tert-butyl 2-hydroxy-3,5,6-trimethoxybenzylcarbamate | 1380092-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: tert-butyl 2-hydroxy-3,5,6-trimethoxybenzylcarbamate
• CAS: 1380092-15-8
• 化学式: C₁₅H₂₃NO₆
• 分子量: 313.351
• InChiKey: RCBYBAWOJQEANI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  86.25
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-hydroxy-3,5,6-trimethoxybenzylcarbamate 在 盐酸 、 碘苯二乙酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 48.75h， 生成 (S)-1-((2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)methylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-aminium chloride
  参考文献：
  名称：

  Synthesis and biological evaluation of hydrophilic embelin derivatives

  摘要：

  In continuance of our search for newer anti-cancer agents we were interested on embelin, a XIAP (X-linked inhibitor of apoptosis protein) inhibitor. This natural benzoquinone bear a lipophilic chain and we report here the synthesis of hydrophilic analogues of embelin. To allow a large flexibility in the nature of the hydrophilic group, three amines with different length of carbon chain bearing a protected benzoquinone were prepared. The cytotoxic effects of these derivatives were evaluated on KB cell line. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.024
• 作为产物：
  描述：

  2,4,5-三甲氧基苯酚 在 t-butyldimethylsilane 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 40.0h， 生成 tert-butyl 2-hydroxy-3,5,6-trimethoxybenzylcarbamate
  参考文献：
  名称：

  Synthesis and biological evaluation of hydrophilic embelin derivatives

  摘要：

  In continuance of our search for newer anti-cancer agents we were interested on embelin, a XIAP (X-linked inhibitor of apoptosis protein) inhibitor. This natural benzoquinone bear a lipophilic chain and we report here the synthesis of hydrophilic analogues of embelin. To allow a large flexibility in the nature of the hydrophilic group, three amines with different length of carbon chain bearing a protected benzoquinone were prepared. The cytotoxic effects of these derivatives were evaluated on KB cell line. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.024