1-(phenylmethyl)-4-(2-cyanophenyl)-1-piperidine | 115661-39-7

• 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-(phenylmethyl)-4-(2-cyanophenyl)-1-piperidine
• 英文别名: 2-(1-benzyl-4-piperidinyl)aminobenzonitrile；2-[[1-(Phenylmethyl)-4-piperidinyl]amino]benzonitrile；2-[(1-benzylpiperidin-4-yl)amino]benzonitrile
• CAS: 115661-39-7
• 化学式: C₁₉H₂₁N₃
• mdl: MFCD13808493
• 分子量: 291.396
• InChiKey: PIHPKHRKNRENNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.315
• 拓扑面积：
  39.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-苄基哌啶酮 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 81.67h， 生成 1-(phenylmethyl)-4-(2-cyanophenyl)-1-piperidine
  参考文献：
  名称：

  Conformational Switching and the Synthesis of Spiro[2H-indol]-3(1H)-ones by Radical Cyclization

  摘要：

  Radical cyclization of 1-(2-bromophenylamino)cyclohexanecarbonitriles (3, X = CH) and 4-(2-bromophenylamino)-4-piperidinecarbonitriles (3, X = N) provide spiro[2H-indole-2-cyclohexan]3(1H)-imines (5, X = CH) and spiro[2H-indole-2,4'-piperidin]-3(1H)-imines (5, X = N), respectively, in 33-57% yields. This contradicts a recent report that 1-(2-bromophenylamino)cyclohexane-carbonitrile (3, X-R-2 = CH2), treated under apparently identical conditions, led only to nitrile transfer product 6 (X-R-2 = CH2). Acidic hydrolyses of the imines provide the corresponding ketones 2 in quantitative yields. Single-crystal X-ray analyses of ketone 2e and nitrile 3e indicate that the relative configuration of the aromatic nitrogen has been inverted during the cyclization. In addition, NOE NMR analyses of spiroindolepiperidine 2e and its aniline-nitrogen-methylated analogue 10a show that the relative conformation of the piperidine ring has inverted. Thus, methylation of 2c acts as a conformational "switch" for the spiroindolepiperidine ring system.

  DOI：

  10.1021/jo970105t

文献信息

• Process for ortho-cyanation of phenols or phenylamines
  申请人：Shionogi & Co., Ltd.

  公开号：US04774331A1

  公开（公告）日：1988-09-27

  A process for ortho-cyanation of phenols or phenylamines which comprises reacting a phenyl compound having hydroxy or optionally substituted amino or cyclic amino, of which ortho position is vacant, with trichloroacetonitrile, C.sub.1 -C.sub.5 alkyl thiocyanate or C.sub.6 -C.sub.12 aryl thiocyanate in the presence of a boron trihalide and treating the resultant product with an alkali is provided, and said process is useful in the synthesis of intermediates for medicinals or pesticides.

  提供了一种酚或苯胺的邻位氰化过程，该过程包括将具有羟基或可选地取代氨基或环状氨基的苯基化合物与三氯乙腈、C1-C5烷基硫氰酸盐或C6-C12芳基硫氰酸盐在硼三卤化物的存在下反应，并用碱处理所得产物，所述过程用于合成药物或杀虫剂的中间体。
• US4774331A
  申请人：——

  公开号：US4774331A

  公开（公告）日：1988-09-27
• Conformational Switching and the Synthesis of Spiro[2<i>H</i>-indol]-3(1<i>H</i>)-ones by Radical Cyclization
  作者：Richard Sulsky、Jack Z. Gougoutas、John DiMarco、Scott A. Biller

  DOI：10.1021/jo970105t

  日期：1999.7.1

  Radical cyclization of 1-(2-bromophenylamino)cyclohexanecarbonitriles (3, X = CH) and 4-(2-bromophenylamino)-4-piperidinecarbonitriles (3, X = N) provide spiro[2H-indole-2-cyclohexan]3(1H)-imines (5, X = CH) and spiro[2H-indole-2,4'-piperidin]-3(1H)-imines (5, X = N), respectively, in 33-57% yields. This contradicts a recent report that 1-(2-bromophenylamino)cyclohexane-carbonitrile (3, X-R-2 = CH2), treated under apparently identical conditions, led only to nitrile transfer product 6 (X-R-2 = CH2). Acidic hydrolyses of the imines provide the corresponding ketones 2 in quantitative yields. Single-crystal X-ray analyses of ketone 2e and nitrile 3e indicate that the relative configuration of the aromatic nitrogen has been inverted during the cyclization. In addition, NOE NMR analyses of spiroindolepiperidine 2e and its aniline-nitrogen-methylated analogue 10a show that the relative conformation of the piperidine ring has inverted. Thus, methylation of 2c acts as a conformational "switch" for the spiroindolepiperidine ring system.