(S)-4-benzyl-2-(thiophen-3-yl)-2-oxazoline | 374073-86-6

• 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-2-(thiophen-3-yl)-2-oxazoline
• 英文别名: Oxazoline 15；(4S)-4-benzyl-2-thiophen-3-yl-4,5-dihydro-1,3-oxazole
• CAS: 374073-86-6
• 化学式: C₁₄H₁₃NOS
• 分子量: 243.329
• InChiKey: HUHVJSXYULHZJW-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-2-(thiophen-3-yl)-2-oxazoline 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以38%的产率得到4-Benzyl-2-thiophen-3-yl-1,3-oxazole
  参考文献：
  名称：

  1,4-Disubstituted imidazoles are potential antibacterial agents functioning as inhibitors of enoyl acyl carrier protein reductase (FabI)

  摘要：

  1,4-Disubstituted imidazole inhibitors of Staphylococcus aureus and Escherichia coli enoyl acyl carrier protein reductase (FabI) have been identified. Crystal structure data shows the inhibitor 1 bound in the enzyme active site of E. coli FabI. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00404-8
• 作为产物：
  描述：

  L-苯丙氨醇 在 伯吉斯试剂 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-benzyl-2-(thiophen-3-yl)-2-oxazoline
  参考文献：
  名称：

  1,4-Disubstituted imidazoles are potential antibacterial agents functioning as inhibitors of enoyl acyl carrier protein reductase (FabI)

  摘要：

  1,4-Disubstituted imidazole inhibitors of Staphylococcus aureus and Escherichia coli enoyl acyl carrier protein reductase (FabI) have been identified. Crystal structure data shows the inhibitor 1 bound in the enzyme active site of E. coli FabI. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00404-8

文献信息

• Synthesis of modular thiophene-oxazoline ligands and their application in the asymmetric phenyl transfer reaction to aldehydes
  作者：Zhuo Chai、Xin-Yuan Liu、Xiao-Yu Wu、Gang Zhao

  DOI：10.1016/j.tetasy.2006.09.004

  日期：2006.9

  A series of thiophene mono (oxazoline) N,O-ligands with three sites of diversity were synthesized concisely in two steps from the corresponding thiophene carbonitriles. These ligands were applied to the enantioselective phenyl transfer reaction of aldehydes, resulting in the corresponding chiral diaryl methanol products with excellent yields and moderate to good enantioselectivities.

  从相应的噻吩腈中分两步简要合成了具有三个多样性位点的一系列噻吩单（恶唑啉）N，O-配体。将这些配体用于醛的对映选择性苯基转移反应，得到具有优异收率和中等至良好对映选择性的相应的手性二芳基甲醇产物。
• Secondary Phosphine Oxide Preligands for Palladium-Catalyzed C-H (Hetero)Arylations: Efficient Access to Pybox Ligands
  作者：Debasish Ghorai、Valentin Müller、Helena Keil、Dietmar Stalke、Giuseppe Zanoni、Boryslav A. Tkachenko、Peter R. Schreiner、Lutz Ackermann

  DOI：10.1002/adsc.201700663

  日期：2017.9.18

  C–H arylations of oxazolines were accomplished with a well‐defined palladium catalyst derived from a secondary bisdiamantyl phosphine oxide. The single‐component secondary phosphine oxide (SPO)‐palladium complex enabled C–H activations with aryl bromides and challenging aryl chlorides in the absence of directing groups, setting the stage for the step‐economical synthesis of pybox ligands under racemization‐free

  恶唑啉的C–H芳基化反应是使用衍生自仲双双金刚烷基氧化膦的明确定义的钯催化剂完成的。单组分仲氧化膦（SPO）-钯配合物可在没有引导基团的情况下用芳基溴化物和具有挑战性的芳基氯化物进行C-H活化，为在无消旋反应条件下逐步经济地合成pybox配体奠定了基础。