5,6-bis(phenylacetoxy)-4,7-di(p-(t-butyldimethylsilyloxy)phenyl)benzo[d][1,3]dioxole | 956024-14-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,6-bis(phenylacetoxy)-4,7-di(p-(t-butyldimethylsilyloxy)phenyl)benzo[d][1,3]dioxole
• 英文别名: [4,7-Bis[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-6-(2-phenylacetyl)oxy-1,3-benzodioxol-5-yl] 2-phenylacetate
• CAS: 956024-14-9
• 化学式: C₄₇H₅₄O₈Si₂
• 分子量: 803.112
• InChiKey: WGWNZKYWGQJZLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.81
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,6-bis(phenylacetoxy)-4,7-di(p-(t-butyldimethylsilyloxy)phenyl)benzo[d][1,3]dioxole 在 盐酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 66.0h， 生成 4,4'',5',6'-四羟基-1,1':4',1''-三联苯-2',3'-二基二(苯乙酸酯)
  参考文献：
  名称：

  First Total Synthesis of Vialinin A, a Novel and Extremely Potent Inhibitor of TNF-α Production

  摘要：

  Vialinin A, a powerful inhibitor (IC50 90 pM) of TNF-alpha production, was synthesized from sesamol in 11 steps with 28% overall yield. The key reactions include a double Suzuki coupling of electron-rich aryl triflate with phenylboronic acid and an oxidative deprotection of bis-MOM ether. In addition, the related synthetic studies also suggest the necessity for structural revision of ganbajunin C, a positional isomer of vialinin A.

  DOI：

  10.1021/ol701590b
• 作为产物：
  描述：

  5,6-bis(methoxymethoxy)benzo[d][1,3]dioxole 在 四(三苯基膦)钯 吡啶 、 potassium phosphate 、 正丁基锂 、 sodium dithionite 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium bromide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 水 、 乙酸乙酯 为溶剂， 反应 55.16h， 生成 5,6-bis(phenylacetoxy)-4,7-di(p-(t-butyldimethylsilyloxy)phenyl)benzo[d][1,3]dioxole
  参考文献：
  名称：

  First Total Synthesis of Vialinin A, a Novel and Extremely Potent Inhibitor of TNF-α Production

  摘要：

  Vialinin A, a powerful inhibitor (IC50 90 pM) of TNF-alpha production, was synthesized from sesamol in 11 steps with 28% overall yield. The key reactions include a double Suzuki coupling of electron-rich aryl triflate with phenylboronic acid and an oxidative deprotection of bis-MOM ether. In addition, the related synthetic studies also suggest the necessity for structural revision of ganbajunin C, a positional isomer of vialinin A.

  DOI：

  10.1021/ol701590b

文献信息

• First Total Synthesis of Vialinin A, a Novel and 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/ol701590b

  日期：2007.10.1

  Vialinin A, a powerful inhibitor (IC50 90 pM) of TNF-alpha production, was synthesized from sesamol in 11 steps with 28% overall yield. The key reactions include a double Suzuki coupling of electron-rich aryl triflate with phenylboronic acid and an oxidative deprotection of bis-MOM ether. In addition, the related synthetic studies also suggest the necessity for structural revision of ganbajunin C, a positional isomer of vialinin A.