dimethyl-5-<(E)-3-formyl-2-propen-2-yl>-3(2H)-furanone
• 英文别名: (E)-3-(5,5-dimethyl-4-oxofuran-2-yl)but-2-enal
• CAS: 136823-60-4
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: UTMAMHWQUBYKHM-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-<(E)-3-formyl-2-propen-2-yl>-3(2H)-furanone 、 苯基次甲基三苯基膦烷 以 二甲基亚砜 为溶剂， 反应 1.0h， 以48%的产率得到E-2,2-dimethyl-5-(1-methyl-4-phenylbutadienyl)-3(2H)-furanone
  参考文献：
  名称：

  Geiparvarin analogs. 2. Synthesis and cytostatic activity of 5-(4-arylbutadienyl)-3(2H)-furanones and of N-substituted 3-(4-oxo-2-furanyl)-2-buten-2-yl carbamates

  摘要：

  In an attempt to determine some of the structural features of geiparvarin (1) that account for its cytostatic activity in vitro, a series of geiparvarin analogues (10a-i, 1, 12, and 14-16) which contain novel modifications in the region of the olefinic double bond and of the coumarin moiety have been designed and synthesized. Among the derivatives containing a carbamate moiety, only the analogues containing a carbamate group linked to an alkyl moiety 10b-i were endowed with potent cytostatic activity, whereas the corresponding benzene derivative 10a was devoid of any antiproliferative activity. 6-Methoxygeiparvarin 101 proved equally effective as geiparvin (1), while compounds containing an additional double bond at the side chain (12 and 14-16) were invariably 5-100-fold less effective than geiparvarin. Diene derivative 15, bearing a coumarin moiety, was essentially inactive against murine (L1210, FM3A) tumor cells but exhibited good activity against human (Molt/4F, MT-4) tumor cells.

  DOI：

  10.1021/jm00115a004
• 作为产物：
  描述：

  2,2-dimethyl-5-((E)-1-methyl-3-hydroxy-1-propenyl)-3(2H)-furanone 在 吡啶 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以60%的产率得到2,2-dimethyl-5-<(E)-3-formyl-2-propen-2-yl>-3(2H)-furanone
  参考文献：
  名称：

  Geiparvarin analogs. 2. Synthesis and cytostatic activity of 5-(4-arylbutadienyl)-3(2H)-furanones and of N-substituted 3-(4-oxo-2-furanyl)-2-buten-2-yl carbamates

  摘要：

  In an attempt to determine some of the structural features of geiparvarin (1) that account for its cytostatic activity in vitro, a series of geiparvarin analogues (10a-i, 1, 12, and 14-16) which contain novel modifications in the region of the olefinic double bond and of the coumarin moiety have been designed and synthesized. Among the derivatives containing a carbamate moiety, only the analogues containing a carbamate group linked to an alkyl moiety 10b-i were endowed with potent cytostatic activity, whereas the corresponding benzene derivative 10a was devoid of any antiproliferative activity. 6-Methoxygeiparvarin 101 proved equally effective as geiparvin (1), while compounds containing an additional double bond at the side chain (12 and 14-16) were invariably 5-100-fold less effective than geiparvarin. Diene derivative 15, bearing a coumarin moiety, was essentially inactive against murine (L1210, FM3A) tumor cells but exhibited good activity against human (Molt/4F, MT-4) tumor cells.

  DOI：

  10.1021/jm00115a004