(1S,4S)-2-[1-Isocyano-meth-(Z)-ylidene]-1,7,7-trimethyl-bicyclo[2.2.1]heptane | 191026-87-6

• 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: (1S,4S)-2-[1-Isocyano-meth-(Z)-ylidene]-1,7,7-trimethyl-bicyclo[2.2.1]heptane
• CAS: 191026-87-6
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: KIJOUNITJZJPDI-RQTFPAPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  4.36
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 特戊醛 、 (1S,4S)-2-[1-Isocyano-meth-(Z)-ylidene]-1,7,7-trimethyl-bicyclo[2.2.1]heptane 以 四氢呋喃 为溶剂， 反应 40.0h， 以89%的产率得到
  参考文献：
  名称：

  Multicomponent reactions. II. Stereoselective synthesis of 1(S)-camphor-2-cis-methylidene-isocyanide and its application in Passerini- and Ugi-reaction

  摘要：

  The use of unsaturated isocyanides in multicomponent reactions leads to N-vinylamides, which can be cleaved to carboxylic acids or esters under mild conditions. The chiral 1 (S)-camphor-2-cis-methylidene-isocyanide (5) can be prepared in two steps from camphor and methylisocyanide. Its application in the Passerini reaction generates alpha-acyloxyamides (6, 7, 8, 9) with a diastereomeric excess of > 92%, in the Ugi reaction alpha-acylaminoamides with a diastereomeric excess of 0% are formed.

  DOI：

  10.1002/prac.19973390167
• 作为产物：
  描述：

  1(S)-camphor-2-exo-5'-spiro-2-oxazoline 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (1S,4S)-2-[1-Isocyano-meth-(Z)-ylidene]-1,7,7-trimethyl-bicyclo[2.2.1]heptane
  参考文献：
  名称：

  Multicomponent reactions. II. Stereoselective synthesis of 1(S)-camphor-2-cis-methylidene-isocyanide and its application in Passerini- and Ugi-reaction

  摘要：

  The use of unsaturated isocyanides in multicomponent reactions leads to N-vinylamides, which can be cleaved to carboxylic acids or esters under mild conditions. The chiral 1 (S)-camphor-2-cis-methylidene-isocyanide (5) can be prepared in two steps from camphor and methylisocyanide. Its application in the Passerini reaction generates alpha-acyloxyamides (6, 7, 8, 9) with a diastereomeric excess of > 92%, in the Ugi reaction alpha-acylaminoamides with a diastereomeric excess of 0% are formed.

  DOI：

  10.1002/prac.19973390167