(5-methyl-3-(naphthalen-2-yl)-4,5-dihydroisoxazol-5-yl)methanol | 1221447-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (5-methyl-3-(naphthalen-2-yl)-4,5-dihydroisoxazol-5-yl)methanol
• 英文别名: (5-methyl-3-naphthalen-2-yl-4H-1,2-oxazol-5-yl)methanol
• CAS: 1221447-43-3
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: HNZITJXMPSGHFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2-(nitromethyl)naphthalene 在 三氟甲磺酸 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 17.5h， 生成 (5-methyl-3-(naphthalen-2-yl)-4,5-dihydroisoxazol-5-yl)methanol
  参考文献：
  名称：

  Catalytic Asymmetric Cycloadditions of Silyl Nitronates Bearing α-Aryl Group

  摘要：

  1,3-Dipolar cycloadditions of 2-alkylacroleins or atropaldehyde with triisopropylsilyl nitronates bearing an alpha-ary] group produced 3-aryl-2-isoxazolines having a chiral quaternary center in up to 94% ee and up to 88% yield with the aid of Corey's oxazaborolidine catalyst. Specifically, the TIPS nitronate with an alpha-(p-methoxyphenyl) group gave mainly the 2-isoxazolines having an all-carbon quaternary center.

  DOI：

  10.1021/acs.orglett.7b00558

文献信息

• 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。
• Palladium-Catalyzed Oxime Assisted Intramolecular Dioxygenation of Alkenes with 1 atm of Air as the Sole Oxidant
  作者：Ming-Kui Zhu、Jun-Feng Zhao、Teck-Peng Loh

  DOI：10.1021/ja100716x

  日期：2010.5.12

  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.
• Catalytic Asymmetric Cycloadditions of Silyl Nitronates Bearing α-Aryl Group
  作者：Minghui Jiang、Lifei Feng、Juanjuan Feng、Peng Jiao

  DOI：10.1021/acs.orglett.7b00558

  日期：2017.5.5

  1,3-Dipolar cycloadditions of 2-alkylacroleins or atropaldehyde with triisopropylsilyl nitronates bearing an alpha-ary] group produced 3-aryl-2-isoxazolines having a chiral quaternary center in up to 94% ee and up to 88% yield with the aid of Corey's oxazaborolidine catalyst. Specifically, the TIPS nitronate with an alpha-(p-methoxyphenyl) group gave mainly the 2-isoxazolines having an all-carbon quaternary center.