(Z)-tert-butyl (2-(pyridin-2-yl)vinyl)carbamate | 1440754-09-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (Z)-tert-butyl (2-(pyridin-2-yl)vinyl)carbamate
• 英文别名: tert-butyl N-[(Z)-2-pyridin-2-ylethenyl]carbamate
• CAS: 1440754-09-5
• 化学式: C₁₂H₁₆N₂O₂
• 分子量: 220.271
• InChiKey: IPCYUILJRSLKCW-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-{[(2-甲基-2-丙基)氧基]羰基}-3-(2-吡啶基)丙氨酸 在 9-mesityl-2,7-dimethyl-10-phenylacridin-10-ium tetrafluoroborate 、 copper diacetate 作用下， 以 乙腈 为溶剂， 反应 14.0h， 以47%的产率得到(Z)-tert-butyl (2-(pyridin-2-yl)vinyl)carbamate
  参考文献：
  名称：

  光诱导的高知脱羧消除法，用于从N-酰基氨基酸合成酰胺和烯胺。

  摘要：

  通过有机光氧化还原催化剂和乙酸铜作为末端氧化剂的组合，已经实现了脱除N-酰基氨基酸的脱羧反应，从而提供了酰胺和烯氨基甲酸酯结构单元。这种操作简单的方法利用了廉价且容易获得的试剂，而没有将羧酸预先活化。现在可以直接从N-酰基氨基酸中获得酰胺和烯氨基甲酸酯，因此提高了Kochi羧酸的氧化脱羧的效用。

  DOI：

  10.1021/acs.joc.9b00167

文献信息

• Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective <i>N</i>-<i>tert</i>-butyloxycarbonylation of amines
  作者：Ajit P. Ingale、Dnyaneshwar N. Garad、Dattatraya Ukale、Nitin M. Thorat、Sandeep V. Shinde

  DOI：10.1080/00397911.2021.1994998

  日期：2021.12.17

  approach has been described for the chemoselective N-tert-butyloxycarbonylation of amines under solvent-free conditions at ambient temperature. The demonstrated approach has been applicable for the N-Boc protection of variety of aliphatic, aryl, heteroaryl amines. The chemoselective protection of amino group occurs in chiral amines and amino alcohol without racemization in high yield. Thiamin hydrochloride

  摘要 盐酸硫胺素促进高效和生态友好的方法已被描述的用于化学选择性Ñ -叔在环境温度下在无溶剂条件下与胺的-butyloxycarbonylation。所证明的方法已适用于各种脂肪族、芳基、杂芳基胺的N- Boc 保护。氨基的化学选择性保护发生在手性胺和氨基醇中，没有高产率的外消旋化。盐酸硫胺素稳定、经济、易处理、环保。
• [RhCp*Cl₂]₂-Catalyzed Directed <i>N</i>-Boc Amidation of Arenes “on Water”
  作者：Md Ashif Ali、Xiayin Yao、Hao Sun、Hongjian Lu

  DOI：10.1021/acs.orglett.5b00392

  日期：2015.3.20

  Rhodium(III) catalysis on water is effective for directed C-H amidation of arenes. The catalytic process is promoted by OH groups present on the hydrophobic water surface and is inefficient in all (most) common organic solvents investigated so far. In the presence of easily prepared tert-butyl 2,4-dinitrophenoxycarbamate, a new and stable nitrene source, the on water reaction can efficiently provide the desired N-Boc-aminated products with good functional group tolerance.
• Rh[III]-Catalyzed C–H Amidation Using Aroyloxycarbamates To Give <i>N</i>-Boc Protected Arylamines
  作者：Christoph Grohmann、Honggen Wang、Frank Glorius

  DOI：10.1021/ol401209f

  日期：2013.6.21

  The Rh(III)-catalyzed amidation of C(sp(2))-H bonds by the use of electron-deficient aroyloxycarbamates as efficient electrophilic amidation partners is reported. The reaction proceeded under mild conditions with broad functional group tolerance, and pyridine and O-methyl hydroxamic acids serve as efficient directing groups, giving access to valuable N-Boc protected arylamines (also Fmoc and Cbz). Preliminary mechanistic experiments are discussed.