tert-butyl 1-naphthoate | 66821-79-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl 1-naphthoate
• 英文别名: tert-Butyl naphthalene-1-carboxylate
• CAS: 66821-79-2
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: XXKNPBDPZLPLFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl 1-naphthoate 在 氨 、 水 、 sodium 作用下， 以 四氢呋喃 为溶剂， 以42%的产率得到tert-butyl 1,4-dihydro-1-naphthoate
  参考文献：
  名称：

  Metal-ammonia ring reduction of aromatic carboxylic acid esters

  摘要：

  DOI：

  10.1021/jo00183a014
• 作为产物：
  描述：

  1-(azido(tert-butylperoxy)methyl)naphthalene 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙酸乙酯 为溶剂， 反应 0.25h， 以86%的产率得到tert-butyl 1-naphthoate
  参考文献：
  名称：

  Synthesis and Asymmetric Resolution of α-Azido-peroxides

  摘要：

  An unprecedented synthesis of alpha-azido-peroxides has been developed using an FeCl3-catalyst starting from carbonyl, TMS-azide, and hydroperoxide. Further, a base promoted decomposition of synthesized secondary alpha-azido-peroxides to provide the corresponding tert-butyl esters has been disclosed. Finally, an asymmetric kinetic resolution of such alpha-azido-peroxides has also been developed to provide chiral a-azido-peroxides in excellent enantiopurity.

  DOI：

  10.1021/ol401443a

文献信息

• Copper-catalyzed oxidative esterification of aldehydes with dialkyl peroxides: efficient synthesis of esters of tertiary alcohols
  作者：Yefeng Zhu、Yunyang Wei

  DOI：10.1039/c3ra40246k

  日期：——

  Copper-catalyzed oxidative esterification of aldehydes with dialkyl peroxides has been developed. This protocol affords a novel approach for the synthesis of carboxylic esters of tertiary alcohols under mild conditions. Depending on the catalyst system, a variety of tertiary esters were produced in good to excellent yields.

  已经开发了铜催化的醛与二烷基过氧化物的氧化酯化反应。该方案提供了一种在温和条件下合成叔醇羧酸酯的新方法。根据催化剂体系的不同，可以产生高至优收率的各种叔酯。
• Silver/manganese dioxide nanorod catalyzed hydrogen-borrowing reactions and <i>tert</i>-butyl ester synthesis
  作者：Huanhuan Luo、Yike Yang、Bobin Yang、Zhaojun Xu、Dawei Wang

  DOI：10.1177/1747519821989963

  日期：2021.7

  hydrogen-borrowing reactions in high yields and are also effective for the synthesis of tert-butyl esters from aryl cyanides and tert-butyl hydroperoxide in a short period of time. Mechanistic experiments revealed that this catalytic system acts as a Lewis acid in hydrogen-borrowing reactions, while the synthesis of tert-butyl esters occurs through a radical pathway. This is the first report on the excellent catalytic

  合成了银/二氧化锰（[受电子邮件保护] 2）纳米棒，并通过扫描电子显微镜，透射电子显微镜，能量色散X射线光谱，X射线粉末衍射和X射线光电子光谱对其进行了表征。发现[受电子邮件保护的] 2个纳米棒可以高产率地实现氢借入反应，并且还可以在短时间内有效地由芳基氰化物和叔丁基氢过氧化物合成叔丁基酯。机理实验表明，该催化体系在氢借位反应中起路易斯酸的作用，而叔丁基的合成丁酯通过自由基途径发生。这是关于[电子邮件保护的] 2纳米棒作为催化剂的出色催化活性的第一份报告。
• Metal-free radical aromatic carbonylations mediated by weak bases
  作者：Denis Koziakov、Axel Jacobi von Wangelin

  DOI：10.1039/c7ob01572k

  日期：——

  We report a new method of metal-free alkoxycarbonylation. This reaction involves the generation of aryl radicals from arenediazonium salts by a very weak base (HCO2Na) under mild conditions. Subsequent radical trapping with carbon monoxide and alcohols gives alkyl benzoates. The conditions (metal-free, 1 equiv. base, MeCN, r.t., 3 h) tolerate various functional groups (I, Br, Cl, CF3, SF5, NO2, ester)

  我们报告了一种新的无金属烷氧基羰基化方法。该反应涉及在温和的条件下通过非常弱的碱（HCO 2 Na）由槟榔鎓盐生成芳基。随后用一氧化碳和醇进行自由基捕获，得到苯甲酸烷基酯。条件（无金属，1当量碱，MeCN，rt，3 h）可耐受各种官能团（I，Br，Cl，CF 3，SF 5，NO 2，酯）。机理研究表明自由基芳族取代机理的运行。
• New Mixed Li/Mg and Li/Mg/Zn Amides for the Chemoselective Metallation of Arenes and Heteroarenes
  作者：Christoph J. Rohbogner、Stefan H. Wunderlich、Giuliano C. Clososki、Paul Knochel

  DOI：10.1002/ejoc.200801277

  日期：2009.4

  New mixed Li/Mg and Li/Mg/Zn amides have been synthesized starting from readily prepared secondary amines. They allow a highly chemoselective directed magnesiation or zincation of various polyfunctional aromatics and heteroaromatics. The kinetic basicity, solubility and stability of these new bases have been compared with those of the corresponding 2,2,6,6-tetramethylpiperamide-derived bases.(© Wiley-VCH

  新的混合 Li/Mg 和 Li/Mg/Zn 酰胺已从易于制备的仲胺开始合成。它们允许各种多官能芳烃和杂芳烃的高度化学选择性定向镁化或锌化。这些新碱的动力学碱度、溶解度和稳定性与相应的 2,2,6,6-四甲基哌酰胺衍生碱进行了比较。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009 )
• Aluminum Bases for the Highly Chemoselective Preparation of Aryl and Heteroaryl Aluminum Compounds
  作者：Stefan H. Wunderlich、Paul Knochel

  DOI：10.1002/anie.200804966

  日期：2009.2.9

  Selective CH activation with a series of neutral aluminum trisamide bases led to a wide range of polyfunctional aryl and heteroaryl aluminum reagents. Ester and cyano groups are stable under the reaction conditions for this direct alumination, and donor oxygen substituents are efficient directing groups. High metalation regioselectivities were observed with O,S and N,S heterocycles (see example).

  选择性Ç  ħ激活了一系列导致了宽范围的多官能芳基和杂芳基铝试剂的中性铝trisamide碱基。酯基和氰基在该直接铝化反应的反应条件下是稳定的，供体氧取代基是有效的导向基团。用O，S和N，S杂环观察到高的金属化区域选择性（参见实施例）。