tert-butyl (E)-2-styrylpiperidine-1-carboxylate | 1221972-12-8

• 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 (E)-2-styrylpiperidine-1-carboxylate
• 英文别名: tert-butyl 2-[(E)-styryl]piperidine-1-carboxylate；tert-butyl 2-[(E)-2-phenylethenyl]piperidine-1-carboxylate
• CAS: 1221972-12-8
• 化学式: C₁₈H₂₅NO₂
• 分子量: 287.402
• InChiKey: VQLPMQJOAZCUPM-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  acetic acid (E)-7-tert-butoxycarbonylamino-1-phenyl-hept-2-enyl ester 在 iron(III) chloride hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以72%的产率得到tert-butyl (E)-2-styrylpiperidine-1-carboxylate
  参考文献：
  名称：

  FeCl₃-Catalyzed Highly Diastereoselective Synthesis of Substituted Piperidines and Tetrahydropyrans

  摘要：

  The eco-friendly and highly diastereoselective synthesis of substituted cis-2,6-piperidines and cis-2,6-tetrahydropyrans is described. The key step of this method is the iron-catalyzed thermodynamic equilibration of 2-alkenyl 6-substituted piperidines and 2-alkenyl 6-substituted tetrahydropyrans allowing the isolation of enriched mixtures of the most stable cis-isomers.

  DOI：

  10.1021/ol100422d

文献信息

• Selective Syntheses of <i>Z</i>-Alkenes via Photocatalyzed Decarboxylative Coupling of <i>N</i>-Hydroxyphthalimide Esters with Terminal Arylalkynes
  作者：Guo-Li Dai、Shu-Zhen Lai、Zhuangzhu Luo、Zhen-Yu Tang

  DOI：10.1021/acs.orglett.9b00558

  日期：2019.4.5

  A novel, efficient Z-alkene synthesis via photocatalyzed decarboxylative couplings between terminal aryl alkynes and alkyl N-hydroxyphthalimide (NHPI) esters, which are derived from aliphatic carboxylic acids, is described. A wide range of primary, secondary, and tertiary carboxylates as well as α-amino acid and α-oxyacid-derived esters were employed as suitable substrates. The mild reaction conditions

  描述了通过末端芳基炔烃和衍生自脂族羧酸的烷基N-羟基邻苯二甲酰亚胺（NHPI）酯之间的光催化脱羧偶联的新颖，有效的Z-烯烃合成。各种各样的伯，仲和叔羧酸盐以及α-氨基酸和α-含氧酸衍生的酯被用作合适的底物。温和的反应条件，广泛的底物范围，官能团耐受性和操作简便性使得该脱羧偶联反应成为有机合成中的重要方法。
• Vinyl Sulfonium Salts as the Radical Acceptor for Metal-Free Decarboxylative Alkenylation
  作者：Yu-Lan Zhang、Lei Yang、Jie Wu、Chunyin Zhu、Peng Wang

  DOI：10.1021/acs.orglett.0c03074

  日期：2020.10.2

  Vinyl sulfonium salts typically act as an electrophilic Michael acceptor, thus initiating many tandem cyclization reactions. Herein, we disclosed the novel reactivity of vinyl sulfonium salts as a radical acceptor. Using redox-active ester as an alkyl radical precursor, metal-free decarboxylative alkenylation with vinyl sulfonium salts was realized using eosin Y as a photocatalyst. This process features

  乙烯基sulf盐通常充当亲电的迈克尔受体，因此引发许多串联环化反应。在这里，我们公开了乙烯基sulf盐作为自由基受体的新型反应性。使用氧化还原活性酯作为烷基自由基前体，使用曙红Y作为光催化剂实现了带有乙烯基sulf盐的无金属脱羧烯基化。该方法具有广泛的底物范围，并能耐受多种伯，仲，叔羧酸。
• [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
• Photoredox α-Vinylation of α-Amino Acids and <i>N</i>-Aryl Amines
  作者：Adam Noble、David W. C. MacMillan

  DOI：10.1021/ja506094d

  日期：2014.8.20

  union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C–H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural

  已开发出一种新的偶联方案，允许乙烯基砜与光氧化还原生成的 α-氨基自由基结合，以提供广泛多样的烯丙胺。N-芳基叔胺的直接 C-H 乙烯基化以及 N-Boc α-氨基酸的脱羧乙烯基化以高产率和出色的烯烃几何控制进行。这种新的烯丙胺形成反应的效用已通过几种天然产物和许多已建立的药效团的合成得到证明。
• Decarboxylative Hydroalkylation of Alkynes via Dual Copper-Photoredox Catalysis
  作者：Marco M. Mastandrea、Santiago Cañellas、Xisco Caldentey、Miquel A. Pericàs

  DOI：10.1021/acscatal.0c01742

  日期：2020.6.5

  base. The developed methodology has been applied to the stereoselective coupling of primary, secondary, and tertiary alkyl radicals with (hetero)aromatic terminal alkynes. As an additional practicality, similar reaction conditions allowed for the use of aromatic amines as radical precursors in a cross dehydrogenative coupling for the direct vinylation of inactivated C–H bonds.

  已经开发了用于从羧酸和炔烃合成各种烯丙基胺和醚的光氧化还原策略。这种方法依赖于通过炔基铜中间体的形成和光激发对末端炔烃基态电子特性的扰动。该过程通过铜和有机光氧化还原的协同催化进行，并且可以立体发散的方式进行。因此，系统的多变量HTE筛选显示，通过选择合适的配体和碱基组合，可以引起立体化学结果的改变。所开发的方法已应用于伯，仲和叔烷基与（杂）芳族末端炔的立体选择性偶联。另外，