(S)-4-benzyl-3-(2-chloroacetyl)-5,5-diphenyloxazolidin-2-one | 1361955-40-9

• 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: (S)-4-benzyl-3-(2-chloroacetyl)-5,5-diphenyloxazolidin-2-one
• CAS: 1361955-40-9
• 化学式: C₂₄H₂₀ClNO₃
• 分子量: 405.881
• InChiKey: PAZMBMXZQGWISL-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-(2-chloroacetyl)-5,5-diphenyloxazolidin-2-one 在 copper(II) bis(trifluoromethanesulfonate) 、 sulfur 、 三乙胺 、 2,2′-亚甲基双[(4R,5S)-4,5-二苯基-2-噁唑啉] 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 17.5h， 生成 (4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-5,5-diphenyl-2-oxazolidinone 、 (4S)-3-[(4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyranyl)carbonyl]-4-benzyl-5,5-diphenyl-2-oxazolidinone
  参考文献：
  名称：

  Asymmetric diastereoselective thia-hetero-Diels–Alder reactions of dithioesters

  摘要：

  Asymmetric thia-Diels-Alder reactions involving new dithioesters bearing a chiral auxiliary are described, with diastereoselectivities up to 78%. Double-stereodifferentiating experiments employing chiral substrates in the presence of a chiral Lewis acid catalyst have been also carried out and, in this case, a diastereomeric excess of 90% was reached. The absolute stereochemistry of cycloadducts resulting from dithiooxalates and carbonyloxazolidinone dithioesters was assigned based on an X-ray structure and chemical correlation. In order to rationalize the sense of the chiral induction, stereochemical models for Cu(II)/bis(oxazoline)/dithioester complexes are proposed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.039
• 作为产物：
  描述：

  氯乙酰氯 、 (4S)-4-苄基-5,5-二苯基-2-恶唑烷酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到(S)-4-benzyl-3-(2-chloroacetyl)-5,5-diphenyloxazolidin-2-one
  参考文献：
  名称：

  Asymmetric diastereoselective thia-hetero-Diels–Alder reactions of dithioesters

  摘要：

  Asymmetric thia-Diels-Alder reactions involving new dithioesters bearing a chiral auxiliary are described, with diastereoselectivities up to 78%. Double-stereodifferentiating experiments employing chiral substrates in the presence of a chiral Lewis acid catalyst have been also carried out and, in this case, a diastereomeric excess of 90% was reached. The absolute stereochemistry of cycloadducts resulting from dithiooxalates and carbonyloxazolidinone dithioesters was assigned based on an X-ray structure and chemical correlation. In order to rationalize the sense of the chiral induction, stereochemical models for Cu(II)/bis(oxazoline)/dithioester complexes are proposed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.039