4-(4,5-bis(benzyloxy)-2-chlorophenyl)-7-bromo-6-(methoxymethoxy)benzo[d][1,3]dioxole-5-carbaldehyde | 1192737-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-(4,5-bis(benzyloxy)-2-chlorophenyl)-7-bromo-6-(methoxymethoxy)benzo[d][1,3]dioxole-5-carbaldehyde
• 英文别名: 7-Bromo-4-[2-chloro-4,5-bis(phenylmethoxy)phenyl]-6-(methoxymethoxy)-1,3-benzodioxole-5-carbaldehyde
• CAS: 1192737-18-0
• 化学式: C₃₀H₂₄BrClO₇
• 分子量: 611.873
• InChiKey: NICOOLUVJQITBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(4,5-bis(benzyloxy)-2-chlorophenyl)-7-bromo-6-(methoxymethoxy)benzo[d][1,3]dioxole-5-carbaldehyde 、 4-苄氧基苯硼酸 在 potassium phosphate 、 palladium diacetate 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以91%的产率得到7-(4-(benzyloxy)phenyl)-4-(4,5-bis(benzyloxy)-2-chlorophenyl)-6-(methoxymethoxy)benzo-[d][1,3]dioxole-5-carbaldehyde
  参考文献：
  名称：

  Expeditious Synthesis of Vialinin B, an Extremely Potent Inhibitor of TNF-α Production

  摘要：

  A first total synthesis of vialinin B, a powerful inhibitor (IC50 20 pM) of TNF-alpha production, is described. The key reactions include a double Suzuki-Miyaura coupling of electron-rich aryl bromide with a couple of phenylboronic acids, a Cu-mediated Ullmann reaction, and a LHMDS-promoted phenylacetylation. This synthesis proceeded in 11 steps with 18% overall yield from a known sesamol derivative.

  DOI：

  10.1021/ol9020833
• 作为产物：
  描述：

  4,7-dibromo-6-(methoxymethoxy)benzo[d][1,3]dioxole-5-carbaldehyde 、 3,4-dibenzyloxy-6-chlorophenyl boronic acid 在 potassium phosphate 、 palladium diacetate 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.5h， 以78%的产率得到4-(4,5-bis(benzyloxy)-2-chlorophenyl)-7-bromo-6-(methoxymethoxy)benzo[d][1,3]dioxole-5-carbaldehyde
  参考文献：
  名称：

  Expeditious Synthesis of Vialinin B, an Extremely Potent Inhibitor of TNF-α Production

  摘要：

  A first total synthesis of vialinin B, a powerful inhibitor (IC50 20 pM) of TNF-alpha production, is described. The key reactions include a double Suzuki-Miyaura coupling of electron-rich aryl bromide with a couple of phenylboronic acids, a Cu-mediated Ullmann reaction, and a LHMDS-promoted phenylacetylation. This synthesis proceeded in 11 steps with 18% overall yield from a known sesamol derivative.

  DOI：

  10.1021/ol9020833

文献信息

• Expeditious Synthesis of Vialinin B, an Extremely Potent Inhibitor of TNF-α Production
  作者：Yue Qi Ye、Hiroyuki Koshino、Jun-ichi Onose、Kunie Yoshikawa、Naoki Abe、Shunya Takahashi

  DOI：10.1021/ol9020833

  日期：2009.11.5

  A first total synthesis of vialinin B, a powerful inhibitor (IC50 20 pM) of TNF-alpha production, is described. The key reactions include a double Suzuki-Miyaura coupling of electron-rich aryl bromide with a couple of phenylboronic acids, a Cu-mediated Ullmann reaction, and a LHMDS-promoted phenylacetylation. This synthesis proceeded in 11 steps with 18% overall yield from a known sesamol derivative.