(R)-(4-ethyl)-2-phenyloxazoline | 156428-99-8

• 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: (R)-(4-ethyl)-2-phenyloxazoline
• 英文别名: 4-R-(-)-ethyl-2-phenyloxazoline；(R)-2-phenyl-4-ethyl-oxazoline；(R)-4-Ethyl-2-phenyl-4,5-dihydrooxazole；(4R)-4-ethyl-2-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 156428-99-8
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: KWCYSQDVFQGKSA-SNVBAGLBSA-N

物化性质

• 沸点：
  276.4±9.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(4-ethyl)-2-phenyloxazoline 在 selenium 、 正丁基锂 、 碘 、 氧气 、 碳酸氢钠 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 生成 (R)-(-)-<2-(4-ethyl-2-oxazolinyl)phenyl>selenyl iodide
  参考文献：
  名称：

  Novel chiral organoselenenyl halides stabilized by Se···N nonbonded interactions: synthesis and structural characterization

  摘要：

  The first examples of structurally characterized chiral organoselenenyl halides stabilized by Se ... N intramolecular interactions are described. The existence of strong nonbonded Se ... N interactions in the solid state as well as in solution was unambiguously determined by single-crystal X-ray analysis and Se-77 NMR spectroscopy. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00507-2
• 作为产物：
  描述：

  2-氨基丁醇 、 苯甲亚胺酸乙酯盐酸盐 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以80%的产率得到(R)-(4-ethyl)-2-phenyloxazoline
  参考文献：
  名称：

  Novel chiral organoselenenyl halides stabilized by Se···N nonbonded interactions: synthesis and structural characterization

  摘要：

  The first examples of structurally characterized chiral organoselenenyl halides stabilized by Se ... N intramolecular interactions are described. The existence of strong nonbonded Se ... N interactions in the solid state as well as in solution was unambiguously determined by single-crystal X-ray analysis and Se-77 NMR spectroscopy. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00507-2

文献信息

• β-Amidoaldehydes via oxazoline hydroformylation
  作者：David S. Laitar、John W. Kramer、Bryan T. Whiting、Emil B. Lobkovsky、Geoffrey W. Coates

  DOI：10.1039/b913698c

  日期：——

  4-Substituted oxazolines, which are readily synthesized from naturally occurring α-amino acids, are converted efficiently and stereospecifically to β-amidoaldehydes in the presence of synthesis gas and catalytic dicobalt octacarbonyl.

  易于从天然存在的α-氨基酸合成得到的4-取代噁唑啉，在合成气（CO和H2）及催化剂二钴八羰基的存在下，能够高效且立体专一性地转化为β-氨基醛。
• Glutathione Peroxidase-like Antioxidant Activity of Diaryl Diselenides:  A Mechanistic Study
  作者：G. Mugesh、Arunashree Panda、Harkesh B. Singh、Narayan S. Punekar、Ray J. Butcher

  DOI：10.1021/ja994467p

  日期：2001.2.1

  nucleophilic attack of thiol takes place preferentially at selenium rather than sulfur and this reduces the formation of selenol by terminating the forward reaction. On the other hand, the diselenides having weak Se.N interactions are found to be more active due to the fast reaction of the selenenyl sulfide derivatives with thiol to produce diphenyl disulfide and the expected selenol (RSeSR + PhSH = PhSSPh

  描述了几种具有分子内配位氨基的二芳基二硒化物的合成、结构和硫醇过氧化物酶样抗氧化活性。源自对映体纯 R-(+)- 和 S-(-)-N,N-二甲基（1-二茂铁基乙基）胺的二硒化物显示出优异的过氧化物酶活性。为了研究各种有机硒中间体的机械作用，通过 (77)Se NMR 光谱对中间体进行了详细的原位表征。虽然大多数二硒化物通过硒醇、硒酸和硒基硫化物中间体发挥其过氧化物酶活性，但二硒化物相对活性的差异是由于分子内硒相互作用的程度不同。二硒化物具有强硒。由于其硒基硫化物衍生物能够增强反向 GPx 循环（RSeSR + H(2)O(2) = RSeOH），N 相互作用被发现处于非活动状态。在这些情况下，硫醇的亲核攻击优先发生在硒而不是硫上，这通过终止正向反应来减少硒醇的形成。另一方面，由于硒基硫化物衍生物与硫醇快速反应生成二苯基二硫化物和预期的硒醇（RSeSR + PhSH = PhSSPh + RSeH），因此发现具有弱
• N-Heterocyclic carbene (NHC) palladium(II) complexes bearing chiral oxazoline ligands and their catalytic activities in allylic alkylation reactions
  作者：Serpil DENİZALTI、Hayati TÜRKMEN、Bekir ÇETİNKAYA

  DOI：10.3906/kim-1312-60

  日期：——

  NHC--Pd(II) complexes bearing a chiral oxazoline ligand (IIIa--f) were synthesized by cleavage of dimeric palladium complexes with the oxazoline ligand. They were fully characterized by ^1H and ^13}C NMR and elemental analyses. The catalytic activity of the complexes (IIIa--f) in allylic alkylation reactions was evaluated. The complex IIIa was found to be the most active catalyst. Very low ee values indicate that the oxazoline is dissociated from the active catalytic species.

  通过二聚钯配合物与噁唑啉配体的裂解，合成了NHC-Pd(II)配合物（IIIa-f）。通过^1H和^13}C NMR以及元素分析对其进行了全面表征。评估了配合物（IIIa-f）在烯丙基烷基化反应中的催化活性。发现配合物IIIa是最活跃的催化剂。极低的ee值表明噁唑啉从活性催化物种中解离。
• IMMUNOMODULATORY COMPOUNDS AND METHODS OF USE THEREOF
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP1511499B1

  公开（公告）日：2008-12-03
• COMPOUNDS FOR PREPARING IMMUNOLOGICAL ADJUVANT
  申请人：Eisai R&D Management Co., Ltd.

  公开号：US20140012011A1

  公开（公告）日：2014-01-09

  The present invention provides methods for preparing TLR-4 receptor agonist E6020: and stereoisomers thereof, which compounds are useful as an immunological adjuvants when co-administered with antigens such as vaccines for bacterial and viral diseases. Also provided are synthetic intermediates.