1-chloro-4-phenylpiperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-chloro-4-phenylpiperidine
• 英文别名: N-chloro-4-phenylpiperidine；1-Chloro-4-phenylpiperidine
• 化学式: C₁₁H₁₄ClN
• 分子量: 195.692
• InChiKey: YIPICMDIVDXPEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2,3,4-四氢萘 、 1-chloro-4-phenylpiperidine 在 ferrous(II) sulfate heptahydrate 、 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以26%的产率得到4-phenyl-1-(5,6,7,8-tetrahydronaphthalen-2-yl) piperidine
  参考文献：
  名称：

  铁催化的 N-氯胺直接芳香胺化

  摘要：

  报道了在铁催化下用 N-氯胺产生的胺自由基直接分子内和分子间胺化芳香族 C-H 键的优化程序。可以很容易地制备一系列取代的四氢喹啉，而扩展到苯并吗啉的合成范围更受限制。开发了一种直接的单锅变体，允许直接氧化 N-H/C-H 偶联。

  DOI：

  10.1002/ejoc.201900614
• 作为产物：
  描述：

  4-苯基哌啶 在 N-氯代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 1-chloro-4-phenylpiperidine
  参考文献：
  名称：

  Insertion of Arynes into N-Halo Bonds: A Direct Approach to o-Haloaminoarenes

  摘要：

  A new approach to access o-haloaminoarenes has been achieved by insertion of arynes into a nitrogen-halide bond (N-X). This transition-metal-free transformation displays a broad substrate scope of arynes, good compatibility with functional groups, and high regioselectivity. Representative transformations of the o-haloaminoarenes are described to highlight their utility for rapid access to diversely functionalized a minoarene derivatives.

  DOI：

  10.1021/ol401518c

文献信息

• Insertion of Arynes into <i>N</i>-Halo Bonds: A Direct Approach to <i>o</i>-Haloaminoarenes
  作者：Charles E. Hendrick、Stacey L. McDonald、Qiu Wang

  DOI：10.1021/ol401518c

  日期：2013.7.5

  A new approach to access o-haloaminoarenes has been achieved by insertion of arynes into a nitrogen-halide bond (N-X). This transition-metal-free transformation displays a broad substrate scope of arynes, good compatibility with functional groups, and high regioselectivity. Representative transformations of the o-haloaminoarenes are described to highlight their utility for rapid access to diversely functionalized a minoarene derivatives.
• US4468511A
  申请人：——

  公开号：US4468511A

  公开（公告）日：1984-08-28
• US2023/174506
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of <i>ortho</i>-Haloaminoarenes by Aryne Insertion of Nitrogen–Halide Bonds
  作者：Charles E. Hendrick、Qiu Wang

  DOI：10.1021/jo502541t

  日期：2015.1.16

  A rapid and general access to ortho-haloaminoarenes has been developed by aryne insertion into N-chloramine, N-bromoamine, and N-iodoamine bonds via two complementary protocols harnessing fluoride-promoted 1,2-elimination of ortho-trimethylsilyl aryltriflates. Typically, electron-deficient N-chloramines effectively react with aryne intermediates generated at elevated temperature with CsF, while less stable N-haloamines are found more efficient under milder, TBAF-mediated aryne formation at room temperature. Both protocols demonstrate a good level of regioselectivity and functional group tolerance. Efforts to elucidate the mechanism of NX insertion are also discussed. The practical value of this transformation is highlighted by rapid synthesis of novel analogues of the antipsychotic cariprazine.
• Iron‐Catalysed Direct Aromatic Amination with <i>N</i> ‐Chloroamines
  作者：Gayle E. Douglas、Steven A. Raw、Stephen P. Marsden

  DOI：10.1002/ejoc.201900614

  日期：2019.9

  optimized procedure for the direct intra‐ and intermolecular amination of aromatic C‐H bonds with aminium radicals generated from N‐chloroamines under iron catalysis is reported. A range of substituted tetrahydroquinolines could be readily prepared, while extension to the synthesis of benzomorpholines was more limited in scope. A direct one‐pot variant was developed, allowing direct formal oxidative N‐H/C‐H

  报道了在铁催化下用 N-氯胺产生的胺自由基直接分子内和分子间胺化芳香族 C-H 键的优化程序。可以很容易地制备一系列取代的四氢喹啉，而扩展到苯并吗啉的合成范围更受限制。开发了一种直接的单锅变体，允许直接氧化 N-H/C-H 偶联。