2-[Acetoxy-(4-trifluoromethyl-phenyl)-methyl]-acrylic acid methyl ester | 503073-41-4

• 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: 2-[Acetoxy-(4-trifluoromethyl-phenyl)-methyl]-acrylic acid methyl ester
• 英文别名: Methyl 2-[acetyloxy-[4-(trifluoromethyl)phenyl]methyl]prop-2-enoate
• CAS: 503073-41-4
• 化学式: C₁₄H₁₃F₃O₄
• 分子量: 302.25
• InChiKey: STPPVGZKMVWZKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  359.1±42.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[Acetoxy-(4-trifluoromethyl-phenyl)-methyl]-acrylic acid methyl ester 在 sodium perborate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  壳聚糖/聚乙烯醇稳定铜膜材料在水相中 α, β-不饱和酮、Morita-Baylis-Hillman 醇和酯硼化反应中的应用

  摘要：

  壳聚糖/聚（乙烯醇）稳定的铜纳米颗粒（CP@Cu NPs）被用作非均相催化剂，在温和条件下用于α，β-不饱和酮、MBH 醇和MBH 酯的硼基化。该催化剂不仅在合成有机硼化合物方面表现出显着的效率，而且即使在催化剂的七次循环使用后仍然保持优异的反应活性和稳定性。该方法提供了一种通过有效构建碳硼键来合成有机硼化合物的温和有效的方法。

  DOI：

  10.3390/molecules28145609
• 作为产物：
  描述：

  对三氟甲基苯甲醛 在 吡啶 、 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-[Acetoxy-(4-trifluoromethyl-phenyl)-methyl]-acrylic acid methyl ester
  参考文献：
  名称：

  The Baylis–Hillman chemistry in aqueous media: elucidation of mechanism for synthesis of ether side-product leads to an efficient approach to C–O bond formation

  摘要：

  The formation of an ether from the Baylis-Hillman (BH) adduct during the BH reaction of 5-isoxazolecarboxaldehydes is a common phenomenon if the reaction is allowed to proceed for longer periods. The amount of formation of such ethers depends on the acrylates used and is most significant for tert-butyl acrylates. A study of the plausible mechanism for the formation of these side-products led to reactions of acetates of BH adducts with phenol in aqueous media to yield the corresponding 3-phenoxy alk-2-enoates in good yields. The successful translation of solution phase methodology to solid phase for application towards combinatorial chemistry is discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01561-2

文献信息

• Antileishmanial assessment of isoxazole derivatives against <i>L. donovani</i>
  作者：Sushobhan Mukhopadhyay、Dinesh S. Barak、R. Karthik、Sarvesh K. Verma、Rabi S. Bhatta、Neena Goyal、Sanjay Batra

  DOI：10.1039/d0md00083c

  日期：——

  The antileishmanial activity of a variety of 3-nitro and 3-amino-isoxazoles against promastigote and amastigote stages of L. donovani is described.

  描述了多种3-硝基和3-氨基异噁唑对唐氏利什曼原虫旋毛虫和无毛虫阶段的抗利什曼活性。
• Enantioselective Allylic Substitution of Morita-Baylis-Hillman Adducts Catalyzed by Chiral Bifunctional Ferrocenylphosphines
  作者：Linglong Zhu、Haiwen Hu、Liang Qi、Yi Zheng、Weihui Zhong

  DOI：10.1002/ejoc.201600045

  日期：2016.4

  A series of air-stable chiral ferrocenylphosphines (LB1–LB4) were prepared and used in the asymmetric allylic substitution of Morita–Baylis–Hillman (MBH) adducts with phthalimide under mild reaction conditions; the (R,SFc)-ferrocenylphosphine LB4 afforded the desired amination products 3 in moderate yields with excellent enantioselectivities. The absolute configuration of 3o was confirmed by X-ray

  制备了一系列空气稳定的手性二茂铁基膦 (LB1-LB4)，并在温和的反应条件下用于 Morita-Baylis-Hillman (MBH) 加合物与邻苯二甲酰亚胺的不对称烯丙基取代；(R,SFc)-二茂铁基膦 LB4 以中等产率和优异的对映选择性提供了所需的胺化产物 3。X 射线分析证实了 3o 的绝对构型。
• Reactions of Morita-Baylis-Hillman Acetates with Huisgen Zwitterions: A Novel Strategy for the Synthesis of β-Amino Acid Derivatives
  作者：Vijay Nair、Anu Jose、Rony Paul、Resmi Mohan、Smitha Mathew、A. Biju、Eringathodi Suresh

  DOI：10.1055/s-0028-1088063

  日期：2009.6

  The reaction of Huisgen Zwitterion with Morita-Baylis-Hillman acetates afforded β-amino acid derivatives. Huisgen zwitterion - Morita-Baylis-Hillman acetate - β-amino acid

  Huisgen两性离子与Morita-Baylis-Hillman乙酸酯的反应提供了β-氨基酸衍生物。 Huisgen两性离子-Morita-Baylis-Hillman乙酸酯-β-氨基酸
• The coupling reaction of α-silylamines with Baylis-Hillman adducts by visible light photoredox catalysis
  作者：He Zhao、Niannian Ni、Xiaonian Li、Dongping Cheng、Xiaoliang Xu

  DOI：10.1016/j.tetlet.2020.152746

  日期：2021.2

  The preparation of N-containing α,β-unsaturated carboxylate derivatives from α-silylamine and Baylis-Hillman adducts under visible light irradiation was reported. The formation of α-aminoalkyl radical is regioselective compared with the previous reports. The reaction was successfully performed without additional additives under mild conditions.

  报道了在可见光照射下由α-甲硅烷基胺和Baylis-Hillman加合物制备含N的α，β-不饱和羧酸酯衍生物。与先前的报道相比，α-氨基烷基的形成具有区域选择性。在温和条件下，无需添加其他添加剂即可成功进行反应。
• Synthesis of 3,4,5-Trisubstituted Isoxazoles from Morita-Baylis-Hillman Acetates by an NaNO₂/I₂-Mediated Domino Reaction
  作者：Shashikant U. Dighe、Sushobhan Mukhopadhyay、Shivalinga Kolle、Sanjeev Kanojiya、Sanjay Batra

  DOI：10.1002/anie.201504529

  日期：2015.9.7

  3‐nitro‐5‐(aryl/alkyl)isoxazole‐4‐carboxylates is described. In a cascade event, initial Michael addition of NaNO2 to the MBH acetate furnishes the allylnitro intermediate which undergoes I2‐catalyzed oxidative α‐CH nitration of the nitromethyl subunit followed by [3+2] cycloaddition to afford the title compounds. Structural elaborations of these highly substituted isoxazoles by SNAr reactions and

  本文描述了一种有效的NaNO 2 / I 2介导的Morita-Baylis-Hillman（MBH）乙酸盐单酯转化为3-硝基--5-（芳基/烷基）异恶唑-4-羧酸烷基酯的方法。在一个级联事件，初始迈克尔加成纳米2到MBH醋酸配料其经历我的allylnitro中间2催化的氧化α-C 的硝基甲基亚基h的硝化，接着[3 + 2]环加成，得到标题化合物。这些高度取代的异恶唑通过S N Ar反应和氢解进行结构精制可以得到有用的产品。