N-(tert-butoxycarbonyl)-N-(4-methoxybenzyl)-4-amino-1-butyne | 398476-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(tert-butoxycarbonyl)-N-(4-methoxybenzyl)-4-amino-1-butyne
• 英文别名: tert-butyl N-but-3-ynyl-N-[(4-methoxyphenyl)methyl]carbamate
• CAS: 398476-24-9
• 化学式: C₁₇H₂₃NO₃
• 分子量: 289.375
• InChiKey: UIQIIMJSOQCHTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  N-(tert-butoxycarbonyl)-N-(4-methoxybenzyl)-4-amino-1-butyne 在 三苯基膦氯金 silver hexafluoroantimonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以75%的产率得到N-(4-methoxybenzyl)-6-methylidene-1,3-oxazin-2-one
  参考文献：
  名称：

  Gold-Catalyzed Synthesis of Alkylidene 2-Oxazolidinones and 1,3-Oxazin-2-ones

  摘要：

  N-Boc-protected alkynylamines are converted into the corresponding alkylidene 2-oxazolidinones or 2-oxazinones under very mild reaction conditions in the presence of 1-5 mol% of a cationic Au(I) complex. The scope of the reaction is very general, providing the cyclic carbamates in high yield regardless of the substitution at nitrogen and alkyne terminus.

  DOI：

  10.1021/jo060520y
• 作为产物：
  描述：

  (+/-)-1-(4-methoxybenzyl)azetidine-2-carbonitrile 在 叠氮基三甲基硅烷 、 二正丁基氧化锡 作用下， 以 甲苯 为溶剂， 反应 99.0h， 生成 N-(tert-butoxycarbonyl)-N-(4-methoxybenzyl)-4-amino-1-butyne
  参考文献：
  名称：

  Synthesis of homopropargylamines from 2-cyanoazetidines

  摘要：

  从α-氨基腈中产生乙烯基碳烯是合成同异丙炔胺的新方法的基础。

  DOI：

  10.1039/c6cc05713f

文献信息

• Enantio- and diastereoselective palladium catalysed arylative and vinylative allene carbocyclisation cascades
  作者：Meiling Li、Alison Hawkins、David M. Barber、Patrick Bultinck、Wouter Herrebout、Darren J. Dixon

  DOI：10.1039/c3cc42079e

  日期：——

  The enantioselective synthesis of heavily decorated spirolactams has been accomplished via an arylative or vinylative allene carbocyclisation cascade. Mediated by silver phosphate, a range of allene-linked pro-nucleophiles and aryl or vinyl iodides were reacted in the presence of catalytic Pd(OAc)2 and chiral bis(oxazoline) ligands to afford the spirolactam products in good yields and high enantio-

  大量装饰的螺内酰胺的对映选择性合成是通过芳基或乙烯基化的异戊烯碳环化级联反应完成的。在磷酸银的介导下，在催化性Pd（OAc）2和手性双（恶唑啉）配体的存在下，使一系列与烯丙基连接的亲核亲核试剂和芳基或乙烯基碘反应，从而以高收率和高对映体产率提供螺内酰胺产品。和非对映选择性。
• Indenylidene Complexes of Ruthenium: Optimized Synthesis, Structure Elucidation, and Performance as Catalysts for Olefin Metathesis—Application to the Synthesis of the ADE-Ring System of Nakadomarin A
  作者：Alois Fürstner、Oliver Guth、Arno Düffels、Günter Seidel、Monika Liebl、Barbara Gabor、Richard Mynott

  DOI：10.1002/1521-3765(20011119)7:22<4811::aid-chem4811>3.0.co;2-p

  日期：2001.11.19

  complex 3 is as good as or even superior to the classical Grubbs carbene 1 in terms of yield, reaction rate, and tolerance towards polar functional groups. Complex 3 turns out to be the catalyst of choice for the synthesis of the enantiopure core segment 77 of the marine alkaloid nakadomarin A 60 comprising the ADE rings of this target. Together with a series of other examples, this particular application

  描述了钌苯基茚基亚烷基络合物3的优化且大规模适用的合成，其使用市售的二苯基炔丙醇5作为稳定且方便的卡宾源。通过对该化合物的NMR光谱进行全面分析，排除了先前对该化合物的实际结构的歧义。闭环复分解（RCM）反应的一系列应用表明，在收率，反应速率和对极性官能团的耐受性方面，配合物3与经典的Grubbs卡宾1一样好，甚至更好。络合物3被证明是用于合成包含该靶标的ADE环的海洋生物碱中型抗癌蛋白A 60的对映纯核心链段77的选择催化剂。再加上一系列其他示例，该特定的应用说明了催化剂3特别适合于通过RCM环化中型环。通往nakadomarin A的其他关键步骤是高度选择性的分子内迈克尔加成，将四元中心置于A和D环的交界处，以及醛73与CH2I2，Ti（OiPr）4和活性锌粉的Takai-Nozaki烯化反应。
• Microwave-Mediated Nickel-Catalyzed Cyclotrimerization Reactions:  Total Synthesis of Illudinine
  作者：Jesse A. Teske、Alexander Deiters

  DOI：10.1021/jo7020955

  日期：2008.1.1

  [GRAPHICS]Rapid and efficient [2 + 2 + 2] cyclotrimerization reactions were discovered through the application of microwave irradiation in conjunction with a Ni(CO)(2)(PPh3)(2) catalyst. This enables the facile construction of highly substituted indane, isoindoline, and tetraline core structures. The developed microwave-mediated Ni-catalyzed cyclotrimerization reaction was employed as the key step in a concise synthesis of the isoquinoline natural product illudinine. This represents the first example of a Ni-catalyzed cyclotrimerization reaction in total synthesis.
• Synthesis of homopropargylamines from 2-cyanoazetidines
  作者：P. Quinodoz、K. Wright、B. Drouillat、O. David、J. Marrot、F. Couty

  DOI：10.1039/c6cc05713f

  日期：——

  Mild generation of vinylidene carbene from α-amino nitrile is the basis of a new synthesis of homopropargylamines.

  从α-氨基腈中产生乙烯基碳烯是合成同异丙炔胺的新方法的基础。
• Gold-Catalyzed Synthesis of Alkylidene 2-Oxazolidinones and 1,3-Oxazin-2-ones
  作者：Rocío Robles-Machín、Javier Adrio、Juan Carlos Carretero

  DOI：10.1021/jo060520y

  日期：2006.6.1

  N-Boc-protected alkynylamines are converted into the corresponding alkylidene 2-oxazolidinones or 2-oxazinones under very mild reaction conditions in the presence of 1-5 mol% of a cationic Au(I) complex. The scope of the reaction is very general, providing the cyclic carbamates in high yield regardless of the substitution at nitrogen and alkyne terminus.