tert-butyl 3,3-bis(4-methoxyphenyl)acrylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl 3,3-bis(4-methoxyphenyl)acrylate
• 英文别名: Tert-butyl 3,3-bis(4-methoxyphenyl)prop-2-enoate
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: NOUJCMHTIMIQBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 3,3-bis(4-methoxyphenyl)acrylate 在 palladium on carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以85%的产率得到tert-butyl 3,3-bis(4-methoxyphenyl)propanoate
  参考文献：
  名称：

  Pd–arylurea complexes for the Heck arylation of crotonic and cinnamic substrates

  摘要：

  A catalyst consisting of the 1:2 complex of Pd(OAc)(2) (1 mol %) with N-(4-carbethoxy)-phenylurea promotes the Heck arylation of a range of crotonic and cinnamic substrates, including aldehydes, ketones, esters, and nitriles, with electron-rich-but not electron-deficient-aryl iodides. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.077
• 作为产物：
  描述：

  4-碘苯甲醚 、 tert-butyl (E)-3-(4-methoxyphenyl)prop-2-enoate 在 N-(4-carbethoxyphenyl)urea 、 palladium diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 16.0h， 以54%的产率得到tert-butyl 3,3-bis(4-methoxyphenyl)acrylate
  参考文献：
  名称：

  Pd–arylurea complexes for the Heck arylation of crotonic and cinnamic substrates

  摘要：

  A catalyst consisting of the 1:2 complex of Pd(OAc)(2) (1 mol %) with N-(4-carbethoxy)-phenylurea promotes the Heck arylation of a range of crotonic and cinnamic substrates, including aldehydes, ketones, esters, and nitriles, with electron-rich-but not electron-deficient-aryl iodides. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.077

文献信息

• Organocatalytic deprotonative functionalization of C(sp2)–H and C(sp3)–H bonds using in situ generated onium amide bases
  作者：Kiyofumi Inamoto、Hitomi Okawa、Hiroshi Taneda、Maomi Sato、Yutaro Hirono、Misato Yonemoto、Shoko Kikkawa、Yoshinori Kondo

  DOI：10.1039/c2cc35701a

  日期：——

  Onium amides, generated in situ from the combination of aminosilanes and onium fluorides (R(4)PF, R(4)NF), are employed for the first time as bases for catalytic deprotonative functionalization of C(sp(2))-H and activated C(sp(3))-H bonds under mild conditions.

  由氨基硅烷和氟化鎓（R（4）PF，R（4）NF）的组合就地生成的鎓酰胺首次用作C（sp（2））-H催化去质子功能化的基础和活化的C（sp（3））-H键在温和的条件下。
• Mono- and β,β-Double-Heck Reactions of α,β-Unsaturated Carbonyl Compounds in Aqueous Media
  作者：Luis Botella、Carmen Nájera

  DOI：10.1021/jo0502551

  日期：2005.5.1

  and nitrile. β,β-Diarylation of unsubstituted α,β-unsaturated carbonyl compounds can be controlled by using higher loading of the palladacycle and can be performed in refluxing water for aryl iodides, whereas DMA must be used for aryl bromides. Microwave irradiation can be used in the monoarylation of tert-butyl acrylate with aryl iodides in water or the coupling between ethyl cinnamate and aryl bromides

  在无磷条件下且在无膦存在下，由对羟基苯乙酮肟肟的巴拉达环或乙酸钯（II）催化的水性介质中缺电子烯烃的单和β，β-二芳基化的最佳反应条件描述了以二环己基）甲胺为碱。未取代和取代的α，β-不饱和羰基化合物的区域选择性单芳基化反应在120°C的水中与芳基碘化物进行。N，N-二甲基乙酰胺（DMA）水溶液，四正以丁基丁基溴化铵（TBAB）为添加剂，以palladacycle为催化剂是与芳基溴化物偶联的最有效条件，在巴豆酸酯和衣康酸酯的芳基化中也获得了良好的立体选择性，而肉桂酸酯衍生物的立体选择性较低，但肉桂酸和腈。未取代的α，β-不饱和羰基化合物的β，β-二芳基化反应可以通过使用较高的palladacycle来控制，并且可以在回流水中进行芳基碘化物的操作，而DMA必须用于芳基溴化物。微波辐射可用于丙烯酸叔丁酯与芳基碘化物在水中的单芳基化，或肉桂酸乙酯与DMA水溶液中的芳基溴化物之间的偶合。
• N-heterocycle carbene (NHC)-ligated cyclopalladated N,N-dimethylbenzylamine: a highly active, practical and versatile catalyst for the Heck–Mizoroki reaction
  作者：Guang-Rong Peh、Eric Assen B. Kantchev、Chi Zhang、Jackie Y. Ying

  DOI：10.1039/b821892g

  日期：——

  NHC-Pd catalyst, a triflate was coupled with diverse acrylate derivatives (nitrile, tert-butyl ester and amides) and styrene derivatives. The use of excess (>2 equiv.) of the aryl bromide and tert-butyl acrylate leads to mixture of tert-butyl β,β-diarylacrylate and tert-butyl cinnamate derivatives depending on the substitution pattern of the aryl bromide. Electron rich m- and p-substituted arylbromides

  催化剂的发展不仅促进了催化方案在学术和工业实验室中的广泛传播，该催化剂不仅具有高活性，而且还易于使用，对湿气，空气和长期储存稳定，易于大规模制备。在本文中，我们描述了由环钯N，N-二甲基苄胺（dmba）与N杂环卡宾1,3-双（甲磺酰基）咪唑-2-亚基（IMes）连接而介导的Heck-Mizoroki反应的方案标准。可以通过三组分，顺序，一锅法反应制得约100 g规模的预催化剂。N，N-二甲基苄胺，PdCl 2和IMes·HCl回流乙腈在空气中存在K 2 CO 3的情况下。这种单组分催化剂对空气，湿气和长期储存稳定，并且可以方便地作为储备溶液分配到NMP中。它介导0.1-2 mol％范围的试剂级NMP中的一系列芳基和杂芳基溴的Heck-Mizoroki反应，而无需严格的无水技术或手套箱，甚至在空气中也具有活性。该催化剂能够实现很高的催化活性（TON高达5.22×10 5），用于偶联失活的芳基溴化物，对溴苯甲醚，以t
• Selective reactivity of electron-rich aryl iodides in the Heck arylation of disubstituted alkenes catalyzed by palladium–arylurea complexes
  作者：Matthew R. Smith、Young Jin Jang、Jung Yun Kim、Marco A. Ciufolini

  DOI：10.1016/j.tet.2013.09.019

  日期：2013.11

  A catalyst consisting of 1 mol % of the 1:2 complex of Pd(OAc)(2) with N-(4-carbethoxyphenyl)urea promotes the Heck arylation of 2- or 3-substituted, conjugated esters, nitriles, aldehydes, and ketones (an uncharacteristically broad range of substrates), but only with electron-rich aryl iodides (an uncharacteristically narrow range of halides). (C) 2013 Elsevier Ltd. All rights reserved.
• Controlled mono and double Heck reactions in water catalyzed by an oxime-derived palladacycle
  作者：Luis Botella、Carmen Nájera

  DOI：10.1016/j.tetlet.2004.01.024

  日期：2004.2

  The mono and beta,beta-diarylation of alpha,beta-unsaturated carbonyl compounds with electron-deficient and electron-rich aromatic iodides in water is described. These reactions are catalyzed by the p-hydroxyacetophenone oxime-derived palladacycle 1 by controlling the stoichiometry of the aryl iodide and the alkene as well as the loading of the palladium catalyst. This one-pot protocol is performed in refluxing water and (dicyclohexyl)methylamine as base under thermal or microwave conditions and in the absence of an inert atmosphere. (C) 2004 Elsevier Ltd. All rights reserved.