(4S)-2-(3,3-diphenyloxiran-2-yl)-4-isopropyl-4,5-dihydrooxazole | 1219440-90-0

• 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: (4S)-2-(3,3-diphenyloxiran-2-yl)-4-isopropyl-4,5-dihydrooxazole
• CAS: 1219440-90-0
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: XLHULWGLELEYFU-QNSVNVJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  34.12
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(p-tolylsulfinyl)benzaldehyde 、 (4S)-2-(3,3-diphenyloxiran-2-yl)-4-isopropyl-4,5-dihydrooxazole 在 四甲基乙二胺 、 仲丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 0.75h， 以27%的产率得到[1S,2R,S(S)]-[2-(4S)-isopropyl-4,5-dihydrooxazol-2-yl-3,3-diphenyloxiran-2-yl]-[2-(p-tolylsulfinyl)phenyl]methanol
  参考文献：
  名称：

  Stereoselective synthesis of 2,3-epoxy alcohols mediated by a remote sulfinyl group

  摘要：

  The influence of the sulfinyl group as a chiral auxiliary in the stereoselective addition of oxiranyllithiums to (S)(S)-2-p-tolylsulfinylbenzaldehyde has been studied. All reactions evolve with retention of configuration at the starting lithiated carbon. Completely stereoselective additions have been observed when configurations at sulfur and the lithiated carbon are different (matched pair), whereas variable dr's values (ranging between 52:48 and >99:<1%) when they are identical (mismatched pair). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.12.006

文献信息

• Stereoselective synthesis of 2,3-epoxy alcohols mediated by a remote sulfinyl group
  作者：José Luis García Ruano、Ana M. Martín-Castro、Francisco Tato、Esther Torrente、M. Giovanna Tocco、Saverio Florio、Vito Capriati

  DOI：10.1016/j.tet.2009.12.006

  日期：2010.2

  The influence of the sulfinyl group as a chiral auxiliary in the stereoselective addition of oxiranyllithiums to (S)(S)-2-p-tolylsulfinylbenzaldehyde has been studied. All reactions evolve with retention of configuration at the starting lithiated carbon. Completely stereoselective additions have been observed when configurations at sulfur and the lithiated carbon are different (matched pair), whereas variable dr's values (ranging between 52:48 and >99:<1%) when they are identical (mismatched pair). (C) 2009 Elsevier Ltd. All rights reserved.