N-anthracenoyl-3,3-dimethyl-5-hydroxy-1,2-isoxazolidine | 1416969-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-anthracenoyl-3,3-dimethyl-5-hydroxy-1,2-isoxazolidine
• 英文别名: Anthracen-9-yl-(5-hydroxy-3,3-dimethyl-1,2-oxazolidin-2-yl)methanone；anthracen-9-yl-(5-hydroxy-3,3-dimethyl-1,2-oxazolidin-2-yl)methanone
• CAS: 1416969-40-8
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: XZQKDNAWBBWVFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-anthracenoyl-3,3-dimethyl-5-hydroxy-1,2-isoxazolidine 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-[2-(Anthracene-9-carbonyl)-3,3-dimethyl-1,2-oxazolidin-5-yl]-5-bromopyrimidine-2,4-dione
  参考文献：
  名称：

  N,O-Nucleosides from Ene Reactions of Nitrosocarbonyl Intermediates with the 3-Methyl-2-buten-1-ol

  摘要：

  Nitrosocarbonyl intermediates undergo ene reactions with allylic alcohols, affording regioisomeric adducts in fair yields. Nitrosocarbonyl benzene reacts with 3-methyl-2-buten-1-ol and follows a Markovnikov orientation and abstracts preferentially the twix hydrogens over the lone ones. With the more sterically demanding nitrosocarbonyl mesitylene and anthracene, the Markovnikov directing effect is relieved and lone abstraction is observed, affording the 5-hydroxy-isoxazolidines that serve as synthons for the preparation of N,O-nucleoside analogues according to the Vorbruggen protocol.

  DOI：

  10.1021/jo302346a
• 作为产物：
  描述：

  蒽-9-甲醛肟 在 吡啶 、 N-氯代丁二酰亚胺 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 48.0h， 生成 N-anthracenoyl-3,3-dimethyl-5-hydroxy-1,2-isoxazolidine
  参考文献：
  名称：

  N,O-Nucleosides from Ene Reactions of Nitrosocarbonyl Intermediates with the 3-Methyl-2-buten-1-ol

  摘要：

  Nitrosocarbonyl intermediates undergo ene reactions with allylic alcohols, affording regioisomeric adducts in fair yields. Nitrosocarbonyl benzene reacts with 3-methyl-2-buten-1-ol and follows a Markovnikov orientation and abstracts preferentially the twix hydrogens over the lone ones. With the more sterically demanding nitrosocarbonyl mesitylene and anthracene, the Markovnikov directing effect is relieved and lone abstraction is observed, affording the 5-hydroxy-isoxazolidines that serve as synthons for the preparation of N,O-nucleoside analogues according to the Vorbruggen protocol.

  DOI：

  10.1021/jo302346a

文献信息

• From the Ene Reaction of Nitrosocarbonyl Intermediates with 3-Methylbut-2-en-1-ol, a New Class of Purine N,O-Nucleoside Analogues
  作者：Paolo Quadrelli、Mariella Mella、Serena Carosso、Bruna Bovio

  DOI：10.1055/s-0032-1316916

  日期：——

  choice for the preparation of N,O-nucleoside analogues containing purine rings by means of the Vorbrüggen protocol. Sterically encumbered nitrosocarbonyl derivatives of mesitylene or anthracene undergo ene reactions with 3-methylbut-2-en-1-ol to give the corresponding the 5-hydroxyisoxazolidine adducts in fair yields. According to the proposed mechanism, these heterocycles are derived from the anti-Markovnikov

  摘要 立体上受到干扰的1，3，5-三甲基苯或蒽的亚硝基羰基衍生物与3-甲基丁-2-烯-1-醇进行烯反应，以适当的收率得到相应的5-羟基异恶唑烷加合物。根据所提出的机理，这些杂环是从烯反应的反马尔科夫尼科夫方向衍生的。乙酸异恶唑烷-5-基酯衍生物是通过Vorbrüggen方案制备含嘌呤环的N，O-核苷类似物的首选合成子。 立体上受到干扰的1，3，5-三甲基苯或蒽的亚硝基羰基衍生物与3-甲基丁-2-烯-1-醇进行烯反应，以适当的收率得到相应的5-羟基异恶唑烷加合物。根据所提出的机理，这些杂环是从烯反应的反马尔科夫尼科夫方向衍生的。乙酸异恶唑烷-5-基酯衍生物是通过Vorbrüggen方案制备含嘌呤环的N，O-核苷类似物的首选合成子。
• <i>N</i>,<i>O</i>-Nucleosides from Ene Reactions of Nitrosocarbonyl Intermediates with the 3-Methyl-2-buten-1-ol
  作者：Paolo Quadrelli、Mariella Mella、Serena Carosso、Bruna Bovio

  DOI：10.1021/jo302346a

  日期：2013.1.18

  Nitrosocarbonyl intermediates undergo ene reactions with allylic alcohols, affording regioisomeric adducts in fair yields. Nitrosocarbonyl benzene reacts with 3-methyl-2-buten-1-ol and follows a Markovnikov orientation and abstracts preferentially the twix hydrogens over the lone ones. With the more sterically demanding nitrosocarbonyl mesitylene and anthracene, the Markovnikov directing effect is relieved and lone abstraction is observed, affording the 5-hydroxy-isoxazolidines that serve as synthons for the preparation of N,O-nucleoside analogues according to the Vorbruggen protocol.