methyl 2-((3-fluorophenyl)(hydroxy)methyl)acrylate | 784144-71-4

• 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: methyl 2-((3-fluorophenyl)(hydroxy)methyl)acrylate
• 英文别名: methyl 2-[(3-fluorophenyl)-hydroxymethyl]prop-2-enoate
• CAS: 784144-71-4
• 化学式: C₁₁H₁₁FO₃
• 分子量: 210.205
• InChiKey: YEFGKPYDCAJMPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-((3-fluorophenyl)(hydroxy)methyl)acrylate 在 氢溴酸 、 溶剂黄146 作用下， 反应 1.0h， 以94%的产率得到(Z)-methyl 2-(bromomethyl)-3-(3-fluorophenyl)acrylate
  参考文献：
  名称：

  Syntheses of β- and γ-fluorophenyl cis- and trans-α-methylene-γ-butyrolactones

  摘要：

  Preparation of a series of cis-gamma-fluorophenyl-beta-phenyl-alpha-methylene-gamma-butyrolactones is reported via 'allylboration' of fluorobenzaldehydes with (E)-methyl 3-phenyl-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)acrylate. The corresponding trans-gamma-fluorophenyl lactones were prepared either (i) via 'allylboration' using the (Z)-reagents or (ii) via an indium triflate-mediated isomerization of the cis-products. The difficulty in isomerizing difluorinated cis-products confirms the probable intermediacy of carbocations. Finally, the synthesis of cis-beta-fluorophenyl-gamma-phenyl-alpha-methylene-gamma-butyrolactones was achieved via an indium-catalyzed allylation-lactonization of aldehydes with (Z)-2-(bromomethyl)-3-(fluorophenyl)acrylates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.07.106
• 作为产物：
  描述：

  丙烯酸甲酯（MA） 、 3-氟苯甲醛 在 三乙烯二胺 作用下， 生成 methyl 2-((3-fluorophenyl)(hydroxy)methyl)acrylate
  参考文献：
  名称：

  α-亚烷基β-内酰胺和环丁酮的Ir催化不对称加氢

  摘要：

  许多天然和药物产品中都存在手性β-内酰胺和环丁酮。手性四元环化合物的立体选择性结构是化学界面临的挑战。本文中，我们报告了通过Ir / In-BiphPHOX催化的不对称加氢对四元环（微型）β-内酰胺和环丁酮进行高度立体控制的结构，从而提供了相应的旋光四元环羰基产物，这些产物带有α-手性碳中心，在温和的反应条件下（1.0-2.5 bar H 2）具有出色的收率（高达99％）和对映选择性（高达98％）持续1.0-10小时）。该反应代表了广泛的底物范围。还进行了催化产物的多种转化，以显示该方案的潜在效用。

  DOI：

  10.1002/cjoc.201800088

文献信息

• Stereoselective synthesis of substituted 1,2-annulated sugars by domino double-Michael addition reaction
  作者：Kadigachalam Parasuraman、Ande Chennaiah、Sateesh Dubbu、A.K. Ibrahim Sheriff、Yashwant D. Vankar

  DOI：10.1016/j.carres.2019.03.007

  日期：2019.5

  A simple, highly stereoselective one-pot methodology for the synthesis of novel 1,2-annulated sugars comprising of oxa-oxa and oxa-carbasugar fused skeletons from 2-nitrogalactal and a sugar-derived enone, obtained from 2-formylgalactal, promoted by KOtBu and CH3ONa respectively is described. Both processes rely on a domino double-Michael addition reaction resulting in the formation of three stereocenters

  一种简单，高度立体选择性的一锅法，用于合成新型1，2-环状糖，该糖由2-硝基半乳糖和由2-甲酰基半乳糖制得的糖衍生的烯酮组成，包括oxa-oxa和oxa-carbasugar融合的骨架。分别描述了KOtBu和CH3ONa。两种方法都依赖于多米诺骨牌双迈克尔加成反应，从而在一个锅中形成了三个立体中心，包括一个四元中心。
• A General Approach to the Synthesis of β2-Amino Acid Derivatives via Highly Efficient Catalytic Asymmetric Hydrogenation of α-Aminomethylacrylates
  作者：Yujuan Guo、Guang Shao、Lanning Li、Wenhao Wu、Ruihong Li、Jingjing Li、Jian Song、Liqin Qiu、Mahavir Prashad、Fuk Yee Kwong

  DOI：10.1002/adsc.201000122

  日期：——

  for the synthesis of a valuable class of α‐aminomethylacrylates via the Baylis–Hillman reaction of different aldehydes with methyl acrylate followed by acetylation of the resulting allylic alcohols and SN2′‐type amination of the allylic acetates. Asymmetric hydrogenation of these diverse olefinic precursors using rhodium(Et‐Duphos) catalysts provided the corresponding β2‐amino acid derivatives with excellent

  通过一种新的策略，通过不同醛类的Baylis-Hillman反应与丙烯酸甲酯的合成，然后合成的烯丙醇的乙酰化和乙酸烯丙酯的S N 2'型胺化反应，合成了有价值的α-氨基甲基丙烯酸酯类。使用铑这些不同的烯属前体的不对称氢化（ET-DUPHOS）催化剂提供了相应的β 2个具有优异的对映选择性的α-氨基酸衍生物和非常高的反应性（高达> 99.5％ee值和S / C = 10,000）。的（第一加氢Ž） -构型底物，研究了β的合成2氨基酸衍生物。对于该反应，还公开了底物几何形状和位阻对反应性和对映选择性的高影响。这个协议提供了用于光学纯β制备高度实用的，容易的和可扩展的方法2 -氨基酸和它们的衍生物在温和的反应条件下进行。
• Diastereodivergent Synthesis of Pyrazoline Derivatives through [3 + 2] Cycloaddition of Baylis–Hillman Adducts and Nitrilimines
  作者：Yuan Zeng、Leijie Zhou、Xing Gao、Yang Wu、Qijun Wang、Zhenyan Guo、Jiaxing Huang、Hongchao Guo

  DOI：10.1002/jhet.3344

  日期：2018.12

  In this paper, a [3 + 2] cycloaddition of Baylis–Hillman adducts and nitrilimines has been achieved under mild reaction conditions, providing a concise approach to access biologically important pyrazoline derivatives.

  在本文中，已经在温和的反应条件下实现了[3 + 2]的Baylis-Hillman加合物和亚硝胺的环加成反应，为获得重要的生物吡唑啉衍生物提供了一种简便的方法。
• Phosphine-Catalyzed [3 + 2] Annulation of Morita–Baylis–Hillman Carbonates with Isoxazole-Based Alkenes
  作者：Jianning Liao、Jipan Dong、Jiaqing Xu、Wei Wang、Yongjun Wu、Yuxia Hou、Hongchao Guo

  DOI：10.1021/acs.joc.0c01948

  日期：2021.2.5

  A phosphine-catalyzed [3 + 2] annulation of Morita–Baylis–Hillman (MBH) carbonates with 3-methyl-4-nitro-5-styrylisoxazoles has been developed to afford various multifunctional isoxazoles in moderate to good yields with moderate to excellent diastereoselectivities. With a spirocyclic chiral phosphine as the catalyst, up to 89% ee was obtained.

  已开发出一种膦催化的森田-贝利斯-希尔曼（MBH）碳酸酯与3-甲基-4-硝基-5-苯乙烯基恶唑的碳酸盐环化反应[3 + 2]，以中等至良好的产率提供各种多功能异恶唑，具有中等至优异的非对映选择性。用螺环手性膦作为催化剂，获得高达89％的ee。
• Visible-Light-Induced Trifluoromethylation of Allylic Alcohols
  作者：Bowen Li、Wubing Zeng、Lin Wang、Zhishuai Geng、Teck-Peng Loh、Peizhong Xie

  DOI：10.1021/acs.orglett.1c01767

  日期：2021.7.2

  organic photoredox-catalyzed dehydroxylative trifluoromethylation of allylic alcohols was developed in an environmentally benign manner. In this reaction, the readily available CF3SO2Na was selected as the trifluoromethylation reagent. The in situ generated byproduct SO2 was reutilized to activate C–OH bond, which enabled this dehydroxylative trifluoromethylation to be performed conveniently. A variety

  以环境友好的方式开发了有机光氧化还原催化的烯丙醇脱羟基三氟甲基化。本反应选用易得的CF 3 SO 2 Na作为三氟甲基化试剂。在原位通过产品生成SO 2被再利用来激活C-OH键，这使此dehydroxylative三氟甲基化将被方便地进行。以高产率和优异的立体选择性获得了多种多功能化的 CF 3 -烯丙基化合物。