3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-one | 471294-66-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-one
• CAS: 471294-66-3
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: OSYVSONSKGGOKU-UHFFFAOYSA-N

物化性质

• 沸点：
  481.2±45.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 3-(4-Methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-ol
  参考文献：
  名称：

  Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues

  摘要：

  A series of 2-(3,4,5-trimethoxyphenyl)-3-arylcyclopent-2-ene-1-ones (8a-8e) and their related analogues, including pentenone 9a, pentenol 10a, pentene 12a, and furane 15, were synthesized and evaluated for cytotoxicity against murine and human tumor cell lines. Compounds 8a-c, 8e and 9a showed strong cytotoxicity with IC50 values in the range of 8-34 ng/mL. Compound 8e exhibited significant anti-tumor activity in BDF1 mice bearing Lewis lung carcinoma cells with an inhibition ratio of 59%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00321-9
• 作为产物：
  描述：

  3,4,5-trimethoxyphenylacetyl chloride 在 吡啶 、 TEA 、 硫酸 、 溶剂黄146 、 magnesium bromide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.5h， 生成 3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-one
  参考文献：
  名称：

  Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues

  摘要：

  A series of 2-(3,4,5-trimethoxyphenyl)-3-arylcyclopent-2-ene-1-ones (8a-8e) and their related analogues, including pentenone 9a, pentenol 10a, pentene 12a, and furane 15, were synthesized and evaluated for cytotoxicity against murine and human tumor cell lines. Compounds 8a-c, 8e and 9a showed strong cytotoxicity with IC50 values in the range of 8-34 ng/mL. Compound 8e exhibited significant anti-tumor activity in BDF1 mice bearing Lewis lung carcinoma cells with an inhibition ratio of 59%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00321-9

文献信息

• Regio- and Chemoselective Bromination of 2,3-Diarylcyclopent-2-en-1-ones
  作者：Valerii Z. Shirinian、Dmitry V. Lonshakov、Vadim V. Kachala、Igor V. Zavarzin、Alexey A. Shimkin、Andrew G. Lvov、Mikhail M. Krayushkin

  DOI：10.1021/jo301474j

  日期：2012.9.21

  The bromination of 2,3-diarylcyclopent-2-en-1-ones under various conditions has been studied. It was found that depending on the brominating reagent and nature of solvent the bromine atom can be introduced at the 4- or 5-position of the ethene “bridge”, as well as into the aryl moieties. Aryl group bromination is accomplished with such reagents as molecular bromine, N-bromosuccinimide, or tetrabutylammonium

  已经研究了在各种条件下的2，3-二芳基环戊-2-烯-1-酮的溴化。已经发现，取决于溴化试剂和溶剂的性质，可以将溴原子引入乙烯“桥”的4-或5-位以及芳基部分。芳基溴化是通过诸如分子溴，N-溴琥珀酰亚胺或四丁基三溴化铵之类的试剂完成的。与溴化铜（II）在甲醇中反应可制得效率极高的5-溴环戊烯酮，而n则可制得4-溴酮。乙酸丙酯。所开发的方法对于合成在有机合成中重要的合成子的溴取代的2-环戊烯-1-酮及其紧密类似物可能非常有用，并用于制备各种有用的物质。
• Unusual, selective, reductive, deoxygenation of cyclopentenone alcohols
  作者：Suhas R. Bavikar、Trupti P. Lasonkar、Subhash P. Chavan、Hanumant B. Borate

  DOI：10.1016/j.tetlet.2014.07.122

  日期：2014.9

  A selective, reductive, deoxygenation of 2-aryl-4-hydroxycyclopent-2-en-1-ones to afford 2-aryl-cyclopent-2-en-1-ones was achieved by NaBH4–CeCl3 in methanol.

  通过在甲醇中的NaBH 4 -CeCl 3选择性地进行2-芳基-4-羟基环戊-2-烯-1-酮的还原性脱氧反应，得到2-芳基-环戊-2-烯-1-酮。
• Synthesis and anti-tumor activity of novel combretastatins: combretocyclopentenones and related analogues
  作者：Nguyen-Hai Nam、Yong Kim、Young-Jae You、Dong-Ho Hong、Hwan-Mook Kim、Byung-Zun Ahn

  DOI：10.1016/s0960-894x(02)00321-9

  日期：2002.8

  A series of 2-(3,4,5-trimethoxyphenyl)-3-arylcyclopent-2-ene-1-ones (8a-8e) and their related analogues, including pentenone 9a, pentenol 10a, pentene 12a, and furane 15, were synthesized and evaluated for cytotoxicity against murine and human tumor cell lines. Compounds 8a-c, 8e and 9a showed strong cytotoxicity with IC50 values in the range of 8-34 ng/mL. Compound 8e exhibited significant anti-tumor activity in BDF1 mice bearing Lewis lung carcinoma cells with an inhibition ratio of 59%. (C) 2002 Elsevier Science Ltd. All rights reserved.