4-(coumarin-7-yloxy)-2-methyl-2(E)-butenal | 78957-45-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-(coumarin-7-yloxy)-2-methyl-2(E)-butenal
• 英文别名: (E)-4-(2-oxo-2H-chromen-7-yloxy)-2-methyl-2-butenal；(E)-2-methyl-4-(2-oxo-2H-1-benzopyran-7-yloxy)but-2-enal；7(3'-Formylbut-2'-enoxy)coumarin；(E)-2-methyl-4-(2-oxochromen-7-yl)oxybut-2-enal
• CAS: 78957-45-6
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: BOEYBMJEVSXRSZ-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(coumarin-7-yloxy)-2-methyl-2(E)-butenal 在 草酰氯 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 7-((E)-7-Hydroxy-3,7-dimethyl-4-oxo-oct-2-en-5-ynyloxy)-chromen-2-one
  参考文献：
  名称：

  Inoue, Y.; Ohuchi, K.; Imaizumi, S., Synthetic Communications, 1990, vol. 20, # 19, p. 3063 - 3068

  摘要：

  DOI：
• 作为产物：
  描述：

  7-[(E)-3'-methyl-4'-hydroxy-2'-butenyloxy]coumarin 在 chromium(VI) oxide 作用下， 以 丙酮 为溶剂， 以76%的产率得到4-(coumarin-7-yloxy)-2-methyl-2(E)-butenal
  参考文献：
  名称：

  Inoue, Y.; Ohuchi, K.; Imaizumi, S., Synthetic Communications, 1990, vol. 20, # 19, p. 3063 - 3068

  摘要：

  DOI：

文献信息

• Regiocontrolled Formation of 4,5-Dihydro-3(2<i>H</i>)-furanones from 2-Butyne-1,4-diol Derivatives. Synthesis of Bullatenone and Geiparvarin
  作者：Hiroyuki Saimoto、Tamejiro Hiyama、Hitosi Nozaki

  DOI：10.1246/bcsj.56.3078

  日期：1983.10

  Two new methods for selective hydration of 1,1,4-trisubstituted 2-butyne-1,4-diols (1) to give 4,5-dihydro-3(2H)-furanone derivatives are reported. The first involves selective monoacetylation of the less hindered hydroxyl group of 1 followed by Ag(I)-catalyzed rearrangement and cyclization to give 3-acetoxy-2,2,5-trisubstituted 2,5-dihydrofurans (2). Final hydrolysis yielded 2,2,5-trisubstituted 4

  报告了两种新方法，用于选择性水合 1,1,4-三取代的 2-丁炔-1,4-二醇 (1) 以生成 4,5-二氢-3(2H)-呋喃酮衍生物。第一个涉及 1 的受阻较小的羟基的选择性单乙酰化，然后是 Ag(I) 催化的重排和环化，得到 3-乙酰氧基-2,2,5-三取代的 2,5-二氢呋喃 (2)。最后水解产生2,2,5-三取代的4,5-二氢-3(2H)-呋喃酮。用2,3-二氯-5,6-二氰基-1,4-苯醌氧化烯醇乙酸酯2，得到3(2H)-呋喃酮。新方法用于从相应的 2-丁炔-1,4-二醇衍生物合成天然存在的 3(2H)-呋喃酮，如布拉藤酮和 Geiparvarin。第二种方法涉及相反区域异构体 2,5,5-三取代的 4,5-二氢-3(2H)-呋喃酮的合成，
• Regiocontrolled hydration of 2-butyne-1,4-diol derivatives to give 4,5-dihydro-3(2H)-furanones. Practical synthesis of bullatenone and geiparvarin
  作者：Hiroyuki Saimoto、Tamejiro Hiyama、Hitosi Nozaki

  DOI：10.1021/ja00406a066

  日期：1981.8
• Geiparvarin Analogues: Synthesis and Anticancer Evaluation ofα-Methylidene-γ-butyrolactone-Bearing Coumarins
  作者：Yeh-Long Chen、Tai-Chi Wang、Cherng-Chyi Tzeng、Nein-Chen Chang

  DOI：10.1002/(sici)1522-2675(19990210)82:2<191::aid-hlca191>3.0.co;2-p

  日期：1999.2.10

  To determine some of the structural features of geiparvarin that account for its cytostatic activity in vitro, certain geiparvarin analogues modified in the furan-3(2H)-one moiety and the alkenyloxy substituent were synthesized and tested against the growth of 60 human cancer cell lines derived from nine cancer-cell types. These compounds demonstrated a strong growth-inhibitory activity against leukemia cell lines but were relatively inactive against non-small-cell lung cancers and CNS cancers. Comparison of the mean log GI, values of gamma-[(E)-1-methylprop-1-enyl]-alpha-methylidene-gamma-butyrolactones 7-9 revealed that 7-[(E)-3-(2,3,4,5-tetrahydro-4-methylidene-5-oxofuran-2-yl)but-2-enyloxy]-2H-1-benzopyran-2-one (8: - 5.47) was more active than its 6-substituted counterpart 7 (- 5.21) and its 3-chloro-4-methyl derivative 9 (- 5.31) and had a potency similar to that of geiparvarin (log GI(50) = - 5.41). These results indicated that the furan-3(2H)-one moiety of geiparvarin could be replaced by an alpha-methylidene-gamma-butyrolactone unit without losing the anticancer potency, (:nd that the best substitution site at the coumarin moiety was C(7). The alkenyloxy substituent of 8 was also replaced by a methoxy substituent. Among these alpha-methylidene-gamma-butyrolactones, 7-[(2,3,4,5-tetrahydro-4-methylidene-5-oxo-2-phenyliuran-2-yl)methoxy]-2H-1-benzopyran-2-one (1l) was the most potent with a mean log GI(50) value of - 5.83 and a range value of 132(10(212)).
• INOUE, Y.;OHUCHI, K.;IMAIZUMI, S.;HAGIWARA, H.;UDA, H., SYNTH. COMMUN., 20,(1990) N9, C. 3063-3068
  作者：INOUE, Y.、OHUCHI, K.、IMAIZUMI, S.、HAGIWARA, H.、UDA, H.

  DOI：——

  日期：——