trans-4-(hydroxymethyl)-5-methyl-3-phenyl-2-isoxazoline

• 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: trans-4-(hydroxymethyl)-5-methyl-3-phenyl-2-isoxazoline
• 英文别名: trans-4-hydroxymethyl-4-methyl-3-phenyl-4,5-dihydroisoxazole；[(4R,5R)-5-methyl-3-phenyl-4,5-dihydro-1,2-oxazol-4-yl]methanol
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: QWFAETMJOJOHMV-PSASIEDQSA-N

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

• 作为产物：
  描述：

  苯甲腈 N-氧化物 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 50.0h， 生成 trans-4-(hydroxymethyl)-5-methyl-3-phenyl-2-isoxazoline
  参考文献：
  名称：

  氧化腈与α，β-不饱和醛的环加成反应。确定区域化学作用的边际轨道相互作用和次要轨道相互作用

  摘要：

  已经确定了腈氧化物与巴豆醛和肉桂醛的环加成物的区域化学，并且也由边界轨道相互作用和次级轨道相互作用决定。在α，β-不饱和化合物的环加成反应中，前沿轨道相互作用的定向效应可通过空间漂移和次级轨道相互作用来转移。

  DOI：

  10.1016/s0040-4020(00)00356-2

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。
• Asymmetric 1,3-Dipolar Cycloaddition of Nitrile Oxides to γ-Substituted Allylic Alcohols
  作者：Yayoi Yoshida、Yutaka Ukaji、Shuhei Fujinami、Katsuhiko Inomata

  DOI：10.1246/cl.1998.1023

  日期：1998.10

  The asymmetric 1,3-dipolar cycloaddition of nitrile oxides to γ-substituted allylic alcohols was achieved by the use of diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding ...

  通过使用 (R,R)-酒石酸二异丙酯作为手性助剂，实现腈氧化物与 γ-取代烯丙醇的不对称 1,3-偶极环加成反应，得到相应的...
• Lanthanide triflate-catalyzed 1,3-dipolar cycloaddition reactions of polymer-supported nitrones with alkenes for the preparation of diverse 2-isoxazoline derivatives
  作者：Shū Kobayashi、Ryo Akiyama

  DOI：10.1016/s0040-4039(98)02100-5

  日期：1998.12

  1,3-Dipolar cycloaddition reactions of polymer-supported nitrones with alkenes proceeded smoothly in the presence of a catalytic amount of a lanthanide triflate to afford the corresponding 2-isoxazolines in high yields. Diverse 2-isoxazoline derivatives were prepared based on these solid-phase reactions.

  在催化量的三氟甲烷磺酸镧系元素的存在下，聚合物负载的硝基化合物与烯烃的1,3-偶极环加成反应平稳进行，从而以高收率提供了相应的2-异恶唑啉。基于这些固相反应制备了不同的2-异恶唑啉衍生物。
• First Successful Metal Coordination Control in 1,3-Dipolar Cycloadditions. High-Rate Acceleration and Regio- and Stereocontrol of Nitrile Oxide Cycloadditions to the Magnesium Alkoxides of Allylic and Homoallylic Alcohols
  作者：Shuji Kanemasa、Masaki Nishiuchi、Akio Kamimura、Kenzi Hori

  DOI：10.1021/ja00085a012

  日期：1994.3

  The first successful control of stereo- and regioselectivity in 1,3-dipolar cycloadditions by metal coordination is described. The presence of magnesium ions dramatically accelerates nitrile oxide dipolar cycloadditions to allylic alcohols, improving both the regio- and stereoselectivity of the reaction. For example, cycloadditions to terminal allylic alcohols bearing alpha-chirality produce syn-stereoisomers of 2-isoxazolines selectively, and reactions involving the magnesium alkoxides of internal allylic alcohols are exclusively regioselective in favor of 5-hydroxymethyl-2-isoxazolines. Metal alkoxides other than magnesium, such as lithium, zinc, and aluminum alkoxides, are less effective. These reactions involve the formation of activated intermediates in which a nitrile oxide and an allylic alkoxide coordinate to the magnesium ion. Theoretical calculations indicate that the formation of the coordinated intermediates enhances the rate of cycloaddition and also improves the syn-selectivity.
• Kim, Byeang Hyean, Synthetic Communications, 1987, vol. 17, # 10, p. 1199 - 1206
  作者：Kim, Byeang Hyean

  DOI：——

  日期：——