2-(4-methoxybenzylidene)-1,3-bis(3,4,5-trimethoxyphenyl)-1,3-propadione | 608533-34-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-(4-methoxybenzylidene)-1,3-bis(3,4,5-trimethoxyphenyl)-1,3-propadione
• 英文别名: 2-(4-methoxybenzylidene)-1,3-bis(3,4,5-trimethoxyphenyl)propane-1,3-dione；2-[(4-Methoxyphenyl)methylidene]-1,3-bis(3,4,5-trimethoxyphenyl)propane-1,3-dione；2-[(4-methoxyphenyl)methylidene]-1,3-bis(3,4,5-trimethoxyphenyl)propane-1,3-dione
• CAS: 608533-34-2
• 化学式: C₂₉H₃₀O₉
• 分子量: 522.552
• InChiKey: YFJYAFADLLHHLM-UHFFFAOYSA-N

物化性质

• 熔点：
  49-50 °C
• 沸点：
  704.7±60.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(4-methoxybenzylidene)-1,3-bis(3,4,5-trimethoxyphenyl)-1,3-propadione 在 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(+/-)-4,5,6-trimethoxy-3-(4-methoxyphenyl)-2-(3,4,5-trimethoxybenzoyl)indan-1-one
  参考文献：
  名称：

  Kerr, Daniel J.; Metje, Christiane; Flynn, Bernard L., Chemical Communications, 2003, # 12, p. 1380 - 1381

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 正丁基锂 、 三正丁基氢锡 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(4-methoxybenzylidene)-1,3-bis(3,4,5-trimethoxyphenyl)-1,3-propadione
  参考文献：
  名称：

  The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4

  摘要：

  A series of aryl- and aroyl-substituted chalcone analogues of the tubulin binding agent combretastatin A4 (1) were prepared, using a recently introduced one-pot palladium-mediated hydrostannylation-coupling reaction sequence. These chalcones were converted to indanones by Nazarov cyclisation, followed by oxidation to give the corresponding indenones. Indenones were also prepared using a palladium-mediated formal [3+2]-cycloaddition process between ortho-halobenzaldehydes and diarylpropynones. All compounds were assessed as inhibitors of tubulin polymerisation, but only E-31 had activity similar to that of 1. However, compound E-31 did not exhibit antiproliferative activity against the MCF-7 cell line. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.006

文献信息

• A Reductive-Coupling plus Nazarov Cyclization Sequence in the Asymmetric Synthesis of Five-Membered Carbocycles
  作者：Daniel J. Kerr、Jonathan M. White、Bernard L. Flynn

  DOI：10.1021/jo100736p

  日期：2010.11.5

  Palladium-mediated hydrostannylation of alkynoyl compounds is combined with Stille-Scott cross-coupling (reductive-coupling) to give one-pot access to divinyl and aryl vinyl ketones, which undergo Nazarov cyclization to give cyclopentenones upon treatment with acid. This reaction sequence has been studied with a variety of different substitution patterns, including the use of oxazolidinone auxiliaries to achieve torquoselectivity in the Nazarov cyclization. Through a combination of good yields and moderate to good levels of stereochemical induction, this approach affords efficient, convergent, and asymmetric access to a variety of different cyclopentanoid systems.
• Kerr, Daniel J.; Metje, Christiane; Flynn, Bernard L., Chemical Communications, 2003, # 12, p. 1380 - 1381
  作者：Kerr, Daniel J.、Metje, Christiane、Flynn, Bernard L.

  DOI：——

  日期：——
• The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4
  作者：Daniel J. Kerr、Ernest Hamel、M. Katherine Jung、Bernard L. Flynn

  DOI：10.1016/j.bmc.2007.02.006

  日期：2007.5

  A series of aryl- and aroyl-substituted chalcone analogues of the tubulin binding agent combretastatin A4 (1) were prepared, using a recently introduced one-pot palladium-mediated hydrostannylation-coupling reaction sequence. These chalcones were converted to indanones by Nazarov cyclisation, followed by oxidation to give the corresponding indenones. Indenones were also prepared using a palladium-mediated formal [3+2]-cycloaddition process between ortho-halobenzaldehydes and diarylpropynones. All compounds were assessed as inhibitors of tubulin polymerisation, but only E-31 had activity similar to that of 1. However, compound E-31 did not exhibit antiproliferative activity against the MCF-7 cell line. (c) 2007 Elsevier Ltd. All rights reserved.