(R_s, S_c)-4-phenyl-N-(2-chlorotetrafluoroethanesulfinyl)oxazolidin-2-one | 1262682-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R_s, S_c)-4-phenyl-N-(2-chlorotetrafluoroethanesulfinyl)oxazolidin-2-one
• 英文别名: (4S)-3-[(R)-(2-chloro-1,1,2,2-tetrafluoroethyl)sulfinyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 1262682-98-3
• 化学式: C₁₁H₈ClF₄NO₃S
• 分子量: 345.702
• InChiKey: BCKSFFLKKGZLQB-IJSAXESFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R_s, S_c)-4-phenyl-N-(2-chlorotetrafluoroethanesulfinyl)oxazolidin-2-one 在 lithium hexamethyldisilazane 、 水 、 氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以72%的产率得到(S)-2-chlorotetrafluoroethanesulfinamide
  参考文献：
  名称：

  Per(poly)fluoroalkanesulfinamides assisted diastereoselective three-component inverse-electron-demand aza Diels–Alder reaction

  摘要：

  报道了一种由全（多）氟烷基亚磺酰胺协助的高度立体选择性的三组分逆电子需求aza-Diels-Alder反应，提供了广泛的高度功能化的哌啶衍生物，具有优异的内型/外型和面立体选择性。吸电子的全氟烷基对于该反应在温和条件下的成功至关重要，并有助于监测反应过程和立体选择性。这些环加合物的合成潜力也得到了强调。

  DOI：

  10.1039/c0ob00699h
• 作为产物：
  描述：

  2-chloro-1,1,2,2-tetrafluoroethanesulfinyl chloride 、 (S)-4-苯基-2-恶唑烷酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 生成 (R_s, S_c)-4-phenyl-N-(2-chlorotetrafluoroethanesulfinyl)oxazolidin-2-one
  参考文献：
  名称：

  多氟烷烃亚磺酰胺诱导的酮的一锅不对称还原胺化

  摘要：

  使用手性2-氯-1,1,2,2-四氟乙烷-1-亚磺酰胺作为辅助剂，在硼氢化钠存在下，实现了用于酮的不对称还原胺化的有效一锅法。芳族酮和脂族酮均反应良好，以良好的收率和优异的非对映选择性，得到相应的亚磺酰基酰胺。

  DOI：

  10.1016/j.jfluchem.2015.01.019

文献信息

• Per(poly)fluoroalkanesulfinamides assisted diastereoselective three-component inverse-electron-demand aza Diels–Alder reaction
  作者：Peng Li、Li-Juan Liu、Jin-Tao Liu

  DOI：10.1039/c0ob00699h

  日期：——

  A highly diastereoselective three-component inverse-electron-demand aza Diels–Alder reaction assisted by per(poly)fluoro-alkanesulfinamides is presented, providing a broad spectrum of highly functionalized piperidine derivatives with excellent endo/exo and facial diastereoselectivities. The electron-withdrawing perfluoroalkyl groups are crucial for the success of this reaction under mild conditions and facilitate monitoring the process and stereoselectivities of the reaction. The synthetic potential of these cycloadducts is also highlighted.

  报道了一种由全（多）氟烷基亚磺酰胺协助的高度立体选择性的三组分逆电子需求aza-Diels-Alder反应，提供了广泛的高度功能化的哌啶衍生物，具有优异的内型/外型和面立体选择性。吸电子的全氟烷基对于该反应在温和条件下的成功至关重要，并有助于监测反应过程和立体选择性。这些环加合物的合成潜力也得到了强调。
• Optically Pure Polyfluoroalkanesulfinamides: Synthesis and Application as Promising and Monitorable Chiral Auxiliaries
  作者：Li-Juan Liu、Ling-Jun Chen、Peng Li、Xiao-Bo Li、Jin-Tao Liu

  DOI：10.1021/jo200119x

  日期：2011.6.3

  Efficient synthesis of enantiopure polyfluoroalkanesulfinamides (PFSAs) has been achieved. Their application as novel chiral auxiliaries with an electron-withdrawing and F-19 NMR monitorable polyfluoroalkyl group was initially demonstrated in an asymmetric Strecker reaction under mild conditions.
• The Synthesis and Strecker Reaction of 2-Chlorotetrafluoroethanesulfinyl Ketimines
  作者：Kai Yang、Li-Juan Liu、Jin-Tao Liu

  DOI：10.1021/jo500008e

  日期：2014.4.4

  A series of 2-chlorotetrafluoroethanesulfinyl ketimines were prepared from 2-chlorotetrafluoroethanesulfinamide and ketones in high yields, and their Strecker reactions with TMSCN have been investigated. High yields and excellent diastereoselectivities were achieved in the presence of a catalytic amount of CsF under mild conditions. The six-membered chairlike models were proposed to account for the high stereoselective Strecker reaction.
• One-pot asymmetric reductive amination of ketones induced by polyfluoroalkanesulfinamide
  作者：Kai Yang、Jin-Tao Liu

  DOI：10.1016/j.jfluchem.2015.01.019

  日期：2015.5

  Using chiral 2-chloro-1,1,2,2-tetrafluoroethane-1-sulfinamide as the auxiliary, an efficient one-pot procedure for the asymmetric reductive amination of ketones was achieved in the presence of sodium borohydride. Both aromatic and aliphatic ketones reacted well to give the corresponding sulfinyl amides in good yields with excellent diastereoselectivities.

  使用手性2-氯-1,1,2,2-四氟乙烷-1-亚磺酰胺作为辅助剂，在硼氢化钠存在下，实现了用于酮的不对称还原胺化的有效一锅法。芳族酮和脂族酮均反应良好，以良好的收率和优异的非对映选择性，得到相应的亚磺酰基酰胺。