(E)-butyl 3-(6-methoxynaphthalen-2-yl)acrylate | 131077-96-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-butyl 3-(6-methoxynaphthalen-2-yl)acrylate
• 英文别名: butyl (E)-3-(6-methoxynaphthalen-2-yl)prop-2-enoate
• CAS: 131077-96-8
• 化学式: C₁₈H₂₀O₃
• 分子量: 284.355
• InChiKey: RLSBCINFGATEIA-UXBLZVDNSA-N

物化性质

• 沸点：
  432.6±20.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙烯酸丁酯 、 2-溴-6-甲氧基萘 在 palladium diacetate N-甲基吡咯烷酮 、 sodium acetate 作用下， 反应 1.0h， 生成 (E)-butyl 3-(6-methoxynaphthalen-2-yl)acrylate
  参考文献：
  名称：

  不含顺势配体的钯在heck反应中作为催化剂。与palladacycle的比较。

  摘要：

  [反应：见正文]只要催化剂的量保持在0.01至0.1 mol％之间，则无配体的Pd（OAc）（2）可以用作芳基溴化物的Heck反应中的催化剂。在较高浓度下会形成钯黑，反应会停止。实际的催化剂是单体的。在芳基溴化物的Heck反应中，Palladacycles仅充当不含配体的钯的来源。

  DOI：

  10.1021/ol035184b

文献信息

• General Olefin Synthesis by the Palladium‐Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective NC Activation
  作者：Guangrong Meng、Michal Szostak

  DOI：10.1002/anie.201507776

  日期：2015.11.23

  Metal‐catalyzed reactions of amides proceeding via metal insertion into the NCO bond are severely underdeveloped due to resonance stabilization of the amide bond. Herein we report the first Heck reaction of amides proceeding via highly chemoselective NCO cleavage catalyzed by Pd0 utilizing amide bond ground‐state destabilization. Conceptually, this transformation provides access to a myriad of metal‐catalyzed

  由于酰胺键的共振稳定作用，通过金属插入NCO键进行的酰胺的金属催化反应严重不足。本文中，我们报道了酰胺的第一个Heck反应，该过程通过Pd 0催化的高化学选择性N ization CO裂解，利用酰胺键基态去稳定作用进行。从概念上讲，这种转变可通过金属插入/脱羰作用使酰胺进行多种金属催化的转变。
• Palladium-catalyzed Heck reactions promoted by limonene-derived bicyclic phosphines
  作者：Boitumelo Setati、Paseka Thendo Moshapo、Cedric Wahl Holzapfel、Munaka Christopher Maumela

  DOI：10.1080/00397911.2022.2093646

  日期：2022.7.18

  Abstract Tertiary bicyclic phosphines derived from (R)-(+)-limonene provided efficient palladium catalysts for Heck cross-coupling reactions. Overall, high yields of the desired aryl alkenes products were obtained for cross-coupling of sterically and electronically diverse substrates. The efficiency of the catalysts was further demonstrated in the synthesis of commercial ketones, such as raspberry

  摘要 衍生自 (R)-(+)-柠檬烯的叔双环膦为 Heck 交叉偶联反应提供了高效的钯催化剂。总体而言，获得了所需芳基烯烃产物的高产率，用于空间和电子多样化底物的交叉偶联。在商业酮的合成中进一步证明了催化剂的效率，例如覆盆子酮及其衍生物。
• Neutral vs anionic palladium iodide-catalyzed carbonylation of terminal arylacetylenes
  作者：Michele Queirolo、Adriano Vezzani、Raffaella Mancuso、Bartolo Gabriele、Mirco Costa、Nicola Della Ca’

  DOI：10.1016/j.molcata.2014.11.028

  日期：2015.3

  The hydroalkoxycarbonylation of terminal arylacetylenes can be carried out in an easy one-step synthesis through the use of PdI2 or PdI2/KI as catalytic systems under non-oxidative conditions, without other ligands and in the absence of added acids. Going from non-polar to polar reaction media, we have noticed a dramatic change in the chemoselectivity of the reaction with prevailing formation of alpha-,beta-unsaturated esters, in the former case, and a mixture of oxidative (maleic esters derivatives) and reductive (mainly unsaturated lactones) carbonylation products in comparable amount, in the latter case. The origin of this behavior can be explained with the different active species at work changing the reaction media: neutral palladium species in non-polar media and ionic palladium species in polar media. (C) 2014 Elsevier B.V. All rights reserved.
• Miura, Masahiro; Hashimoto, Hideo; Itoh, Kenji, Journal of the Chemical Society. Perkin transactions I, 1990, # 8, p. 2207 - 2211
  作者：Miura, Masahiro、Hashimoto, Hideo、Itoh, Kenji、Nomura, Masakatsu

  DOI：——

  日期：——
• Heck reaction in ionic liquids catalyzed by a Pd–benzothiazole carbene complex
  作者：Vincenzo Calò、Angelo Nacci、Luigi Lopez、Nicola Mannarini

  DOI：10.1016/s0040-4039(00)01592-6

  日期：2000.11

  A Pd-catalyst with benzothiazole carbene ligands allows, in ionic liquids as solvent, very fast and efficient reactions of haloaromatics with alkenes. (C) 2000 Elsevier Science Ltd. All rights reserved.