ethyl (2R)-2-(2-oxochromen-4-yl)oxypropanoate | 205645-27-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: ethyl (2R)-2-(2-oxochromen-4-yl)oxypropanoate
• CAS: 205645-27-8
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: VUVAYYSXHCBGGD-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (2R)-2-(2-oxochromen-4-yl)oxypropanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以81%的产率得到(R)-2-(2-Oxo-2H-chromen-4-yloxy)-propionic acid
  参考文献：
  名称：

  Coumarin-containing Amino Acids and Oxy Acids as Chiral Discriminating Agents. Part III. Novel Crystalline (R)-(+)- and (S)-(-)-O-Coumarinyl Lactic Acids as Chiral Derivatizing Agents for 1H NMR Inspection of Optical Purities of Alcohols and Amines

  摘要：

  Commercially available (S)-(-)-ethyl lactate and (R)-(+)methyl lactate were quits simply coupled with commercial 4-hydroxycoumarin by the Mitsunobu reaction followed by alkaline hydrolysis to furnish new crystalline optically pure (R)-(+)- and (S)-(-)-O-coumarinyllactic acids[RCLOH and SCLOH] in good yields. Diastereomeric esters and amides derived easily and quantitatively from these acids were subjected to chiral shift H-1 NRR examination revealing that these were efficient and reliable chiral derivatizing agents. Either racemization or kinetic resolution was not induced during derivatization.

  DOI：

  10.3987/com-97-s72
• 作为产物：
  描述：

  4-羟基香豆素 、 L(-)-乳酸乙酯 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以77%的产率得到ethyl (2R)-2-(2-oxochromen-4-yl)oxypropanoate
  参考文献：
  名称：

  Coumarin-containing Amino Acids and Oxy Acids as Chiral Discriminating Agents. Part III. Novel Crystalline (R)-(+)- and (S)-(-)-O-Coumarinyl Lactic Acids as Chiral Derivatizing Agents for 1H NMR Inspection of Optical Purities of Alcohols and Amines

  摘要：

  Commercially available (S)-(-)-ethyl lactate and (R)-(+)methyl lactate were quits simply coupled with commercial 4-hydroxycoumarin by the Mitsunobu reaction followed by alkaline hydrolysis to furnish new crystalline optically pure (R)-(+)- and (S)-(-)-O-coumarinyllactic acids[RCLOH and SCLOH] in good yields. Diastereomeric esters and amides derived easily and quantitatively from these acids were subjected to chiral shift H-1 NRR examination revealing that these were efficient and reliable chiral derivatizing agents. Either racemization or kinetic resolution was not induced during derivatization.

  DOI：

  10.3987/com-97-s72

文献信息

• Coumarin-containing Amino Acids and Oxy Acids as Chiral Discriminating Agents. Part III. Novel Crystalline (R)-(+)- and (S)-(-)-O-Coumarinyl Lactic Acids as Chiral Derivatizing Agents for 1H NMR Inspection of Optical Purities of Alcohols and Amines
  作者：Kazuo Nagasawa、Noriko Seto、Keiichi Ito

  DOI：10.3987/com-97-s72

  日期：——

  Commercially available (S)-(-)-ethyl lactate and (R)-(+)methyl lactate were quits simply coupled with commercial 4-hydroxycoumarin by the Mitsunobu reaction followed by alkaline hydrolysis to furnish new crystalline optically pure (R)-(+)- and (S)-(-)-O-coumarinyllactic acids[RCLOH and SCLOH] in good yields. Diastereomeric esters and amides derived easily and quantitatively from these acids were subjected to chiral shift H-1 NRR examination revealing that these were efficient and reliable chiral derivatizing agents. Either racemization or kinetic resolution was not induced during derivatization.