(4R,5R)-2-Ethyl-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid bis-[((R)-2-hydroxy-1-naphthalen-2-yl-ethyl)-amide] | 528840-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4R,5R)-2-Ethyl-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid bis-[((R)-2-hydroxy-1-naphthalen-2-yl-ethyl)-amide]
• CAS: 528840-94-0
• 化学式: C₃₂H₃₄N₂O₆
• 分子量: 542.632
• InChiKey: SBWSDJHUVVWMCK-QUAHOIDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  117.12
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R,5R)-2-Ethyl-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid bis-[((R)-2-hydroxy-1-naphthalen-2-yl-ethyl)-amide] 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (4R)-2-[(4R,5R)-2-ethyl-2-methyl-5-[(4R)-4-naphthalen-2-yl-4,5-dihydro-1,3-oxazol-2-yl]-1,3-dioxolan-4-yl]-4-naphthalen-2-yl-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Enantioselective Mercuriocyclization of γ-Hydroxy-cis-alkenes

  摘要：

  Asymmetric mercuriocyclization of gamma-hydroxy-(Z)-alkenes has been achieved using Hg(II) complexed with tartrate-derived 4-(2-naphthyl)bisoxazoline as chiral ligand to give rise to 2-monosubstituted tetrahydrofurans in 86-95% ee. Not only the linker connecting two oxazolines but also their 4-substituents were found crucial for high enantioselectivity. In addition, tuning the ketal protecting group of tartrate as well as adding MeOH and K(2)CO(3) worked beneficially.

  DOI：

  10.1021/ja029777d
• 作为产物：
  描述：

  O,O'-sec-butylidene-L_g-tartaric acid dimethyl ester 、 (R)-2-amino-2-(2-naphthyl)ethanol 在 potassium cyanide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以78%的产率得到(4R,5R)-2-Ethyl-2-methyl-[1,3]dioxolane-4,5-dicarboxylic acid bis-[((R)-2-hydroxy-1-naphthalen-2-yl-ethyl)-amide]
  参考文献：
  名称：

  Enantioselective Mercuriocyclization of γ-Hydroxy-cis-alkenes

  摘要：

  Asymmetric mercuriocyclization of gamma-hydroxy-(Z)-alkenes has been achieved using Hg(II) complexed with tartrate-derived 4-(2-naphthyl)bisoxazoline as chiral ligand to give rise to 2-monosubstituted tetrahydrofurans in 86-95% ee. Not only the linker connecting two oxazolines but also their 4-substituents were found crucial for high enantioselectivity. In addition, tuning the ketal protecting group of tartrate as well as adding MeOH and K(2)CO(3) worked beneficially.

  DOI：

  10.1021/ja029777d