((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-(2-phenyl-4,5-dihydro-oxazol-4-yl)-methanone | 852945-55-2

• 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,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-(2-phenyl-4,5-dihydro-oxazol-4-yl)-methanone
• 英文别名: [(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-(2-phenyl-4,5-dihydro-1,3-oxazol-4-yl)methanone；[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-(2-phenyl-4,5-dihydro-1,3-oxazol-4-yl)methanone
• CAS: 852945-55-2
• 化学式: C₂₀H₂₄N₂O₄S
• 分子量: 388.488
• InChiKey: FZFZNBVNZGBZFD-BZZYVRKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  84.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-(2-phenyl-4,5-dihydro-oxazol-4-yl)-methanone 、 溴甲苯 在 四丁基溴化铵 、 聚二(乙氧基吡咯烷酮)膦腈 、 lithium hydroxide 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 反应 0.25h， 以98%的产率得到2-phenyl-2-oxazoline-4-benzyl-4-carboxylic acid
  参考文献：
  名称：

  Enantioselective Synthetic Method for α-Alkylserine via Phase-Transfer Catalytic Alkylation of 2-Phenyl-2-oxazoline-4- carbonylcamphorsultam

  摘要：

  An enantioselective synthetic method for alpha-alkylserines by the phase-transfer catalytic alkylation of 2-phenyl-2-oxazo-line-4-carbonylcamphorsultam (4a) was developed. The phase-transfer catalytic alpha-alkylation of 4a using P2-Et at -78 degrees C gave alpha-alkylation (75 similar to 99%, 90 similar to 97% de), which could be easily hydrolyzed to alpha-alkylserines.

  DOI：

  10.1021/jo050197j
• 作为产物：
  描述：

  (2R)-bornane-10,2-sultam 、 methyl 2-phenyl-2-oxazoline-4-carboxylate 在 三甲基铝 作用下， 以 甲苯 为溶剂， 反应 30.0h， 以94%的产率得到((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-(2-phenyl-4,5-dihydro-oxazol-4-yl)-methanone
  参考文献：
  名称：

  Enantioselective Synthetic Method for α-Alkylserine via Phase-Transfer Catalytic Alkylation of 2-Phenyl-2-oxazoline-4- carbonylcamphorsultam

  摘要：

  An enantioselective synthetic method for alpha-alkylserines by the phase-transfer catalytic alkylation of 2-phenyl-2-oxazo-line-4-carbonylcamphorsultam (4a) was developed. The phase-transfer catalytic alpha-alkylation of 4a using P2-Et at -78 degrees C gave alpha-alkylation (75 similar to 99%, 90 similar to 97% de), which could be easily hydrolyzed to alpha-alkylserines.

  DOI：

  10.1021/jo050197j

文献信息

• Enantioselective Synthetic Method for α-Alkylserine via Phase-Transfer Catalytic Alkylation of 2-Phenyl-2-oxazoline-4- carbonylcamphorsultam
  作者：Jihye Lee、Yeon-Im Lee、Myoung Joo Kang、Yeon-Ju Lee、Byeong-Seon Jeong、Jeong-Hee Lee、Mi-Jeong Kim、Ji-yeon Choi、Jin-Mo Ku、Hyeung-geun Park、Sang-sup Jew

  DOI：10.1021/jo050197j

  日期：2005.5.1

  An enantioselective synthetic method for alpha-alkylserines by the phase-transfer catalytic alkylation of 2-phenyl-2-oxazo-line-4-carbonylcamphorsultam (4a) was developed. The phase-transfer catalytic alpha-alkylation of 4a using P2-Et at -78 degrees C gave alpha-alkylation (75 similar to 99%, 90 similar to 97% de), which could be easily hydrolyzed to alpha-alkylserines.