tert-butyl 2-(4-methoxyphenyl)piperidine-1-carboxylate

• 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: tert-butyl 2-(4-methoxyphenyl)piperidine-1-carboxylate
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: ZYLQYAXPYWOTOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(4-methoxyphenyl)piperidine-1-carboxylate 在 Phenomenex Lux cellulose-2 column 作用下， 以 正己烷 、 异丙醇 为溶剂， 生成 (2R)-tert-butyl 2-(4-methoxyphenyl)piperidine-1-carboxylate 、 (2S)-tert-butyl 2-(4-methoxyphenyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and kinetic resolution of N-Boc-2-arylpiperidines

  摘要：

  开发了一种使用手性碱的高效动力学拆分2-芳基哌啶的方法。

  DOI：

  10.1039/c4cc04576a
• 作为产物：
  描述：

  5-溴戊腈 在 甲醇 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.92h， 生成 tert-butyl 2-(4-methoxyphenyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and kinetic resolution of N-Boc-2-arylpiperidines

  摘要：

  开发了一种使用手性碱的高效动力学拆分2-芳基哌啶的方法。

  DOI：

  10.1039/c4cc04576a

文献信息

• Synthesis of 2-Arylpiperidines by Palladium Couplings of Aryl Bromides with Organozinc Species Derived from Deprotonation of <i>N</i>-Boc-Piperidine
  作者：Iain Coldham、Daniele Leonori

  DOI：10.1021/ol801579r

  日期：2008.9.1

  The organolithium species derived from proton abstraction of N-Boc-piperidine with s-BuLi and TMEDA can be transmetalated to the organozinc reagent, and this organometallic species can be coupled directly with aryl bromides in a Negishi-type reaction using palladium catalysis with the ligand tri-tert-butylphosphine (t-Bu3P-HBF4). The chemistry was applied to a very short synthesis of the alkaloid anabasine

  可以将N-Boc-哌啶与s-BuLi和TMEDA的质子抽象衍生的有机锂物质进行金属转移到有机锌试剂中，并且该有机金属物质可以在Negishi型反应中与钯配体催化直接与芳基溴偶联。三叔丁基膦（t-Bu3P-HBF4）。该化学方法用于非常短的生物碱金刚烷胺的合成。
• [Co(TPP)]‐Catalyzed Formation of Substituted Piperidines
  作者：Marianne Lankelma、Astrid M. Olivares、Bas de Bruin

  DOI：10.1002/chem.201900587

  日期：2019.4.17

  the [Co(TPP)]‐catalyzed formation of useful six‐membered N‐heterocyclic piperidines directly from linear aldehydes is presented herein. The piperidines were obtained in overall high yields, with linear alkenes being formed as side products in small amounts. A DFT study was performed to gain a deeper mechanistic understanding of the cobalt(II)‐porphyrin‐catalyzed formation of pyrrolidines, piperidines

  通过钴（III）-卡宾自由基中间体进行的自由基环化是合成（杂环）环状结构的有力方法。以最近报道的Co II催化的五元N-杂环吡咯烷的合成为基础卟啉，本文介绍了直接由线性醛类[Co（TPP）]催化形成的有用的六元N-杂环哌啶。以总的高收率获得哌啶，并以少量副产物形式形成直链烯烃。进行了DFT研究，以更深入地了解钴（II）-卟啉催化的吡咯烷，哌啶和线性烯烃的形成。计算表明，烯烃不可能通过预期的1,2-氢原子转移至卡宾碳而形成。取而代之的是，该计算与涉及苄基自由基形成，随后进行自由基反弹的闭环形成哌啶的途径是一致的。竞争性1
• Heterocyclization involving benzylic C(sp³)–H functionalization enabled by visible light photoredox catalysis
  作者：Ganesh Pandey、Ramkrishna Laha、Pradip Kumar Mondal

  DOI：10.1039/c9cc04287c

  日期：——

  A general and efficient method for heterocyclization involving benzylic C(sp3)–H functionalization enabled by visible light photoredox catalysis to access a wide range of structurally diverse oxygen as well as nitrogen heterocycles up to a gram scale is reported. The potential application of this new methodology is demonstrated by the total synthesis of (−)-codonopsinine and (+)-centrolobine. Herein

  据报道，一种通用有效的杂环化方法涉及苄基C（sp 3）–H官能团，该官能团通过可见光光氧化还原催化作用可访问范围广泛的结构多样的氧和氮杂环，直至克级。（-）-codonopsinine和（+）-centrolobine的总合成证明了这种新方法的潜在应用。在本文中提出了与氟化试剂不同，selectfluor用作氧化猝灭剂和氢自由基受体。
• Nickel‐Catalyzed Thermal Redox Functionalization of C(sp ³ )−H Bonds with Carbon Electrophiles**
  作者：Yuxin Gong、Lei Su、Zhaodong Zhu、Yang Ye、Hegui Gong

  DOI：10.1002/anie.202201662

  日期：2022.5.23

  Under thermal conditions, nickel-catalyzed C(sp3)−H redox functionalization with carbon electrophiles has been advanced to forge value-added C(sp3)−C bonds in good to excellent efficiency. This method emphasizes the use of external Zn as reductant and di-tert-butyl peroxide as an oxidant and shows remarkable compatibility with Ni-catalysis.

  在热条件下，镍催化的碳亲电试剂的 C(sp 3 )-H 氧化还原功能化已被推进，以形成具有良好至优异效率的增值 C(sp 3 )-C 键。该方法强调使用外部 Zn 作为还原剂和二叔丁基过氧化物作为氧化剂，并显示出与 Ni 催化的显着相容性。
• Copper Cyanide-Catalyzed Palladium Coupling of <i>N</i>-<i>tert</i>-Butoxycarbonyl-Protected α-Lithio Amines with Aryl Iodides or Vinyl Iodides
  作者：R. Karl Dieter、ShengJian Li

  DOI：10.1021/jo970985b

  日期：1997.10.1

  Treatment of (alpha-aminoalkyl)lithium reagents with aryl iodides in the presence of catalytic amounts of CuCN and PdCl2(PPh3)(2) or [(p-MeOC6H4)(3)P](4)Pd affords 2-aryl substituted amines in modest to good yields. The yields can be improved by use of softer ligands such as AsPh3 and SbPh3 or by use of bis(diphenylphosphino)ferrocene (dppf). Coupled products are obtained with electron-rich aryl iodides (XArI, X = Me, OMe), and the reaction fails with electron-poor aryl iodides (XArI, X = NO2, CO2Li). Treatment of the (alpha-aminoalkyl)lithium reagents with vinyl iodides and Pd(0)/dppf/CuCN afforded the coupling products in low to modest yields.