erythro/threo-α-methyl-3-phenyl-2-isoxazoline-5-methanol | 2126-01-4

• 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: erythro/threo-α-methyl-3-phenyl-2-isoxazoline-5-methanol
• 英文别名: 5-(1-hydroxyethyl)-3-phenyl-2-isoxazoline；1-(3-phenyl-4,5-dihydro-isoxazol-5-yl)-ethanol；5-(1-Hydroxy-ethyl)-3-phenyl-Δ²-isoxazolin；1-(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)ethanol
• CAS: 2126-01-4
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: QKHZHBZGPDGOAG-UHFFFAOYSA-N

物化性质

• 熔点：
  69.5 °C
• 沸点：
  309.4±34.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 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：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  erythro/threo-α-methyl-3-phenyl-2-isoxazoline-5-methanol 在 氢氟酸 、 lithium diisopropyl amide 作用下， 生成 1-(4-Methyl-3-phenyl-4,5-dihydro-isoxazol-5-yl)-ethanol
  参考文献：
  名称：

  Nucleophilic additions to and reductiosn of 5-formyl-and 5-acyl-2-isoxazolines (4,5-dihydeoisoxazoles): a stereoselective route to β,γ-dihydroxy ketones

  摘要：

  Reductions of readily available 5-acyl-2-isoxazolines with L-Selectride follow the Felkin-Anh model and produce syn-5-hydroxyalkyl-2-isoxazolines with excellent (> 95:5) selectivities. Swern oxidation of 5-hydroxymethyl-2-isoxazolines, followed by direct addition of a Grignard reagent to the intermediate 5-formyl-2-isoxazolines, also follows the Felkin-Anh model and produces anti-5-hydroxyalkyl-2-isoxazolines with modest (80:20) to excellent (> 95:5) selectivity. In contrast, additions of Grignard reagents to 5-acyl-2-isoxazolines follow the chelation model, and give syn or anti products (depending on choice of acyl substituent and Grignard reagent) with good (90:10) to excellent selectivity. These selectivities are almost always far superior to those that can be obtained by direct nitrile oxide cycloaddition to a chiral allylic alcohol or ether. The resulting products are readily reduced to syn- or anti-beta,gamma-dihydroxy ketones. A speculative model to explain this surprising reversal in selectivity between formyl and acyl isoxazolines is proposed.

  DOI：

  10.1039/p19910002613
• 作为产物：
  描述：

  5-acetyl-4,5-dihydro-3-phenylisoxazole 在 potassium tri-sec-butyl-borohydride 、 氢氧化钾 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到erythro/threo-α-methyl-3-phenyl-2-isoxazoline-5-methanol
  参考文献：
  名称：

  2-Isoxazolines with an electron-acceptor substituent at C(5) in reactions with nucleophilic reagents

  摘要：

  DOI：

  10.1007/s10593-007-0053-6

文献信息

• Microwave Accelerated Cycloaddition Reactions of Nitrile Oxides and Allylic Alcohols
  作者：Ta-Jung Lu、Gwo-Ming Tzeng

  DOI：10.1002/jccs.200000022

  日期：2000.2

  promoting the cycloaddition reactions of allyl alcohols with nitrile oxides using a domestic microwave oven and a focused monomode microwave reactor have demonstrated that not only was the reaction time substantially reduced, but also the reaction yields were significantly improved over the conventional stirred reactions. Microwave irradiation alters the regioselectivity of the cycloaddition reaction which

  使用家用微波炉和聚焦单模微波反应器应用微波促进烯丙醇与氧化腈的环加成反应表明，与传统的搅拌反应器相比，不仅反应时间显着缩短，而且反应收率显着提高反应。微波照射改变了环加成反应的区域选择性，这有利于非氢键导向的环加合物异恶唑啉 4。
• A strategic alternative to solid phase synthesis: Preparation of a small isoxazoline library by “fluorous synthesis”
  作者：Armido Studer、Dennis P. Curran

  DOI：10.1016/s0040-4020(97)00224-x

  日期：1997.5

  The preparation of a highly fluorinated silyl group and its use as a ''fluorous label'' are described. Allyl and propargyl alcohols are rendered fluorous upon attachment to the fluorous label. Cycloaddition of the fluorous dipolarophiles to nitrite oxides provides the corresponding isoxazol(in)es which are purified by simple liquid-liquid extractions. After detachment of the label and renewed extraction, the organic isoxazol(in)es are obtained. This new fluorous methodology allows the preparation of isoxazol(in)es in high purities without using chromatography. (C) 1997 Elsevier Science Ltd.
• NAKATA, TADASHI;TANI, YOICHIRO;HATOZAKI, MASAYOSHI;OISHI, TAKESHI, J. AMER. CHEM. SOC., 1984, 106, N 13, 3880-3882
  作者：NAKATA, TADASHI、TANI, YOICHIRO、HATOZAKI, MASAYOSHI、OISHI, TAKESHI

  DOI：——

  日期：——
• FLUOROUS REACTION AND SEPARATION SYSTEMS
  申请人：UNIVERSITY OF PITTSBURGH

  公开号：EP0907625A1

  公开（公告）日：1999-04-14
• EP0907625A4
  申请人：——

  公开号：EP0907625A4

  公开（公告）日：2004-10-20