(2R)-2-(4-benzyloxyphenyl)-7-benzyloxychroman-3-one | 850816-07-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2R)-2-(4-benzyloxyphenyl)-7-benzyloxychroman-3-one
• 英文别名: (2R)-7-phenylmethoxy-2-(4-phenylmethoxyphenyl)-4H-chromen-3-one
• CAS: 850816-07-8
• 化学式: C₂₉H₂₄O₄
• 分子量: 436.507
• InChiKey: FYDCIRCJVUCRRT-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-2-(4-benzyloxyphenyl)-7-benzyloxychroman-3-one 在 4-二甲氨基吡啶 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 L-Selectride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 (2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman-3-yl acetate
  参考文献：
  名称：

  (+)-Myristinin A, a Naturally Occurring DNA Polymerase β Inhibitor and Potent DNA-Damaging Agent

  摘要：

  The first stereoselective total synthesis of the naturally occurring flavan myristinin A has been accomplished, as well as its biochemical evaluation. This synthesis verified the structural assignment and allowed for the determination of the absolute stereochemistry. Myristinin A exhibits biochemical activity both as a potent DNA-damaging agent and DNA polymerase beta inhibitor. Relaxation of supercoiled plasmid DNA was observed at picomolar concentrations, in addition to inhibition of polymerase beta at low micromolar concentrations.

  DOI：

  10.1021/ja042727j
• 作为产物：
  描述：

  (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one 在 咪唑 、 AD-mix-α 、 甲基磺酰胺 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 氯甲酸乙酯 、 potassium carbonate 、 戴斯-马丁氧化剂 、 三乙胺 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 9.5h， 生成 (2R)-2-(4-benzyloxyphenyl)-7-benzyloxychroman-3-one
  参考文献：
  名称：

  (+)-Myristinin A, a Naturally Occurring DNA Polymerase β Inhibitor and Potent DNA-Damaging Agent

  摘要：

  The first stereoselective total synthesis of the naturally occurring flavan myristinin A has been accomplished, as well as its biochemical evaluation. This synthesis verified the structural assignment and allowed for the determination of the absolute stereochemistry. Myristinin A exhibits biochemical activity both as a potent DNA-damaging agent and DNA polymerase beta inhibitor. Relaxation of supercoiled plasmid DNA was observed at picomolar concentrations, in addition to inhibition of polymerase beta at low micromolar concentrations.

  DOI：

  10.1021/ja042727j

文献信息

• (+)-Myristinin A, a Naturally Occurring DNA Polymerase β Inhibitor and Potent DNA-Damaging Agent
  作者：David J. Maloney、Jing-Zhen Deng、Shelley R. Starck、Zhijie Gao、Sidney M. Hecht

  DOI：10.1021/ja042727j

  日期：2005.3.1

  The first stereoselective total synthesis of the naturally occurring flavan myristinin A has been accomplished, as well as its biochemical evaluation. This synthesis verified the structural assignment and allowed for the determination of the absolute stereochemistry. Myristinin A exhibits biochemical activity both as a potent DNA-damaging agent and DNA polymerase beta inhibitor. Relaxation of supercoiled plasmid DNA was observed at picomolar concentrations, in addition to inhibition of polymerase beta at low micromolar concentrations.