(2E,5E)-2,5-bis(pyridin-2-ylmethylene)cyclopentanone | 47084-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (2E,5E)-2,5-bis(pyridin-2-ylmethylene)cyclopentanone
• 英文别名: (2E,5E)-2,5-bis(pyridine-2-methylene)cyclopentanone；2,5-bis[(E)-(2-pyridyl)methylidene]cyclopentanone；(2E,6E)-2,6-bis(pyridin-2-methylene)cyclopentanone；(2E,5E)-2,5-Bis[(pyridin-2-YL)methylidene]cyclopentan-1-one；(2E,5E)-2,5-bis(pyridin-2-ylmethylidene)cyclopentan-1-one
• CAS: 47084-34-4
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: XYTZNQXEAFGUJR-PHEQNACWSA-N

物化性质

• 沸点：
  493.3±45.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,5E)-2,5-bis(pyridin-2-ylmethylene)cyclopentanone 生成 (2E,5E)-2,5-bis(pyridin-2-ylmethylidene)cyclopentan-1-ol
  参考文献：
  名称：

  KATRITZKY, ALAN R.;FAN, WEI-QIANG;JIAO, XUE-SHUN;LI, QIAO-LING, J. HETEROCYCL. CHEM., 25,(1988) N, C. 1321-1325

  摘要：

  DOI：
• 作为产物：
  描述：

  吡啶-2-甲醛 、 环戊酮 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 10.0h， 以69%的产率得到(2E,5E)-2,5-bis(pyridin-2-ylmethylene)cyclopentanone
  参考文献：
  名称：

  衍生自环酮和芳香醛的交叉共轭二烯酮的合成、光谱和结构研究

  摘要：

  交叉共轭二烯酮是通过环状酮与两当量的芳香醛在碱性条件下反应合成的。NMR 光谱研究和 X 射线衍射分析表明，所有反应产物均以 E、E 异构体的形式形成。首次观察到溶液中散射光下交叉共轭二烯酮的自发光化学反顺异构化。异构化程度主要取决于二烯酮分子中心片段的性质。合成了以前未知的 2,5-双 [(E)-(3-吡啶基) 亚甲基] 环戊酮的光化学 [2+2]-环加成产物，并通过光谱方法和 X 射线衍射进行了表征。在所使用的条件下，仅获得环丁烷加合物的一种异构体。

  DOI：

  10.1007/s11172-006-0397-6

文献信息

• Water promoted C–C bond cleavage: facile synthesis of 3,3-bipyrrole derivatives from dienones and tosylmethyl isocyanide (TosMIC)
  作者：Rong Wang、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1039/c3ob42570c

  日期：——

  A simple and highly efficient synthetic strategy to access 3,3-bipyrrole derivatives by the reaction of dienone derivatives with TosMIC is reported. The reaction involves a van Leusen's pyrrole synthesis followed by an unusual C–C bond cleavage in the presence of water under mild conditions.

  本报告介绍了一种通过二烯酮衍生物与 TosMIC 反应获得 3,3-联吡咯衍生物的简单而高效的合成策略。该反应涉及 van Leusen 的吡咯合成，然后在温和的条件下，在有水存在的情况下进行不寻常的 CâC 键裂解。
• Synthesis and evaluation of curcumin-related compounds for anticancer activity
  作者：Xingchuan Wei、Zhi-Yun Du、Xi Zheng、Xiao-Xing Cui、Allan H. Conney、Kun Zhang

  DOI：10.1016/j.ejmech.2012.04.005

  日期：2012.7

  Sixty-one curcumin-related compounds were synthesized and evaluated for their anticancer activity toward cultured prostate cancer PC-3 cells, pancreas cancer Panc-1 cells and colon cancer HT-29 cells. Inhibitory effects of these compounds on the growth of PC-3. Panc-1 and HT-29 cells were determined by the MTT assay. Compounds E10, F10, FN1 and FN2 exhibited exceptionally potent inhibitory effects on the growth of cultured PC-3, Panc-1 and HT-29 cells. The IC50 for these compounds was lower than 1 mu M in all three cell lines. E10 was 72-, 46- and 117-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. F10 was 69-, 34- and 72-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. FN1 and FN2 had about the same inhibitory effect as E10 and F10 toward Panc-1 cells but were less active than E10 and F10 toward PC-3 and HT-29 cells. The active compounds were potent stimulators of apoptosis. The present study indicates that E10, F10, FN1 and FN2 may have useful anticancer activity. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Desiraju, Gautam R.; Radha Kishan, K. V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 953 - 954
  作者：Desiraju, Gautam R.、Radha Kishan, K. V.

  DOI：——

  日期：——
• DESIRAJU, GAUTAM R.;KISHAN, K. V. RADHA, INDIAN J. CHEM. B, 27,(1988) N0, C. 953-954
  作者：DESIRAJU, GAUTAM R.、KISHAN, K. V. RADHA

  DOI：——

  日期：——
• Synthesis and spectroscopic and structural studies of cross-conjugated dienones derived from cyclic ketones and aromatic aldehydes
  作者：S. Z. Vatsadze、M. A. Manaenkova、N. V. Sviridenkova、N. V. Zyk、D. P. Krut’ko、A. V. Churakov、M. Yu. Antipin、J. A. K. Howard、H. Lang

  DOI：10.1007/s11172-006-0397-6

  日期：2006.7

  Cross-conjugated dienones were synthesized by the reactions of cyclic ketones with two equivalents of aromatic aldehydes under basic conditions. An NMR spectroscopic study and X-ray diffraction analysis demonstrated that all reaction products are formed as E,E isomers. Spontaneous photochemical trans-cis isomerization of cross-conjugated dienones under the scattered light in solution was observed for

  交叉共轭二烯酮是通过环状酮与两当量的芳香醛在碱性条件下反应合成的。NMR 光谱研究和 X 射线衍射分析表明，所有反应产物均以 E、E 异构体的形式形成。首次观察到溶液中散射光下交叉共轭二烯酮的自发光化学反顺异构化。异构化程度主要取决于二烯酮分子中心片段的性质。合成了以前未知的 2,5-双 [(E)-(3-吡啶基) 亚甲基] 环戊酮的光化学 [2+2]-环加成产物，并通过光谱方法和 X 射线衍射进行了表征。在所使用的条件下，仅获得环丁烷加合物的一种异构体。