2-(7-isopropyl-1-methylazulen-4-yl)ethyl N-succinimidyl carbonate | 1192215-18-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(7-isopropyl-1-methylazulen-4-yl)ethyl N-succinimidyl carbonate
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) 2-(1-methyl-7-propan-2-ylazulen-4-yl)ethyl carbonate；(2,5-dioxopyrrolidin-1-yl) 2-(1-methyl-7-propan-2-ylazulen-4-yl)ethyl carbonate
• CAS: 1192215-18-1
• 化学式: C₂₁H₂₃NO₅
• 分子量: 369.417
• InChiKey: AYQCKDPYNCNCDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-谷氨酸 、 2-(7-isopropyl-1-methylazulen-4-yl)ethyl N-succinimidyl carbonate 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 以86%的产率得到N-[2-(7-isopropyl-1-methylazulen-4-yl)ethoxycarbonyl]-L-glutamic acid
  参考文献：
  名称：

  Coloring Carbohydrates: Investigation of Azulene Derivatives as Blue Protecting Groups

  摘要：

  Coloring carbohydrate derivatives by a chromophore tag greatly facilitates all purification steps during a synthetic sequence, according to a methodology called "chromophore- supported purification" (CSP). Herein an Fmoc-analogous blue protective group for CSP is introduced, based on guaiazulene. Following a mechanistic rational, the synthesis and introduction of this new protecting group is shown, together with its removal under variable conditions and its application for the synthesis of glycoclusters of a glycopeptide and glycopeptoid type.

  DOI：

  10.1080/07328300903040214
• 作为产物：
  描述：

  4-(2-hydroxyethyl)-7-isopropyl-1-methylazulene 、 N,N'-二琥珀酰亚胺基碳酸酯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以99%的产率得到2-(7-isopropyl-1-methylazulen-4-yl)ethyl N-succinimidyl carbonate
  参考文献：
  名称：

  Coloring Carbohydrates: Investigation of Azulene Derivatives as Blue Protecting Groups

  摘要：

  Coloring carbohydrate derivatives by a chromophore tag greatly facilitates all purification steps during a synthetic sequence, according to a methodology called "chromophore- supported purification" (CSP). Herein an Fmoc-analogous blue protective group for CSP is introduced, based on guaiazulene. Following a mechanistic rational, the synthesis and introduction of this new protecting group is shown, together with its removal under variable conditions and its application for the synthesis of glycoclusters of a glycopeptide and glycopeptoid type.

  DOI：

  10.1080/07328300903040214

文献信息

• Coloring Carbohydrates: Investigation of Azulene Derivatives as Blue Protecting Groups
  作者：Ingo B. Aumüller、Thisbe K. Lindhorst

  DOI：10.1080/07328300903040214

  日期：2009.7.29

  Coloring carbohydrate derivatives by a chromophore tag greatly facilitates all purification steps during a synthetic sequence, according to a methodology called "chromophore- supported purification" (CSP). Herein an Fmoc-analogous blue protective group for CSP is introduced, based on guaiazulene. Following a mechanistic rational, the synthesis and introduction of this new protecting group is shown, together with its removal under variable conditions and its application for the synthesis of glycoclusters of a glycopeptide and glycopeptoid type.