1-(2-iodobenzyl)piperidine | 76464-88-5

• 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-(2-iodobenzyl)piperidine
• 英文别名: 1-[(2-iodophenyl)methyl]piperidine
• CAS: 76464-88-5
• 化学式: C₁₂H₁₆IN
• mdl: MFCD06797849
• 分子量: 301.17
• InChiKey: OBPRBFCDPRYNIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  苯基溴化镁 、 1-(2-iodobenzyl)piperidine 在 iron(III)-acetylacetonate 作用下， 以 乙醚 、 甲基叔丁基醚 为溶剂， 以82%的产率得到1-苄基-2-苯基哌啶
  参考文献：
  名称：

  Yoshikai, Naohiko; Mieczkowski, Adam; Matsumoto, Arimasa, Journal of the American Chemical Society, 2010, vol. 132, p. 5568 - 5569

  摘要：

  DOI：
• 作为产物：
  描述：

  哌啶 、 邻碘氯苄 以 甲苯 为溶剂， 以98%的产率得到1-(2-iodobenzyl)piperidine
  参考文献：
  名称：

  胺通过1,5-氢转移的α-烷基化

  摘要：

  衍生自N-（2-碘苄基）'保护的'胺的自由基进行1,5-氢转移，得到更稳定的α-氨基，这些自由基随后可被缺乏电子的烯烃捕获。

  DOI：

  10.1039/c39940000883

文献信息

• Kinetics of the Oxidative Addition ofortho-Substituted Aryl Halides to Palladium(0) Complexes
  作者：Mouad Alami、Christian Amatore、Samia Bensalem、Abdelharim Choukchou-Brahim、Anny Jutand

  DOI：10.1002/1099-0682(200109)2001:10<2675::aid-ejic2675>3.0.co;2-j

  日期：2001.9

  participate in the oxidative addition by a preliminary complexation of the active Pd0(PPh3)2 or Pd0(dppp) complex. The observed decelerating effect induced by the ortho substituents is due to steric hindrance and electronic donor effects and is less important for aryl bromides than for aryl iodides; ortho-substituted aryl iodides remain more reactive than ortho-substituted aryl bromides for both ligands

  邻位取代芳基卤化物氧化加成的速率常数，o-Z -C6H4-X [X = I, Br; Z = OMe, NEt2, N(CH2)5] 到 Pd0(PPh3)4 或 Pd0(dba)(dppp) 从 Pd0(dba)2 和 1 equiv 生成。dppp 的确定。邻位取代的芳基卤化物的氧化加成比相应的未取代或间位取代的芳基卤化物的氧化加成慢。此处研究的邻位取代基不通过活性 Pd0(PPh3)2 或 Pd0(dppp) 复合物的初步络合参与氧化加成。观察到的由邻位取代基引起的减速效应是由于空间位阻和电子供体效应，对于芳基溴化物不如芳基碘化物重要；对于配体 PPh3 和 dppp，邻位取代芳基碘化物比邻位取代芳基溴化物更具反应性。
• New Functional Derivatives of 9-Phenylquinine
  作者：Jacek Skarżewski、Przemysaw Boratyński

  DOI：10.1055/s-0029-1216933

  日期：2009.9

  A rapid synthesis of various 9-aryl derivatives of quinine is presented. They are obtained via coupling reactions of functionalized arylmagnesium halides and 9-chloroquinine.

  本文介绍了奎宁的各种 9-芳基衍生物的快速合成方法。它们是通过官能化芳基卤化镁和 9-氯奎宁的偶联反应获得的。
• A Sn atom-economical approach toward arylstannanes: Ni-catalysed stannylation of aryl halides using Bu₃SnOMe
  作者：Kimihiro Komeyama、Ryota Asakura、Ken Takaki

  DOI：10.1039/c5ob01096a

  日期：——

  straightforward approaches for the preparation of organostannane compounds. Although a wide variety of methods are now available, all protocols require the use of highly nucleophilic organometals or wasteful stannyl sources like distannanes. Here, we report a new nickel-catalysed stannylation of aryl and alkenyl-halides using Bu3SnOMe as a stannyl source to afford aryl and vinyl-stannanes, respectively. This

  碳-卤素键的锡烷基化是制备有机锡烷化合物的最有前途和最直接的方法之一。尽管现在有各种各样的方法可用，但是所有方案都要求使用高度亲核的有机金属或像二锡烷之类的浪费的苯乙烯原料。在这里，我们报告了一种新的镍催化的芳基和卤代烷基苯磺酸盐，使用Bu 3 SnOMe作为苯乙烯源，分别提供了芳基和乙烯基-锡烷。该方法不仅能使溴化物，而且能使氯化物和三氟甲磺酸酯进行甲锡烷基化，从而提供官能化的芳基-和链烯基-stantanes，而不会释放出浪费且有毒的苯乙烯基副产物。
• Radioiodine containing amines, their preparation and their use as brain imaging agents
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0011858A1

  公开（公告）日：1980-06-11

  Certain radioiodine containing amines useful as brain imaging agents as well as their preparation are disclosed. The compounds of the invention are represented by the formula Wherein I is a radioisotope of iodine with 1-123 being preferred, R is lower alkyl or halogen, R and R2 are the same or different and are selected from the group consisting of hydrogen and lower alkyl, R3 and R4 are the same or different and are selected from the group consisting of hydrogen, alkyl, aryl, substituted aryl, aralkyl, substituted aralkyl and substituted carbamoylmethyl or R3 and R4 taken together with the nitrogen to which they are attached form a 5- or 6-membered ring which may be substituted with one or more lower alkyl groups, x is 0 to 4, y is 0 to 3 and z is 0 or 1, and pharmaceutically acceptable acid addition salts thereof.

  本发明公开了某些可用作脑成像剂的含放射性碘胺及其制备方法。本发明的化合物由式表示 其中，I 是碘的放射性同位素，优选 1-123；R 是低级烷基或卤素；R 和 R2 相同或不同，且选自由氢和低级烷基组成的组；R3 和 R4 相同或不同，且选自由氢、烷基、芳基、取代芳基、芳烷基、取代芳烷基和取代氨基甲酰基组成的组、或 R3 和 R4 与它们所连接的氮一起形成可被一个或多个低级烷基取代的 5 或 6 元环，x 为 0 至 4，y 为 0 至 3，z 为 0 或 1，以及它们的药学上可接受的酸加成盐。
• High-yielding synthesis of 1-isoindolinone derivatives via palladium-catalysed cycloaminocarbonylation
  作者：Diána Marosvölgyi-Haskó、Attila Takács、Zsuzsanna Riedl、László Kollár

  DOI：10.1016/j.tet.2010.11.099

  日期：2011.2

  1-Isoindolinone derivatives were synthesised in high yields (up to 89%) by using 2-iodobenzyl bromide and 2-iodobenzylamine as bifunctional substrates in palladium-catalysed carbonylation. Depending on the N-nucleophiles, two types of compounds were synthesised with 2-iodobenzyl bromide: the use of primary amines, including amino acid methylesters, resulted in the formation of N-substituted 1-isoindolinones, while secondary amines react both with the benzyl bromide and iodoarene moieties resulting in the corresponding ortho-(N-piperidino/morpholinomethyl)-benzamides. The parent 1-isoindolinone was obtained in a facile, highly chemoselective intramolecular aminocarbonylation of 2-iodobenzylamine. The mechanistic details of the ring-closure reaction and the conditions leading to side-products are discussed as well. (C) 2010 Elsevier Ltd. All rights reserved.