2-iodomethyl-1-(p-toluenesulfonyl)piperidine | 63587-40-6

• 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: 2-iodomethyl-1-(p-toluenesulfonyl)piperidine
• 英文别名: 2-(iodomethyl)-1-tosylpiperidine；Piperidine, 2-(iodomethyl)-1-[(4-methylphenyl)sulfonyl]-；2-(iodomethyl)-1-(4-methylphenyl)sulfonylpiperidine
• CAS: 63587-40-6
• 化学式: C₁₃H₁₈INO₂S
• 分子量: 379.262
• InChiKey: DTPPAKKZZYRTCL-UHFFFAOYSA-N

物化性质

• 沸点：
  451.1±47.0 °C(Predicted)
• 密度：
  1.574±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-hexenyl methanesulfonate 在 aluminum oxide 、 氢氧化钾 、 Oxone 、 potassium iodide 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 2-iodomethyl-1-(p-toluenesulfonyl)piperidine
  参考文献：
  名称：

  N-甲苯磺酰基吡咯烷和哌啶的一种新的、简单的合成方法

  摘要：

  通过 Oxone® 氧化 KI 促进的不饱和甲苯磺酰胺的碘环化以良好的收率提供了 N-甲苯磺酰基碘吡咯烷和哌啶。介绍了一种将醇转化为甲苯磺酰胺的简单新方法。

  DOI：

  10.1055/s-2006-942488

文献信息

• Palladium-catalyzed intramolecular aminoiodination of alkenes using molecular oxygen as oxidant
  作者：Lu Chen、Xianglin Luo、Yibiao Li

  DOI：10.1007/s00706-016-1819-2

  日期：2017.5

  AbstractMolecular oxygen as oxidant to promote palladium-catalyzed intramolecular aminoiodination of alkenes has been described. The yields are excellent and show high exo-selectivities with various substrates. Graphical abstract

  摘要已经描述了分子氧作为氧化剂以促进钯催化的烯烃的分子内氨基碘化。产率是极好的，并显示出高的外型与各种基材-selectivities。 图形概要
• Practical Synthesis of Halogenated <i>N</i> ‐Heterocycles via Electrochemical Anodic Oxidation of Unactivated Alkenes
  作者：Yanyang He、Xiaowen Qin、Xinxu He、Xiao‐Feng Wu、Zhiping Yin

  DOI：10.1002/ejoc.202101189

  日期：2021.11.15

  A general and efficient intramolecular halo-amination of unactivated alkenes for the synthesis of various halogenated N-heterocycles was developed via electrochemical anodic oxidation. This protocol proceeds in a simple undivided cell by employing LiI or LiBr as redox mediums and halogen sources. A wide range of halogenated N-heterocycles, including three-, five-, and six-membered N-heterocycles were

  通过电化学阳极氧化开发了用于合成各种卤化N-杂环的未活化烯烃的通用且有效的分子内卤化胺化。该协议通过使用 LiI 或 LiBr 作为氧化还原介质和卤素源，在一个简单的未分隔单元中进行。在室温下以中等至良好的产率构建了范围广泛的卤化N-杂环，包括三元、五元和六元N-杂环。值得注意的是，这种电化学氧化转化避免了使用外部氧化剂和强碱，因此代表了一种环境友好的方法。
• Practical and Convenient Synthesis of <i>N</i>-Heterocycles:  Stereoselective Cyclization of <i>N</i>-Alkenylamides with <i>t</i>-BuOI under Neutral Conditions
  作者：Satoshi Minakata、Yoshinobu Morino、Yoji Oderaotoshi、Mitsuo Komatsu

  DOI：10.1021/ol061182q

  日期：2006.7.1

  [Structure: see text] tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for the cyclization of N-alkenylamides leading to a variety of N-heterocycles under extremely mild conditions. When N-alkenylsulfonamides were employed in the reaction, three- to six-membered saturated N-heterocycles were obtained in good to excellent yields with complete stereoselectivity. The method was applicable

  [结构：见正文]叔丁基次碘酸盐（t-BuOI）被发现是在极端温和条件下环化N-烯基酰胺的强大试剂，可导致多种N-杂环。当在反应中使用N-烯基磺酰胺时，以完全的立体选择性，以良好至优异的产率获得了三元至六元饱和N-杂环。该方法适用于烯基苯甲酰胺衍生物的环化以提供N-，O-或N-，S-杂环。
• MnI2-catalyzed regioselective intramolecular iodoamination of unfunctionalized olefins
  作者：Hui Sun、Bin Cui、Gong-Qing Liu、Yue-Ming Li

  DOI：10.1016/j.tet.2016.09.038

  日期：2016.11

  MnI2-catalyzed intramolecular iodoamination of unfunctionalized olefins was reported. Interaction of MnI2 with N-alkenyl amine/sulfonamide gave NRMnI which produced a CH2MnI intermediate via intramolecular aminometallation of CC double bond. Reductive elimination of CH2I from CH2MnI produced iodomethyl heterocycle with the release of Mn(0) which was confirmed by XPS and XRD experiments.

  报导了MnI 2催化的未官能化烯烃的分子内碘化。MnI 2与N-链烯基胺/磺酰胺的相互作用产生了NRMnI，它通过C C双键的分子内氨基金属化反应生成了CH 2 MnI中间体。从XPS和XRD实验中证实，从CH 2 MnI中还原消除CH 2 I产生了碘甲基杂环，并释放了Mn（0）。
• Electrophilic cyclization of N-alkenylamides using a chloramine-T/I2 system
  作者：Yoshinobu Morino、Ikumasa Hidaka、Yoji Oderaotoshi、Mitsuo Komatsu、Satoshi Minakata

  DOI：10.1016/j.tet.2006.10.003

  日期：2006.12

  A new protocol for the cyclization of N-alkenylamides using chloramine-T and iodine is described. When N-alkenylsulfonamides are treated with chloramine-T and iodine, three- to six-membered N-heterocycles are obtained with complete stereoselectivity. The method is compatible with the cyclization of the allylbenzamide or allylbenzthioamide to afford an oxazoline or thiazoline derivative, respectively. Mechanistic studies indicate that the chloramine-T/I-2 system functions as an effective iodonium species. (c) 2006 Elsevier Ltd. All rights reserved.