ethyl (E)-3-(4-(methylthio)phenyl)acrylate | 125872-45-9

• 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: ethyl (E)-3-(4-(methylthio)phenyl)acrylate
• 英文别名: ethyl (E)-3-(4-methylsulfanylphenyl)prop-2-enoate
• CAS: 125872-45-9
• 化学式: C₁₂H₁₄O₂S
• 分子量: 222.308
• InChiKey: XJOWBCLMLDMBNG-RMKNXTFCSA-N

物化性质

• 熔点：
  45-46 °C(Solv: ethanol (64-17-5))
• 沸点：
  345.8±25.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-(4-(methylthio)phenyl)acrylate 在 双氧水 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (E)-4-(methylsulfonyl)cinnamic acid
  参考文献：
  名称：

  Central Cholinergic Agents. II. Synthesis and Acetylcholinesterase Inhibitory Activities of N-(.OMEGA.-(N-Alkyl-N-(phenylmethyl)amino)alkyl)-3-arylpropenamides.

  摘要：

  制备了一系列 N-[ω-[N-苯基甲基]氨基]烷基-3-芳基丙烯酰胺，并测试了其对乙酰胆碱酯酶的抑制活性。发现该系列中的一些化合物是强效抑制剂。对其结构-活性关系进行了详细讨论。

  DOI：

  10.1248/cpb.39.3236
• 作为产物：
  描述：

  (E)-3-(4-(methylthio)phenyl)acrylic acid 在 乙醇 、 硫酸 作用下， 生成 ethyl (E)-3-(4-(methylthio)phenyl)acrylate
  参考文献：
  名称：

  Dani; Nargund, Journal of the Karnatak University, 1959, vol. 4, p. 26,28

  摘要：

  DOI：

文献信息

• Synthesis and Antifungal Activities of R-102557 and Related Dioxane-Triazole Derivatives.
  作者：Sadao OIDA、Yawara TAJIMA、Toshiyuki KONOSU、Yoshie NAKAMURA、Atsushi SOMADA、Teruo TANAKA、Shinobu HABUKI、Tamako HARASAKI、Yasuki KAMAI、Takashi FUKUOKA、Satoshi OHYA、Hiroshi YASUDA

  DOI：10.1248/cpb.48.694

  日期：——

  Novel triazole compounds with a dioxane ring were synthesized. Condensation of the diol precursor 10 with various aromatic aldehydes 11-13 under acidic conditions afforded a series of dioxane-triazole compounds 14-16. The antifungal activities of the compounds 14-16 were evaluated in vivo in mice infection models against Candida and Aspergillus species. High activities were seen for the derivatives with one or two double bond(s) and an aromatic ring substituted with an electron-withdrawing group in th side chain. Among the derivatives, R-102557 (16R : Ar=4-(2, 2, 3, 3)-tetrafluoropropoxy)phenyl)showed excellent in vivo activities against Candida, As-pergillus and Cryptococcus species. It also showed high tolerance in a preliminary toxicity study in rats.

  具有二噁烷环的新型三唑化合物被合成。在酸性条件下，二醇前体10与各种芳香醛11-13缩合，得到了一系列二噁烷-三唑化合物14-16。这些化合物14-16的抗真菌活性通过在小鼠感染模型中对白色念珠菌和曲霉菌的评估进行了体内评价。含有单个或两个双键且侧链上带有吸电子基团的芳环衍生物表现出较高的活性。在这些衍生物中，R-102557（16R：Ar=4-（2,2,3,3-四氟丙氧基）苯基）对白色念珠菌、曲霉菌和隐球菌属表现出极佳的体内活性。在大鼠的初步毒性研究中也显示出高度耐受性。
• Hypervalent iodine(<scp>iii</scp>) induced oxidative olefination of benzylamines using Wittig reagents
  作者：Vijayalakshmi Ramavath、Bapurao D. Rupanawar、Satish G. More、Ajay H. Bansode、Gurunath Suryavanshi

  DOI：10.1039/d1nj01170g

  日期：——

  and secondary benzylamines using 2C-Wittig reagents, which provides easy access to α,β-unsaturated esters. Mild reaction conditions, good to excellent yields with high (E) selectivity, and a broad substrate scope are the key features of this reaction. We have successfully carried out the gram-scale synthesis of α,β-unsaturated esters.

  我们使用2C-Wittig试剂开发了高价碘（III）诱导的伯苄胺和仲苄胺的氧化烯化反应，该反应可轻松获得α，β-不饱和酯。温和的反应条件，具有高（E）选择性的良好至优异的产率以及广泛的底物范围是该反应的关键特征。我们已经成功地进行了克级的α，β-不饱和酯的合成。
• Integrating Allyl Electrophiles into Nickel‐Catalyzed Conjunctive Cross‐Coupling
  作者：Van T. Tran、Zi‐Qi Li、Timothy J. Gallagher、Joseph Derosa、Peng Liu、Keary M. Engle

  DOI：10.1002/anie.201915454

  日期：2020.4.27

  offer exciting possibilities in organic synthesis but remains largely unknown. Herein, we report the use of allyl electrophiles in nickel-catalyzed conjunctive cross-coupling with a non-conjugated alkene and dimethylzinc. The transformation is enabled by weakly coordinating, monodentate aza-heterocycle directing groups that are useful building blocks in synthesis, including saccharin, pyridones, pyrazoles

  烯丙基化和联合交叉偶联代表了催化中两种有用但很大程度上不同的反应范式。这两个过程的结合将为有机合成提供令人兴奋的可能性，但仍然很大程度上未知。在此，我们报道了烯丙基亲电子试剂在镍催化的与非共轭烯烃和二甲基锌的连接交叉偶联中的应用。这种转化是通过弱配位的单齿氮杂环导向基团实现的，这些导向基团是合成中有用的结构单元，包括糖精、吡啶酮、吡唑和三唑。该反应在温和条件下发生，并且与多种烯丙基亲电子试剂兼容。起始材料的 β-γ 烯烃的容易反应性证明了通过底物方向性实现的高化学选择性，而产物的 ϵ-ζ 烯烃被保留。通过开发炔烃底物的类似方法，进一步说明了这种方法的普遍性。机理研究揭示了弱配位导向基团解离对于允许烯丙基部分结合并促进 C(sp3 )-C(sp3 ) 还原消除的重要性。
• A two-step ball milling method synthesizes and purifies α,β-unsaturated esters
  作者：William C. Shearouse、Chelsea M. Korte、James Mack

  DOI：10.1039/c0gc00671h

  日期：——

  Over the last decade, solvent-free methods have been gaining interest as replacements for traditional organic chemistry techniques. While solvent-free methods are well known for many processes, a simple, solvent-free purification procedure that supplements them does not exist. We report the solvent-free synthesis of α,β-unsaturated esters using a solvent-free Horner–Wadsworth–Emmons (HWE) reaction using high-speed ball milling (HSBM). We were able to perform the HWE reaction on a variety of aldehydes, and isolate their respective a,b-unsaturated esters in high yields, purities, and diastereoselectivities.

  过去十年来，无溶剂方法作为传统有机化学技术的替代品，越来越受到关注。尽管无溶剂方法在很多过程中广为人知，但补充这些方法的简单无溶剂纯化程序尚未出现。我们报道了通过高转速球磨（HSBM）进行的无溶剂Horner-Wadsworth-Emmons（HWE）反应，实现了α,β-不饱和酯的无溶剂合成。我们成功地在多种醛上进行了HWE反应，并以高产率、纯度和非对映选择性分离出相应的α,β-不饱和酯。
• Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor–Acceptor Cyclopropanes
  作者：Matteo Faltracco、Matteo Damian、Eelco Ruijter

  DOI：10.1021/acs.orglett.1c02795

  日期：2021.10.1

  An alkylation/olefination cascade of indolecarboxaldehydes and phosphonate-functionalized donor–acceptor cyclopropanes affords functionalized dihydrocarbazoles and cyclohepta[cd]indoles in formal (3 + 3) and (4 + 3) cycloadditions. A minor modification to the reaction conditions also allows access to the fully aromatic heterocyclic scaffolds by thermal loss of an electron-rich aryl moiety.

  吲哚甲醛和膦酸酯官能化的供体-受体环丙烷的烷基化/烯化级联以正式的 (3 + 3) 和 (4 + 3) 环加成提供官能化的二氢咔唑和环庚烷 [ cd ] 吲哚。对反应条件的微小修改还允许通过富含电子的芳基部分的热损失获得完全芳香族杂环支架。