(4R)-3,3-dichloro-4-[(1S)-1-phenylmethoxyethyl]oxetan-2-one | 211573-12-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R)-3,3-dichloro-4-[(1S)-1-phenylmethoxyethyl]oxetan-2-one
• CAS: 211573-12-5
• 化学式: C₁₂H₁₂Cl₂O₃
• 分子量: 275.131
• InChiKey: MELYTKIJKNEWJI-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-3,3-dichloro-4-[(1S)-1-phenylmethoxyethyl]oxetan-2-one 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到(4R,5S)-3,3-Dichloro-4-hydroxy-5-methyl-dihydro-furan-2-one
  参考文献：
  名称：

  Origins of Stereocontrol in the [2 + 2] Cycloaddition between Achiral Ketenes and Chiral α-Alkoxy Aldehydes. A Pericyclic Alternative to the Aldol Reaction

  摘要：

  Ab Initio calculations predict that the thermal [2 + 2] cycloaddition reaction between C(2 upsilon)-symmetric ketenes and enantiopure aldehydes takes place with high enough stereocontrol for preparative purposes. The sense of induction is predicted to be non-Felkin. It is also found that the [2 + 2] cycloaddition involving nonactivated ketenes is facilitated by using 5 M solutions of lithium perchlorate in diethyl ether. It is found that both the purely thermal and lithium-assisted [2 + 2] cycloadditions result in the same type of stereocontrol. This method constitutes a general route for the synthesis of homochiral 2-oxetanones and related compounds, thus providing a pericyclic alternative to the aldol reaction.

  DOI：

  10.1021/jo9806512
• 作为产物：
  描述：

  二氯乙酰氯 、 (S)-2-苄氧基丙醛 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以70%的产率得到(4R)-3,3-dichloro-4-[(1S)-1-phenylmethoxyethyl]oxetan-2-one
  参考文献：
  名称：

  Origins of Stereocontrol in the [2 + 2] Cycloaddition between Achiral Ketenes and Chiral α-Alkoxy Aldehydes. A Pericyclic Alternative to the Aldol Reaction

  摘要：

  Ab Initio calculations predict that the thermal [2 + 2] cycloaddition reaction between C(2 upsilon)-symmetric ketenes and enantiopure aldehydes takes place with high enough stereocontrol for preparative purposes. The sense of induction is predicted to be non-Felkin. It is also found that the [2 + 2] cycloaddition involving nonactivated ketenes is facilitated by using 5 M solutions of lithium perchlorate in diethyl ether. It is found that both the purely thermal and lithium-assisted [2 + 2] cycloadditions result in the same type of stereocontrol. This method constitutes a general route for the synthesis of homochiral 2-oxetanones and related compounds, thus providing a pericyclic alternative to the aldol reaction.

  DOI：

  10.1021/jo9806512

文献信息

• Origins of Stereocontrol in the [2 + 2] Cycloaddition between Achiral Ketenes and Chiral α-Alkoxy Aldehydes. A Pericyclic Alternative to the Aldol Reaction
  作者：Begoña Lecea、Ana Arrieta、Iosune Arrastia、Fernando P. Cossío

  DOI：10.1021/jo9806512

  日期：1998.7.1

  Ab Initio calculations predict that the thermal [2 + 2] cycloaddition reaction between C(2 upsilon)-symmetric ketenes and enantiopure aldehydes takes place with high enough stereocontrol for preparative purposes. The sense of induction is predicted to be non-Felkin. It is also found that the [2 + 2] cycloaddition involving nonactivated ketenes is facilitated by using 5 M solutions of lithium perchlorate in diethyl ether. It is found that both the purely thermal and lithium-assisted [2 + 2] cycloadditions result in the same type of stereocontrol. This method constitutes a general route for the synthesis of homochiral 2-oxetanones and related compounds, thus providing a pericyclic alternative to the aldol reaction.