3-(bromomethyl)-4'-methoxyflavone | 905601-29-8

• 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: 3-(bromomethyl)-4'-methoxyflavone
• 英文别名: 3-bromomethyl-4′-methoxyflavone；3-(Bromomethyl)-2-(4-methoxyphenyl)chromen-4-one
• CAS: 905601-29-8
• 化学式: C₁₇H₁₃BrO₃
• 分子量: 345.192
• InChiKey: UEMDKPMMGJWIHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(bromomethyl)-4'-methoxyflavone 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 26.5h， 生成 2-(4-methoxyphenyl)-3-[(E)-2-phenylethenyl]chromen-4-one
  参考文献：
  名称：

  One-Pot Synthesis of 3-Methylflavones and Their Transformation into (E)-3-Styrylflavones via Wittig Reactions

  摘要：

  An efficient one-pot synthesis of 3-methylflavone derivatives is established. Furthermore, their transformation into phosphorus ylides, which are then used in the diastereoselective synthesis of (E)-styrylflavones through Wittig reactions, is also studied.

  DOI：

  10.1055/s-0033-1340013
• 作为产物：
  描述：

  2'-羟基苯丙酮 在 N-溴代丁二酰亚胺(NBS) 、 lithium hexamethyldisilazane 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 50.5h， 生成 3-(bromomethyl)-4'-methoxyflavone
  参考文献：
  名称：

  One-Pot Synthesis of 3-Methylflavones and Their Transformation into (E)-3-Styrylflavones via Wittig Reactions

  摘要：

  An efficient one-pot synthesis of 3-methylflavone derivatives is established. Furthermore, their transformation into phosphorus ylides, which are then used in the diastereoselective synthesis of (E)-styrylflavones through Wittig reactions, is also studied.

  DOI：

  10.1055/s-0033-1340013

文献信息

• Lead Optimization Providing a Series of Flavone Derivatives as Potent Nonsteroidal Inhibitors of the Cytochrome P450 Aromatase Enzyme
  作者：Silvia Gobbi、Andrea Cavalli、Angela Rampa、Federica Belluti、Lorna Piazzi、Anja Paluszcak、Rolf W. Hartmann、Maurizio Recanatini、Alessandra Bisi

  DOI：10.1021/jm060186y

  日期：2006.7.1

  Following our SAR studies on aromatase inhibitors, new compounds were designed by appropriately modifying the structure of flavone 1 using our previously reported CoMFA model. While the introduction of substituents on the 2-phenyl ring alone did not cause improvement in potency, these modifications and the removal of the 7-methoxy group led to compounds showing inhibitory activity in the nanomolar range, comparable to the marketed drug fadrozole.
• One-Pot Synthesis of 3-Methylflavones and Their Transformation into (E)-3-Styrylflavones via Wittig Reactions
  作者：Diana Pinto、Artur Silva、Djenisa Rocha

  DOI：10.1055/s-0033-1340013

  日期：——

  An efficient one-pot synthesis of 3-methylflavone derivatives is established. Furthermore, their transformation into phosphorus ylides, which are then used in the diastereoselective synthesis of (E)-styrylflavones through Wittig reactions, is also studied.