(S)-tert-butyl 3-(4-tert-butoxyphenyl)-1-((2,5-dimethoxy-3,6-dioxocyclohexa-1,4-dienyl)methylamino)-1-oxopropan-2-ylcarbamate | 1380092-40-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-tert-butyl 3-(4-tert-butoxyphenyl)-1-((2,5-dimethoxy-3,6-dioxocyclohexa-1,4-dienyl)methylamino)-1-oxopropan-2-ylcarbamate
• 英文别名: tert-butyl N-[(2S)-1-[(2,5-dimethoxy-3,6-dioxocyclohexa-1,4-dien-1-yl)methylamino]-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]-1-oxopropan-2-yl]carbamate
• CAS: 1380092-40-9
• 化学式: C₂₇H₃₆N₂O₈
• 分子量: 516.591
• InChiKey: LTYATOOTZRNUHW-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 3-(4-tert-butoxyphenyl)-1-((2,5-dimethoxy-3,6-dioxocyclohexa-1,4-dienyl)methylamino)-1-oxopropan-2-ylcarbamate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以74%的产率得到(S)-1-((2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)methylamino)-3-(4-hydroxyphenyl)-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-hydroxy-3,5,6-trimethoxybenzaldehyde 在 碘苯二乙酸 、 t-butyldimethylsilane 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 18.75h， 生成 (S)-tert-butyl 3-(4-tert-butoxyphenyl)-1-((2,5-dimethoxy-3,6-dioxocyclohexa-1,4-dienyl)methylamino)-1-oxopropan-2-ylcarbamate
  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