N-(Chlorosulfonyl)-exo-3-aza-4-ketotricyclo<4.2.1.0^2,5>nonane | 14932-21-9

• 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: N-(Chlorosulfonyl)-exo-3-aza-4-ketotricyclo<4.2.1.0^2,5>nonane
• 英文别名: N-(Chlorosulfonyl)-exo-3-aza-4-ketotricyclo[4.2.1.0^2,5]nonane；(1R,2S,5R,6S)-4-oxo-3-azatricyclo[4.2.1.02,5]nonane-3-sulfonyl chloride
• CAS: 14932-21-9
• 化学式: C₈H₁₀ClNO₃S
• 分子量: 235.691
• InChiKey: FKQJRNXBRYVEDG-WNJXEPBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(Chlorosulfonyl)-exo-3-aza-4-ketotricyclo<4.2.1.0^2,5>nonane 在 盐酸 、 水 、 sodium hydroxide 、 sodium sulfite 作用下， 以 水 为溶剂， 生成 (±)-cis-3-aminobicyclo[2.2.1]heptane-2-carboxylic acid hydrochloride
  参考文献：
  名称：

  Large-Scale Syntheses of FMOC-Protected Non-Proteogenic Amino Acids:  Useful Building Blocks for Combinatorial Libraries

  摘要：

  Convenient and reliable large-scale procedures for the protection of various amino acids with N-(9-fluorenyimethoxycarbonyl)oxysuccinimide (FMOC-OSu) are described. Commercially available 4-aminomethylbenzoic acid and trans-4-(aminomethyl)cyclohexanecarboxylic acid were converted into their corresponding FMOC-derivatives in excellent yields without the need for an extractive workup. In addition, FMOC-cis-beta -amino acids were also prepared, employing a [2 + 2]-cycloaddition strategy between a cyclic olefin and N-chlorosulfonyl isocyanate (CSI). The resulting N-chlorosulfonyl fl-lactams were reduced to the parent beta -lactams with sodium sulfite and then converted to the cis-fi-amino acid hydrochlorides by exposure to aqueous hydrochloric acid. The resulting cis-fi-amino acids were converted to their FMOC-derivatives under conditions similar to those developed for the commercially available amino acids. Differences in the conditions employed between these beta -amino acids and the commercial derivatives were observed, primarily in the nature of the base required for the reaction. A possible rationale for the differences in behavior is described. These FMOC-amino acid derivatives are valuable intermediates for the solid-phase synthesis of combinatorial libraries.

  DOI：

  10.1021/op010204f
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 norbornene 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-(Chlorosulfonyl)-exo-3-aza-4-ketotricyclo<4.2.1.0^2,5>nonane
  参考文献：
  名称：

  Large-Scale Syntheses of FMOC-Protected Non-Proteogenic Amino Acids:  Useful Building Blocks for Combinatorial Libraries

  摘要：

  Convenient and reliable large-scale procedures for the protection of various amino acids with N-(9-fluorenyimethoxycarbonyl)oxysuccinimide (FMOC-OSu) are described. Commercially available 4-aminomethylbenzoic acid and trans-4-(aminomethyl)cyclohexanecarboxylic acid were converted into their corresponding FMOC-derivatives in excellent yields without the need for an extractive workup. In addition, FMOC-cis-beta -amino acids were also prepared, employing a [2 + 2]-cycloaddition strategy between a cyclic olefin and N-chlorosulfonyl isocyanate (CSI). The resulting N-chlorosulfonyl fl-lactams were reduced to the parent beta -lactams with sodium sulfite and then converted to the cis-fi-amino acid hydrochlorides by exposure to aqueous hydrochloric acid. The resulting cis-fi-amino acids were converted to their FMOC-derivatives under conditions similar to those developed for the commercially available amino acids. Differences in the conditions employed between these beta -amino acids and the commercial derivatives were observed, primarily in the nature of the base required for the reaction. A possible rationale for the differences in behavior is described. These FMOC-amino acid derivatives are valuable intermediates for the solid-phase synthesis of combinatorial libraries.

  DOI：

  10.1021/op010204f

文献信息

• Catalysis of .alpha.-hydrogen exchange. Part 23. Six-at-once dedeuteration of acetone-d6 in the presence of 3-exo-[(dimethylamino)methyl]-2-exo-norbornanamine
  作者：Jack Hine、Hwai Min Tsay

  DOI：10.1021/jo00169a039

  日期：1983.10