1-((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonyl)-1H-imidazole-4-carbaldehyde | 134553-19-8

• 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: 1-((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonyl)-1H-imidazole-4-carbaldehyde
• CAS: 134553-19-8
• 化学式: C₁₄H₁₈N₂O₄S
• 分子量: 310.374
• InChiKey: UIXODPKOAHNVRJ-QMTHXVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  86.1
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonyl)-1H-imidazole-4-carbaldehyde 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (1S,4R)-1-{4-[1-(tert-Butyl-diphenyl-silanyloxy)-allyl]-imidazole-1-sulfonylmethyl}-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  Synthèse stéréosélective de la girolline

  摘要：

  Desaminogirollines syn 2'S,3'S and 2'R,3'R have been prepared from N1-camphosulfonamide 4-carboxaldehyde imidazole and their diastereoisomeric derivatives have been separated. The stereoselective synthesis of chiral natural girolline has been achieved from D(-)arabinose: this ose is condensed with formamidine acetate to obtain a 4(5)-[1',2',3'-trihydroxypropyl]-imidazole; the side-chain is chlorinated before being aminated via an azido compound and the 2-amino group of girolline is obtained by rhodium catalytic reduction of the 2-diazo derivative.

  DOI：

  10.1016/s0040-4020(01)80443-9
• 作为产物：
  描述：

  右旋樟脑-10-磺酰氯 、 4-咪唑甲醛 在 potassium tert-butylate 作用下， 生成 1-((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-ylmethanesulfonyl)-1H-imidazole-4-carbaldehyde
  参考文献：
  名称：

  Synthèse stéréosélective de la girolline

  摘要：

  Desaminogirollines syn 2'S,3'S and 2'R,3'R have been prepared from N1-camphosulfonamide 4-carboxaldehyde imidazole and their diastereoisomeric derivatives have been separated. The stereoselective synthesis of chiral natural girolline has been achieved from D(-)arabinose: this ose is condensed with formamidine acetate to obtain a 4(5)-[1',2',3'-trihydroxypropyl]-imidazole; the side-chain is chlorinated before being aminated via an azido compound and the 2-amino group of girolline is obtained by rhodium catalytic reduction of the 2-diazo derivative.

  DOI：

  10.1016/s0040-4020(01)80443-9