(S)-tert-butyl 3-tert-butoxy-1-((2,5-dimethoxy-3,6-dioxocyclohexa-1,4-dienyl)methylamino)-1-oxopropan-2-ylcarbamate | 1380092-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-tert-butyl 3-tert-butoxy-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-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]carbamate
• CAS: 1380092-36-3
• 化学式: C₂₁H₃₂N₂O₈
• 分子量: 440.494
• InChiKey: MRQAJHFSIUSHKD-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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-tert-butoxy-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88%的产率得到(S)-1-((2,5-dihydroxy-3,6-dioxocyclohexa-1,4-dienyl)methylamino)-3-hydroxy-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：

  (S)-tert-butyl 3-tert-butoxy-1-(2-hydroxy-3,5,6-trimethoxybenzylamino)-1-oxopropan-2-ylcarbamate 在 碘苯二乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 以70%的产率得到(S)-tert-butyl 3-tert-butoxy-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