(5-methyl-3-phenyl-4,5-dihydroisoxazol-5-yl)methanol | 77790-76-2

• 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: (5-methyl-3-phenyl-4,5-dihydroisoxazol-5-yl)methanol
• 英文别名: 5-hydroxymethyl-5-methyl-3-phenyl-2-isoxazoline；(5-methyl-3-phenyl-4H-1,2-oxazol-5-yl)methanol
• CAS: 77790-76-2
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: BECAEFJGIOAKCY-UHFFFAOYSA-N

物化性质

• 熔点：
  60 °C
• 沸点：
  301.8±34.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：

  (5-methyl-3-phenyl-4,5-dihydroisoxazol-5-yl)methanol 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以97%的产率得到4-amino-2-methyl-4-phenylbutane-1,2-diol
  参考文献：
  名称：

  Palladium-Catalyzed Oxime Assisted Intramolecular Dioxygenation of Alkenes with 1 atm of Air as the Sole Oxidant

  摘要：

  This paper describes a palladium-catalyzed oxime assisted intramolecular dioxygenation of alkenes by using 1 atm of air as the sole oxidant under extremely mild conditions, which demonstrated the feasibility of incorporating atmospheric oxygen into synthetically useful products under 1 atm of air at room temperature.

  DOI：

  10.1021/ja100716x
• 作为产物：
  描述：

  4-甲基-5,6-二氢吡喃-2-酮 在 吡啶 、 N-碘代丁二酰亚胺 、 盐酸羟胺 、 potassium tert-butylate 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 环己烷 为溶剂， 反应 27.8h， 生成 (5-methyl-3-phenyl-4,5-dihydroisoxazol-5-yl)methanol
  参考文献：
  名称：

  Catalytic Enantioselective 1,4-Iodofunctionalizations of Conjugated Dienes

  摘要：

  The first catalytic enantioselective 1,4-iodofunctionalizations of conjugated dienes have been developed. Starting from beta,gamma,delta,epsilon-unsaturated oximes and 4-Ns hydrazones, these N-iodosuccinimide-mediated reactions are catalyzed by newly modified tertiary aminothiourea derivatives and furnish Delta(2)-isoxazoline and Delta(2)-pyrazoline derivatives, respectively, containing an (E)-allyl iodide group at the quaternary stereogenic center generally in high yield and with excellent enantioselectivity (up to 98.5:1.5 er).

  DOI：

  10.1021/acs.orglett.5b02026

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。
• Photo-organocatalytic synthesis of acetals from aldehydes
  作者：Nikolaos F. Nikitas、Ierasia Triandafillidi、Christoforos G. Kokotos

  DOI：10.1039/c8gc03605e

  日期：——

  developed. Utilizing thioxanthenone as the photocatalyst and inexpensive household lamps as the light source, a variety of aromatic and aliphatic aldehydes have been converted into acyclic and cyclic acetals in high yields. The reaction mechanism was extensively studied.

  已经开发出用于醛的高效缩醛化的温和绿色光有机催化方案。利用噻吨酮作为光催化剂，使用廉价的家用灯作为光源，已将各种芳族和脂族醛高产率地转化为无环和环状缩醛。反应机理得到了广泛的研究。
• Green Organocatalytic Synthesis of Isoxazolines via a One-Pot Oxidation of Allyloximes
  作者：Ierasia Triandafillidi、Christoforos G. Kokotos

  DOI：10.1021/acs.orglett.6b03380

  日期：2017.1.6

  A green, sustainable, organocatalytic, and efficient synthesis of isoxazolines from allyloximes was developed. A 2,2,2-trifluoroacetophenone-catalyzed oxidation of allyloximes, utilizing H2O2 as the green oxidant, was taken advantage of in order to introduce a cheap and environmentally friendly protocol for the synthesis of substituted isoxazolines. A variety of substitution patterns, both aromatic

  从烯丙基肟开发了一种绿色，可持续，有机催化和高效的异恶唑啉合成方法。利用H 2 O 2作为绿色氧化剂，利用2,2,2-三氟苯乙酮催化的烯丙基肟的氧化反应，以引入廉价且环境友好的方法合成取代的异恶唑啉。芳香族和脂肪族部分的各种取代方式都具有良好的耐受性，从而导致异恶唑啉的产率中等至优异。
• Manganese-Promoted Oxidative Cyclization of Unsaturated Oximes Using Molecular Oxygen in Air under Ambient Conditions
  作者：Daisuke Yamamoto、Takuto Oguro、Yuuki Tashiro、Masayuki Soga、Kazuhito Miyashita、Yoshiaki Aso、Kazuishi Makino

  DOI：10.1002/ejoc.201600998

  日期：2016.11

  A highly efficient manganese-promoted oxidative cyclization of unsaturated oximes to afford the corresponding 4,5-dihydroisoxazoline alcohols was developed. A very low loading (generally 0.1–0.2 mol-%) of Mn(acac)3 (acac = acetylacetonate) promoted the oxidative cyclization through the direct incorporation of molecular oxygen present in air (open flask) at room temperature.

  开发了一种高效的锰促进的不饱和肟氧化环化，以提供相应的 4,5-二氢异恶唑啉醇。Mn(acac)3（acac = 乙酰丙酮化物）的负载非常低（通常为 0.1–0.2 mol-%）通过在室温下直接掺入空气（开口烧瓶）中存在的分子氧来促进氧化环化。
• Organophotocatalytic Generation of N- and O-Centred Radicals Enables Aerobic Oxyamination and Dioxygenation of Alkenes
  作者：Xiao-Qiang Hu、Jun Chen、Jia-Rong Chen、Dong-Mei Yan、Wen-Jing Xiao

  DOI：10.1002/chem.201602597

  日期：2016.9.26

  applied for the first time to the direct conversion of N−H and O−H bonds into N‐ and O‐centred radicals, enabling a general and selective oxidative radical oxyamination and dioxygenation of various β,γ‐unsaturated hydrazones and oximes. In the reaction, O2 was employed not only as a terminal oxidant but also as the oxygen source. This protocol provided efficient access to the synthesis of various synthetically

  TEMPO和光氧化还原的催化合作策略首次应用于将N-H和O-H键直接转化为N-和O-中心的自由基，从而实现各种β，γ的一般和选择性氧化自由基的氧化和双加氧作用不饱和的和肟。在该反应中，不仅将O 2用作末端氧化剂，而且还将其用作氧源。该方案为在无金属和温和的反应条件下有效地合成各种重要的合成和生物学重要的吡唑啉，哒嗪和异恶唑啉衍生物提供了有效的途径。机理研究表明，协同有机光催化系统通过两个单电子转移（SET）过程起作用。