(1S,2S,5'S)-N,N-diisopropyl [2-spiro-2'-(5'-phenyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide | 256393-11-0

• 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,2S,5'S)-N,N-diisopropyl [2-spiro-2'-(5'-phenyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide
• 英文别名: (1R,2S,5'S)-N,N-diisopropyl-[2-spiro-2'-(5'-phenyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide；1-[(1'S,2S,4'R,5S)-7',7'-dimethyl-4-oxo-5-phenylspiro[1,3-dioxolane-2,2'-bicyclo[2.2.1]heptane]-1'-yl]-N,N-di(propan-2-yl)methanesulfonamide
• CAS: 256393-11-0
• 化学式: C₂₄H₃₅NO₅S
• 分子量: 449.612
• InChiKey: KMAQYMBWCGZPDH-SHBJFUFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,5'S)-N,N-diisopropyl [2-spiro-2'-(5'-phenyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 5.5h， 生成 (2S)-2-hydroxy-2-phenyl-4-pentenoic acid
  参考文献：
  名称：

  Enantioselective Synthesis of α-Hydroxy Acids Employing (1S)-(+)-N,N-Diisopropyl-10-camphorsulfonamide as Chiral Auxiliary

  摘要：

  [GRAPHICS]Lewis acid (BF3. OEt2) catalyzed condensation of dimethoxy acetal 2 with alpha-hydroxy acids produces chiral 1,3-dioxolanones I. The enolates derived from these compounds undergo reactions with alkyl halides with a high level of diastereoselectivity. Subsequent hydrolysis of these alkylated products II gives mono- and disubstituted alpha-hydroxy acids III with high enantiomeric excesses.

  DOI：

  10.1021/ol9910666
• 作为产物：
  描述：

  (1S)-N,N-diisopropyl (2,2-dimethoxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonamide 、 扁桃酸 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 以56%的产率得到(1S,2S,5'S)-N,N-diisopropyl [2-spiro-2'-(5'-phenyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide
  参考文献：
  名称：

  Enantioselective Synthesis of α-Hydroxy Acids Employing (1S)-(+)-N,N-Diisopropyl-10-camphorsulfonamide as Chiral Auxiliary

  摘要：

  [GRAPHICS]Lewis acid (BF3. OEt2) catalyzed condensation of dimethoxy acetal 2 with alpha-hydroxy acids produces chiral 1,3-dioxolanones I. The enolates derived from these compounds undergo reactions with alkyl halides with a high level of diastereoselectivity. Subsequent hydrolysis of these alkylated products II gives mono- and disubstituted alpha-hydroxy acids III with high enantiomeric excesses.

  DOI：

  10.1021/ol9910666

文献信息

• Enantioselective Synthesis of <i>α</i>-Hydroxy Acids Employing (1<i>S</i>)-(+)-<i>N</i>,<i>N</i>-Diisopropyl-10-camphorsulfonamide as Chiral Auxiliary
  作者：Jia-Wen Chang、Der-Pin Jang、Biing-Jiun Uang、Fen-Ling Liao、Sue-Lein Wang

  DOI：10.1021/ol9910666

  日期：1999.12.1

  [GRAPHICS]Lewis acid (BF3. OEt2) catalyzed condensation of dimethoxy acetal 2 with alpha-hydroxy acids produces chiral 1,3-dioxolanones I. The enolates derived from these compounds undergo reactions with alkyl halides with a high level of diastereoselectivity. Subsequent hydrolysis of these alkylated products II gives mono- and disubstituted alpha-hydroxy acids III with high enantiomeric excesses.