Ethyl 3-(9-Anthryl)prop-2-enoate | 236429-70-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Ethyl 3-(9-Anthryl)prop-2-enoate
• 英文别名: 3-(9-anthracenyl)acrylic acid ethyl ester；ethyl 3-(E)-(anthracen-9-yl)prop-2-enoate；ethyl (E)-3-(anthracen-9-yl)acrylate；3t-[9]anthryl-acrylic acid ethyl ester；3t-[9]Anthryl-acrylsaeure-aethylester；ethyl (E)-3-anthracen-9-ylprop-2-enoate
• CAS: 236429-70-2
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: JVJXQLSMWPXJBD-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  Ethyl 3-(9-Anthryl)prop-2-enoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 3-(9-Anthryl)prop-2-enoic Acid
  参考文献：
  名称：

  Effenberger, Franz; Wonner, Johann, Chemische Berichte, 1992, vol. 125, # 11, p. 2583 - 2590

  摘要：

  DOI：
• 作为产物：
  描述：

  9-蒽甲醛 、 乙氧甲酰基亚甲基三苯基膦 以 二氯甲烷 为溶剂， 以90%的产率得到Ethyl 3-(9-Anthryl)prop-2-enoate
  参考文献：
  名称：

  通过立即蒸发溶剂加快有机反应的速率。

  摘要：

  由于显着提高了反应物之间的分子与分子之间的接触，可通过立即蒸发溶剂来加速几种类型的有机反应。

  DOI：

  10.1039/b609567d

文献信息

• Systematic Study on the Catalytic Arsa‐Wittig Reaction
  作者：Ryoto Inaba、Ikuo Kawashima、Toshiki Fujii、Takashi Yumura、Hiroaki Imoto、Kensuke Naka

  DOI：10.1002/chem.202002792

  日期：2020.10.21

  Efficient catalytic arsa‐Wittig reactions have been developed by using 1‐phenylarsolane as a catalyst. A wide array of aldehydes was converted to the corresponding olefins in high yields with moderate to excellent E stereoselectivity in the presence of a catalytic amount of 1‐phenylarsolane. Moreover, density functional theory calculations were carried out to afford insight into the E/Z selectivity

  通过使用1-苯基芳烷作为催化剂，开发了有效的arsa-Wittig催化反应。在催化量的1-苯基芳烷存在下，大量醛以高收率转化为相应的烯烃，同时具有中等至优异的E立体选择性。此外，进行了密度泛函理论计算，以深入了解E / Z选择性。
• Rate acceleration of organic reaction by immediate solvent evaporation
  作者：Akihiro Orita、Genta Uehara、Kai Miwa、Junzo Otera

  DOI：10.1039/b609567d

  日期：——

  Several types of organic reactions were accelerated by immediate evaporation of solvents because of remarkable enhancement of molecule-to-molecule contacts between reactants.

  由于显着提高了反应物之间的分子与分子之间的接触，可通过立即蒸发溶剂来加速几种类型的有机反应。
• An enhanced stereoselective synthesis of α,β-unsaturated esters through the Horner–Wadsworth–Emmons reaction in deep eutectic solvents
  作者：Andrea Nicola Paparella、Margherita Stallone、Mara Pulpito、Filippo Maria Perna、Vito Capriati、Paola Vitale

  DOI：10.1039/d3ob02083e

  日期：——

  A new scalable synthesis of (E)-α,β-unsaturated esters has been developed using protic, non-toxic, and biodegradable deep eutectic solvents through the Horner–Wadsworth–Emmons reaction between triethyl phosphonates and (hetero)aromatic carbonyl compounds, encompassing electron-withdrawing and electron-donating groups. Stereoselective preparation of disubstituted or trisubstituted ethyl cinnamate derivatives

  通过膦酸三乙酯和（杂）芳族羰基化合物之间的霍纳-沃兹沃斯-埃蒙斯反应，使用质子、无毒且可生物降解的低共熔溶剂开发了一种新的可规模合成（ E ）-α,β-不饱和酯，包括吸电子基团和给电子基团。在LiOH、K 2 CO 3或DBU作为碱的存在下，在室温和空气下实现二取代或三取代的肉桂酸乙酯衍生物的立体选择性制备。通过 ( E )-3-(4-溴苯基)丙烯酸乙酯的合成证明，相同的低共熔混合物（氯化胆碱/尿素）被证明可在连续三次运行中重复使用。可以进行克级反应（10 mmol）而不会形成副产物，从而确保高原子经济性和EcoScale评分为71。
• Synthesis and antiproliferative action of a novel series of maprotiline analogues
  作者：Y.M. McNamara、S.A. Bright、A.J. Byrne、S.M. Cloonan、T. McCabe、D.C. Williams、M.J. Meegan

  DOI：10.1016/j.ejmech.2013.10.076

  日期：2014.1

  The synthesis of a diverse library of compounds structurally related to maprotiline, a norepinephrine reuptake transporter (NET) selective antidepressant which has recently been identified as a novel in vitro antiproliferative agent against Burkitt's lymphoma (BL) cell lines is reported. A series of 9,10-dihydro-9,10-ethanoanthracenes were synthesised with modifications to the bridge of the dihydroethanoanthracene structure and with alterations to the basic side chain. A number of compounds were found to reduce cell viability to a greater extent than maprotiline in BL cell lines. In addition a related series of novel 9-substituted anthracene compounds were investigated as intermediates in the synthesis of 9,10-dihydro-9,10-ethanoanthracenes. These compounds proved the most active from the screen and were found to exert a potent caspase-dependant apoptotic effect in the BL cell lines, while having minimal effect on the viability of peripheral blood mononuclear cells (PBMCs). Compounds also displayed activity in multi-drug resistant (MDR) cells. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Syntheses of selected .epsilon.-(2- or 9-anthryl)alkanoic acids and certain esters - carbon-13 spin-lattice relaxation time measurements of methyl 5-(2-anthryl)pentanoate and methyl 7-(2-anthryl)heptanoate
  作者：Palanisamy Arjunan、Nagaraj Shymasundar、K. Darrell Berlin、Dada Najjar、Mark G. Rockley

  DOI：10.1021/jo00316a029

  日期：1981.1