(2E,4E)-1-(furan-2-yl)-5-(2-nitrophenyl)penta-2,4-dien-1-one | 135950-71-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E,4E)-1-(furan-2-yl)-5-(2-nitrophenyl)penta-2,4-dien-1-one
• CAS: 135950-71-9
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: GJSBDUCICHICKM-TUXQVTDXSA-N

物化性质

• 沸点：
  446.1±45.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E,4E)-1-(furan-2-yl)-5-(2-nitrophenyl)penta-2,4-dien-1-one 、 苯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以77%的产率得到(E)-3-(2-(furan-2-yl)-2-oxoethyl)-5-(2-nitrophenyl)-2-phenylpent-4-enenitrile
  参考文献：
  名称：

  苯乙腈与 1,5-diarylpenta-2,4-dien-1-ones 的区域特异性 1,4-Michael 加成

  摘要：

  苯基乙腈与 (2E,4E)-1,5-diarylpenta-2,4-dien-1-ones 的区域特异性 1,4-Michael 加成产生了 12 个新的 (E)-3-(2-oxo-2-arylethyl) -2,5-二芳基戊-4-烯腈，产率为77-88%。该方法的优点是底物范围广、条件温和、收率高、选择性好。该方法还可以扩展到克级。

  DOI：

  10.3184/174751918x15314820245660
• 作为产物：
  描述：

  2-nitrocinnamaldehyde 、 2-乙酰基呋喃 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 (2E,4E)-1-(furan-2-yl)-5-(2-nitrophenyl)penta-2,4-dien-1-one
  参考文献：
  名称：

  One-pot synthesis of cinnamylideneacetophenones and their in vitro cytotoxicity in breast cancer cells

  摘要：

  A series of cinnamylideneacetophenones were synthesized via a modified Claisen-Schmidt condensation reaction and evaluated for cytotoxicity against breast cancer cells using the Alamar Blue (TM) assay. Derivatives 17 and 18 bearing a 2-nitro group on the B ring, exhibited sub-micromolar cytotoxicity in MCF-7 cells (IC50 = 71 and 1.9 nM), respectively. Derivative 17 also displayed sub-micromolar (IC50 = 780 nM) cytotoxicity in MDA-MB-468 cells. Additionally, 17 and 18 displayed significantly less cytotoxicity than the chemotherapeutic doxorubicin in non-tumorigenic MCF-10A cells. This study provides evidence supporting the continued development of nitro-substituted cinnamylideneacetophenones as small molecules to treat breast cancer. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.089

文献信息

• One-pot synthesis of cinnamylideneacetophenones and their in vitro cytotoxicity in breast cancer cells
  作者：David J. Weldon、Marilyn D. Saulsbury、Joshua Goh、Leah Rowland、Petreena Campbell、Laijia Robinson、Calvin Miller、Joshua Christian、Louisa Amis、Nia Taylor、Cassandra Dill、Willie Davis、Stanley L. Evans、Eileen Brantley

  DOI：10.1016/j.bmcl.2014.05.089

  日期：2014.8

  A series of cinnamylideneacetophenones were synthesized via a modified Claisen-Schmidt condensation reaction and evaluated for cytotoxicity against breast cancer cells using the Alamar Blue (TM) assay. Derivatives 17 and 18 bearing a 2-nitro group on the B ring, exhibited sub-micromolar cytotoxicity in MCF-7 cells (IC50 = 71 and 1.9 nM), respectively. Derivative 17 also displayed sub-micromolar (IC50 = 780 nM) cytotoxicity in MDA-MB-468 cells. Additionally, 17 and 18 displayed significantly less cytotoxicity than the chemotherapeutic doxorubicin in non-tumorigenic MCF-10A cells. This study provides evidence supporting the continued development of nitro-substituted cinnamylideneacetophenones as small molecules to treat breast cancer. (C) 2014 Elsevier Ltd. All rights reserved.
• Regiospecific 1,4-Michael Addition of Phenylacetonitrile to 1,5-Diarylpenta-2,4-Dien-1-Ones
  作者：Zheng Li、Wenli Song

  DOI：10.3184/174751918x15314820245660

  日期：2018.7

  The regiospecific 1,4-Michael addition of phenylacetonitrile to (2E,4E)-1,5-diarylpenta-2,4-dien-1-ones produced 12 novel (E)-3-(2-oxo-2-arylethyl)-2,5-diarylpent-4-enenitriles in 77-88% yield. The advantages of the method are broad substrate scope, mild conditions, good to high yields and high selectivity. The method can also be extended to a gram scale.

  苯基乙腈与 (2E,4E)-1,5-diarylpenta-2,4-dien-1-ones 的区域特异性 1,4-Michael 加成产生了 12 个新的 (E)-3-(2-oxo-2-arylethyl) -2,5-二芳基戊-4-烯腈，产率为77-88%。该方法的优点是底物范围广、条件温和、收率高、选择性好。该方法还可以扩展到克级。