2-methyl-2-(4'-methyl-3'-pentenyl)-7-methoxy-4-chromanone | 122587-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-methyl-2-(4'-methyl-3'-pentenyl)-7-methoxy-4-chromanone
• 英文别名: 2-methyl-2-(4-methyl-3-pentenyl)-7-methoxy-2,3-dihydro-4H-benzopyran-4-one；7-Methoxy-2-methyl-2-(4-methylpent-3-enyl)chroman-4-one；7-methoxy-2-methyl-2-(4-methylpent-3-enyl)-3H-chromen-4-one
• CAS: 122587-25-1
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: PTLCCRHMOFLHDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-2-(4'-methyl-3'-pentenyl)-7-methoxy-4-chromanone 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 (4α,7α,9α)-4,8,8-trimethyl-14-oxatetracyclo<6.5.1^4.13.0^1.9>tetradec-12-ene-2,11-dione
  参考文献：
  名称：

  一种新型的分子内1,2-芳烃-烯烃光环加成反应

  摘要：

  2-烯基-7-羟基-4-苯并二氢吡喃酮的新型分子内1,2-芳烃-烯烃光环加成反应（1）及其烷基醚（2和3）变为（4α，7α，9α）4,8,8-三甲基-14-氧杂四环（6.5.1 4,13 0.0 1,9-）十四碳-12-烯-2,11-二酮（4）进行说明。

  DOI：

  10.1016/0040-4039(93)88043-i
• 作为产物：
  描述：

  6-甲基-5-庚烯-2-酮 在 四氢吡咯 、 3 A molecular sieve 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 24.0h， 生成 2-methyl-2-(4'-methyl-3'-pentenyl)-7-methoxy-4-chromanone
  参考文献：
  名称：

  Structure-Based de Novo Design, Synthesis, and Biological Evaluation of Non-Azole Inhibitors Specific for Lanosterol 14α-Demethylase of Fungi

  摘要：

  The active site of lanosterol 14alpha-demethylase (CYP51) was investigated via MCSS functional group mapping and LUDI calculations. Several non-azole lead molecules were obtained by coupling structure-based de novo design with chemical synthesis and biological evaluation. All of the lead molecules exhibited a strong inhibitory effect on CYP51 of Candida albicans. They occupy the substrate-binding site and interfere with the binding of azole antifungal agents in a competitive manner. The mode of action of the lead molecules was validated by spectrophotomeric analysis and SAR studies. This is the first successful example reported for the inhibitor design of the cytochrome P450 superfamily using the de novo design strategy. Because the affinity of the lead molecules for CYP51 was mainly attributed to their nonbonding interaction with the apoprotein, the studies presented here afford the opportunity to develop novel antifungal agents that specifically interact with the residues in the active site and avoid the serious toxicity arising from coordination binding with the heme of mammalian P450s.

  DOI：

  10.1021/jm020362c

文献信息

• Stereo- and regioselectivity of intramolecular 1,2-arene-alkene photocycloaddition in 2-alkenyl-4-chromanones
  作者：Govind P. Kalena、Padmanava Pradhan、Asoke Banerji

  DOI：10.1016/s0040-4020(98)01134-x

  日期：1999.3

  Intramolecular 1,2-arene-alkene photocycloaddition of 2-alkenyl-4-chromanones gave complex multicyclic oxatetracyclotetradecanediones which on internal photo- and microwave induced thermal rearrangements provided a diverse array of compounds with [3.3.0]bicyclooctane carbon frame work. The stereo- and regiochemical aspects as well as desymmetrization of alkenyl chromanones due to intramolecular 1,2-arenealkene

  2-烯基-4-发色酮的分子内1,2-芳烃-烯烃光环加成反应生成复杂的多环草酸酯四环十二烷二酮，在内部光和微波诱导的热重排下，提供了具有[3.3.0]双环辛烷碳骨架的多种化合物。还讨论了由于分子内1，2-亚芳基烯烃的光环加成而引起的烯基苯并二氢呋喃酮的立体和区域化学方面以及去对称化。
• Banerji, A.; Kalena, G.P., Synthetic Communications, 1989, vol. 19, # 1, 2, p. 159 - 166
  作者：Banerji, A.、Kalena, G.P.

  DOI：——

  日期：——
• BANERJI, A.;KALENA, G. P., SYNTH. COMMUN., 19,(1989) N-2, C. 159-166
  作者：BANERJI, A.、KALENA, G. P.

  DOI：——

  日期：——
• Structure-Based de Novo Design, Synthesis, and Biological Evaluation of Non-Azole Inhibitors Specific for Lanosterol 14α-Demethylase of Fungi
  作者：Haitao Ji、Wannian Zhang、Min Zhang、Makiko Kudo、Yuri Aoyama、Yuzo Yoshida、Chunquan Sheng、Yunlong Song、Song Yang、Youjun Zhou、Jiaguo Lü、Jü Zhu

  DOI：10.1021/jm020362c

  日期：2003.2.1

  The active site of lanosterol 14alpha-demethylase (CYP51) was investigated via MCSS functional group mapping and LUDI calculations. Several non-azole lead molecules were obtained by coupling structure-based de novo design with chemical synthesis and biological evaluation. All of the lead molecules exhibited a strong inhibitory effect on CYP51 of Candida albicans. They occupy the substrate-binding site and interfere with the binding of azole antifungal agents in a competitive manner. The mode of action of the lead molecules was validated by spectrophotomeric analysis and SAR studies. This is the first successful example reported for the inhibitor design of the cytochrome P450 superfamily using the de novo design strategy. Because the affinity of the lead molecules for CYP51 was mainly attributed to their nonbonding interaction with the apoprotein, the studies presented here afford the opportunity to develop novel antifungal agents that specifically interact with the residues in the active site and avoid the serious toxicity arising from coordination binding with the heme of mammalian P450s.
• A novel intramolecular 1,2-arene-alkene photocycloaddition
  作者：G.P. Kalena、P. Pradhan、A. Banerji

  DOI：10.1016/0040-4039(93)88043-i

  日期：1992.12

  A novel intramolecular 1,2-arene-alkene photocycloaddition of 2-alkenyl-7-hydroxy-4-chromanone(1) and its alkyl ethers (2 and 3) to (4α, 7α, 9α)4,8,8-trimethyl-14-oxatetracyclo(6.5.14,13.01,9)tetradeca-12-ene-2,11-dione (4) is described.

  2-烯基-7-羟基-4-苯并二氢吡喃酮的新型分子内1,2-芳烃-烯烃光环加成反应（1）及其烷基醚（2和3）变为（4α，7α，9α）4,8,8-三甲基-14-氧杂四环（6.5.1 4,13 0.0 1,9-）十四碳-12-烯-2,11-二酮（4）进行说明。