4-chloro-6-phenyl-2-pyrone | 1259313-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-chloro-6-phenyl-2-pyrone
• 英文别名: 4-Chloro-6-phenylpyran-2-one；4-chloro-6-phenylpyran-2-one
• CAS: 1259313-09-1
• 化学式: C₁₁H₇ClO₂
• 分子量: 206.628
• InChiKey: MZXCKBHIACGVCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-碘苯酚 、 4-chloro-6-phenyl-2-pyrone 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以82.9%的产率得到4-(2-iodophenoxy)-6-phenyl-2-pyrone
  参考文献：
  名称：

  Pd-catalysed regioselective C–H functionalisation of 2-pyrones

  摘要：

  描述了一种新的合成方法，用于催化2-吡喃的C–H官能化，该反应在C3位点以选择性的方式进行，这与相关化合物在6π-电环化/氧化芳构化反应中观察到的区位选择性相呼应。提供了对反应机制的见解，支持中性钯(II)途径。具有2-吡喃的阳离子钯(II)配合物不稳定，容易在常温下发生PdII↔P转移，导致磷盐形成（以及Pd0Ln物种）。

  DOI：

  10.1039/c0dt00421a
• 作为产物：
  描述：

  4-羟基-6-苯基吡喃-2-酮 在 三乙胺 、 三氯氧磷 作用下， 反应 1.0h， 生成 4-chloro-6-phenyl-2-pyrone
  参考文献：
  名称：

  Antitumor agents 287. Substituted 4-amino-2H-pyran-2-one (APO) analogs reveal a new scaffold from neo-tanshinlactone with in vitro anticancer activity

  摘要：

  4-Amino-2H-benzo[h] chromen-2-one (ABO) and 4-amino-7,8,9,10-tetrahydro-2H-benzo[h] chromen-2-one (ATBO) analogs were found to be significant in vitro anticancer agents in our previous research. Our continuing study has now discovered a new simplified (monocyclic rather than tricyclic) class of cytotoxic agents, 4-amino-2H-pyran-2-one (APO) analogs. By incorporating various substituents on the pyranone ring, we have established preliminary structure-activity relationships (SAR). Analogs 19, 20, 23, and 26-30 displayed significant tumor cell growth inhibitory activity in vitro. The most active compound 27 exhibited ED50 values of 0.059-0.090 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.084

文献信息

• Pd-catalysed regioselective C–H functionalisation of 2-pyrones
  作者：Michael J. Burns、Robert J. Thatcher、Richard J. K. Taylor、Ian J. S. Fairlamb

  DOI：10.1039/c0dt00421a

  日期：——

  A new synthetic methodology for the catalytic C–H functionalisation of 2-pyrones is described which proceeds regioselectively at the C3 position, mirroring the observed regioselectivity in 6π-electrocyclisation/oxidative aromatisation reactions of related compounds. Insight into the reaction mechanism is provided, with support for a neutral palladium(II) pathway. Cationic palladium(II) complexes possessing 2-pyrones are unstable and readily undergo PdII→P transfer at ambient temperature resulting in phosphonium salt formation (and Pd0Ln species).

  描述了一种新的合成方法，用于催化2-吡喃的C–H官能化，该反应在C3位点以选择性的方式进行，这与相关化合物在6π-电环化/氧化芳构化反应中观察到的区位选择性相呼应。提供了对反应机制的见解，支持中性钯(II)途径。具有2-吡喃的阳离子钯(II)配合物不稳定，容易在常温下发生PdII↔P转移，导致磷盐形成（以及Pd0Ln物种）。
• Antitumor agents 287. Substituted 4-amino-2H-pyran-2-one (APO) analogs reveal a new scaffold from neo-tanshinlactone with in vitro anticancer activity
  作者：Yizhou Dong、Kyoko Nakagawa-Goto、Chin-Yu Lai、Susan L. Morris-Natschke、Kenneth F. Bastow、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2011.02.084

  日期：2011.4

  4-Amino-2H-benzo[h] chromen-2-one (ABO) and 4-amino-7,8,9,10-tetrahydro-2H-benzo[h] chromen-2-one (ATBO) analogs were found to be significant in vitro anticancer agents in our previous research. Our continuing study has now discovered a new simplified (monocyclic rather than tricyclic) class of cytotoxic agents, 4-amino-2H-pyran-2-one (APO) analogs. By incorporating various substituents on the pyranone ring, we have established preliminary structure-activity relationships (SAR). Analogs 19, 20, 23, and 26-30 displayed significant tumor cell growth inhibitory activity in vitro. The most active compound 27 exhibited ED50 values of 0.059-0.090 mu M. (C) 2011 Elsevier Ltd. All rights reserved.