tert-butyl 4-(hydroxy(phenyl)methyl)azete-1(2H)-carboxylate | 1537176-19-4

• 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: tert-butyl 4-(hydroxy(phenyl)methyl)azete-1(2H)-carboxylate
• 英文别名: tert-butyl 4-[hydroxy(phenyl)methyl]-2H-azete-1-carboxylate
• CAS: 1537176-19-4
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: CNXDIPXKQOQKGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-Boc-3-羟基氮杂环丁烷 在 四甲基乙二胺 、 仲丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 环己烷 、 mineral oil 为溶剂， 反应 4.0h， 生成 tert-butyl 4-(hydroxy(phenyl)methyl)azete-1(2H)-carboxylate
  参考文献：
  名称：

  Generation and Electrophile Trapping of N-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines

  摘要：

  s-BuLi-induced alpha-lithiation-elimination of LiOMe from N-Boc-3-methoxyazetidine and further in situ alpha-lithiation generates N-Boc-2-lithio-2-azetine which can be trapped with electrophiles, either directly (carbonyl or heteroatom electrophiles) or after transmetalation to copper (allowing allylations and propargylations), providing a concise access to 2-substituted 2-azetines.

  DOI：

  10.1021/ol403626k

文献信息

• Development of a Continuous Flow Synthesis of 2-Substituted Azetines and 3-Substituted Azetidines by Using a Common Synthetic Precursor
  作者：Marco Colella、Pantaleo Musci、Debora Cannillo、Mauro Spennacchio、Andrea Aramini、Leonardo Degennaro、Renzo Luisi

  DOI：10.1021/acs.joc.1c01297

  日期：2021.10.15

  The generation and functionalization, under continuous flow conditions, of two different lithiated four-membered aza-heterocycles is reported. N-Boc-3-iodoazetidine acts as a common synthetic platform for the genesis of C3-lithiated azetidine and C2-lithiated azetine depending on the lithiation agent. Flow technology enables easy handling of such lithiated intermediates at much higher temperatures

  报道了在连续流动条件下两种不同锂化四元氮杂杂环的生成和功能化。N -Boc-3-iodoazetidine 作为通用合成平台，用于根据锂化剂生成 C3-锂化氮杂环丁烷和 C2-锂化氮杂环丁烷。与批处理相比，流动技术可以在更高的温度下轻松处理此类锂化中间体。流动技术与环戊基甲基醚作为对环境负责的溶剂相结合，使我们能够解决可持续性问题。
• Generation and Electrophile Trapping of <i>N</i>-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines
  作者：David M. Hodgson、Christopher I. Pearson、Madiha Kazmi

  DOI：10.1021/ol403626k

  日期：2014.2.7

  s-BuLi-induced alpha-lithiation-elimination of LiOMe from N-Boc-3-methoxyazetidine and further in situ alpha-lithiation generates N-Boc-2-lithio-2-azetine which can be trapped with electrophiles, either directly (carbonyl or heteroatom electrophiles) or after transmetalation to copper (allowing allylations and propargylations), providing a concise access to 2-substituted 2-azetines.