N,N-dibenzyl-1-(3,3-dimethyloxiran-2-yl)methanamine | 1306772-35-9

• 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: N,N-dibenzyl-1-(3,3-dimethyloxiran-2-yl)methanamine
• 英文别名: 1-(N,N-dibenzylamino)-2,3-epoxy-3-methylbutane
• CAS: 1306772-35-9
• 化学式: C₁₉H₂₃NO
• 分子量: 281.398
• InChiKey: HDFURAVXBPQNSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  15.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-dibenzyl-1-(3,3-dimethyloxiran-2-yl)methanamine 在 四氟硼酸-二乙醚络合物 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以88%的产率得到1-(N,N-dibenzylamino)-3-fluoro-3-methylbutan-2-ol
  参考文献：
  名称：

  Ring-Opening Hydrofluorination of 2,3- and 3,4-Epoxy Amines by HBF₄·OEt₂: Application to the Asymmetric Synthesis of (S,S)-3-Deoxy-3-fluorosafingol

  摘要：

  Treatment of a range of 2,3- and 3,4-epoxy amines with HBF4 center dot OEt2 at room temperature results in fast and efficient S(N)2-type ring-opening hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method, The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.

  DOI：

  10.1021/jo200517w
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 在 双氧水 、 三乙酰氧基硼氢化钠 、 potassium hydrogencarbonate 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 18.5h， 生成 N,N-dibenzyl-1-(3,3-dimethyloxiran-2-yl)methanamine
  参考文献：
  名称：

  Ring-Opening Hydrofluorination of 2,3- and 3,4-Epoxy Amines by HBF₄·OEt₂: Application to the Asymmetric Synthesis of (S,S)-3-Deoxy-3-fluorosafingol

  摘要：

  Treatment of a range of 2,3- and 3,4-epoxy amines with HBF4 center dot OEt2 at room temperature results in fast and efficient S(N)2-type ring-opening hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method, The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.

  DOI：

  10.1021/jo200517w

文献信息

• Oxidation Under Reductive Conditions: From Benzylic Ethers to Acetals with Perfect Atom‐Economy by Titanocene(III) Catalysis
  作者：Pierre Funk、Ruben B. Richrath、Fabian Bohle、Stefan Grimme、Andreas Gansäuer

  DOI：10.1002/anie.202013561

  日期：2021.3

  oxygen rebound as a reductive elimination. The reaction mechanism was studied by high‐level dispersion corrected hybrid functional DFT with implicit solvation. The low‐energy conformational space was searched by the efficient CREST program. The stereoselectivity was deduced from the lowest lying benzylic radical structures and their conformations are controlled by hyperconjugative interactions and steric

  此处描述的是钛茂金属催化的反应，分别由苄基醚和苄基胺与侧链环氧化合物合成乙缩醛和半缩醛。反应通过单电子步骤催化进行。氧化加成包括环氧化物开口。H原子转移可生成苄基自由基，是自由基易位的步骤，而有机金属氧的反弹则是还原性的消除。通过高水平色散校正的含隐溶剂化混合功能DFT研究了反应机理。通过高效的CREST程序搜索低能构象空间。立体选择性由最低的苄基自由基结构推导而来，其构象由钛茂催化剂与底物的芳基之间的超共轭相互作用和空间相互作用控制。一个有趣的机理方面是苄基中心的氧化在还原条件下发生。
• Ring-Opening Hydrofluorination of 2,3- and 3,4-Epoxy Amines by HBF₄·OEt₂: Application to the Asymmetric Synthesis of (<i>S</i>,<i>S</i>)-3-Deoxy-3-fluorosafingol
  作者：Alexander J. Cresswell、Stephen G. Davies、James A. Lee、Melloney J. Morris、Paul M. Roberts、James E. Thomson

  DOI：10.1021/jo200517w

  日期：2011.6.3

  Treatment of a range of 2,3- and 3,4-epoxy amines with HBF4 center dot OEt2 at room temperature results in fast and efficient S(N)2-type ring-opening hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method, The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.