N-allyl [4-phenoxy]aniline | 823221-75-6

• 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-allyl [4-phenoxy]aniline
• 英文别名: 4-Phenoxy-N-(prop-2-en-1-yl)aniline；4-phenoxy-N-prop-2-enylaniline
• CAS: 823221-75-6
• 化学式: C₁₅H₁₅NO
• mdl: MFCD16470069
• 分子量: 225.29
• InChiKey: GDSXOSQJTMVKTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-allyl [4-phenoxy]aniline 在 四氧化锇 、 ammonium cerium(IV) nitrate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 2.0h， 生成 3-[methyl-(4-phenoxy-phenyl)-amino]-propane-1,2-diol
  参考文献：
  名称：

  Cerium ammonium nitrate: a new catalyst for regioselective protection of glycols

  摘要：

  The regioselective introduction of a methoxymethyl (MOM) group on different type of glycols via an orthoester intermediate was investigated. The novelty presented in this study is the use of ceric ammonium nitrate instead of the previously employed camphorsulfonic acid as catalyst. The monoprotection reaction was revealed to be highly selective when the glycol moiety was in the presence of an ether functionality. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.097
• 作为产物：
  描述：

  3-氯丙烯 、 4-氨基二苯醚 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 以81%的产率得到N-allyl [4-phenoxy]aniline
  参考文献：
  名称：

  Cerium ammonium nitrate: a new catalyst for regioselective protection of glycols

  摘要：

  The regioselective introduction of a methoxymethyl (MOM) group on different type of glycols via an orthoester intermediate was investigated. The novelty presented in this study is the use of ceric ammonium nitrate instead of the previously employed camphorsulfonic acid as catalyst. The monoprotection reaction was revealed to be highly selective when the glycol moiety was in the presence of an ether functionality. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.097

文献信息

• Synthesis of quaternary α-benzyl- and α-allyl-α-methylamino cyclobutanones
  作者：Lorenza Ghisu、Nicola Melis、Francesco Secci、Pierluigi Caboni、Angelo Frongia

  DOI：10.1016/j.tet.2016.10.024

  日期：2016.12

  important quaternary α-benzyl- and α-allyl-α-methylamino cyclobutanones in good to high yield, via a sequential one-pot methylation/sigmatropic rearrangement, has been accomplished for the first time. The quaternary α-alkyl-α-amino cyclobutanones could be further manipulated, affording synthetically interesting scaffolds such as highly substituted tryptamines and cyclobuta-fused indolines.

  首次完成了通过连续的一锅甲基化/σ重排，以良好至高收率构建合成重要的季铵化α-苄基-和α-烯丙基-α-甲基氨基环丁酮的简单实用方案。季α-烷基-α-氨基环丁酮可以被进一步处理，从而提供合成上令人感兴趣的支架，例如高度取代的色胺和与环丁烯融合的二氢吲哚。
• Photo‐triggered Intramolecular Radical Tandem Regioselective Alkylation/Cyclization of 1, <scp>6‐Dienes</scp> with <scp>Redox‐Active</scp> Esters Enabled by an <scp>EDA</scp> Complex
  作者：Bin Sun、Lan Ling、Xiaohui Zhuang、Lulu Yang、Jieli Yin、Can Jin

  DOI：10.1002/cjoc.202200516

  日期：2023.1

  radical tandem alkylation/cyclization between 1,6-dienes and redox-active esters has been developed, affording a series of N-aryl pyrrolidine-2-ones in moderate to good yields. The transformation is driven by the formation of an electron-donor-acceptor (EDA) complex and a subsequent single electron transfer (SET) process. This photocatalyst-free protocol features excellent regioselectivity, mild conditions

  已经开发了 1,​​6-二烯和氧化还原活性酯之间的光催化剂和金属自由基串联烷基化/环化，以中等到良好的收率提供了一系列N-芳基吡咯烷-2-酮。这种转变是由电子供体受体 (EDA) 复合物的形成和随后的单电子转移 (SET) 过程驱动的。这种无光催化剂的方案具有出色的区域选择性、温和的条件和广泛的底物范围，可轻松获得 3-alkyl-3,4-dimethyl-1-phenylpyrrolidin-2-one。
• 10.1002/anie.202407841
  作者：Liu, Shupeng、Xu, Tianyi、Liu, Yuting、Wang, Youliang

  DOI：10.1002/anie.202407841

  日期：——

  meta-Thermocycloadditions of benzene rings was realized for the first time. Distinct to the meta-photocycloadditions, this reaction was proposed to proceed via [4π+2π] cycloadditions of Wheland intermediates from the electrophilic dearomatization of benzene rings. A broad spectrum of readily available C(sp2)-rich aniline-tethered enynes were transformed into C(sp3)-rich 3D complex polycyclic architectures

  首次实现了苯环间位热环加成反应。与间位光环加成不同，该反应被认为是通过苯环亲电脱芳构化过程中 Wheland 中间体的 [4π+2π] 环加成进行的。只需在 TFA 中搅拌，即可将多种容易获得的富含 C(sp 2 ) 的苯胺束缚烯炔转化为富含 C(sp 3 ) 的 3D 复杂多环结构。
• Cerium ammonium nitrate: a new catalyst for regioselective protection of glycols
  作者：María J. Comin、Eleonora Elhalem、Juan B. Rodriguez

  DOI：10.1016/j.tet.2004.09.097

  日期：2004.12

  The regioselective introduction of a methoxymethyl (MOM) group on different type of glycols via an orthoester intermediate was investigated. The novelty presented in this study is the use of ceric ammonium nitrate instead of the previously employed camphorsulfonic acid as catalyst. The monoprotection reaction was revealed to be highly selective when the glycol moiety was in the presence of an ether functionality. (C) 2004 Elsevier Ltd. All rights reserved.