2-(((tert-butyldiphenylsilyl)oxy)methyl)acrylic acid | 574741-55-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-(((tert-butyldiphenylsilyl)oxy)methyl)acrylic acid
• 英文别名: 2-[[Tert-butyl(diphenyl)silyl]oxymethyl]prop-2-enoic acid
• CAS: 574741-55-2
• 化学式: C₂₀H₂₄O₃Si
• 分子量: 340.494
• InChiKey: KBPLVIBGVRKWLG-UHFFFAOYSA-N

物化性质

• 沸点：
  434.8±45.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(((tert-butyldiphenylsilyl)oxy)methyl)acrylic acid 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Synthesis of Denosomin–Vitamin D₃ Hybrids and Evaluation of Their Anti-Alzheimer’s Disease Activities

  摘要：

  As an extension of previously conducted studies on developing an anti-Alzheimer's disease agent, denosomin (1-deoxy-24-norsominone, an artificial inducer of neurite elongation), derivatives were designed and synthesized based on the hypothesis that our denosomin would exhibit axonal extension activity via a 1,25D(3)-membrane-associated, rapid response steroid-binding protein (1,25D(3)-MARRS) pathway. The biological assay revealed that the hybridization of characteristic delta-lactone in denosomin and the triene moiety in VD3 was effective to enhance the nerve re-extension activity in amyloid beta (A beta)-damaged neurons.

  DOI：

  10.1021/acs.orglett.5b03138
• 作为产物：
  描述：

  ethyl 2-(tert-butyldiphenylsilyloxymethyl)-acrylate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以84%的产率得到2-(((tert-butyldiphenylsilyl)oxy)methyl)acrylic acid
  参考文献：
  名称：

  Synthesis of Denosomin–Vitamin D₃ Hybrids and Evaluation of Their Anti-Alzheimer’s Disease Activities

  摘要：

  As an extension of previously conducted studies on developing an anti-Alzheimer's disease agent, denosomin (1-deoxy-24-norsominone, an artificial inducer of neurite elongation), derivatives were designed and synthesized based on the hypothesis that our denosomin would exhibit axonal extension activity via a 1,25D(3)-membrane-associated, rapid response steroid-binding protein (1,25D(3)-MARRS) pathway. The biological assay revealed that the hybridization of characteristic delta-lactone in denosomin and the triene moiety in VD3 was effective to enhance the nerve re-extension activity in amyloid beta (A beta)-damaged neurons.

  DOI：

  10.1021/acs.orglett.5b03138

文献信息

• Electrochemistry-Enabled Ir-Catalyzed Vinylic C–H Functionalization
  作者：Qi-Liang Yang、Yi-Kang Xing、Xiang-Yang Wang、Hong-Xing Ma、Xin-Jun Weng、Xiang Yang、Hai-Ming Guo、Tian-Sheng Mei

  DOI：10.1021/jacs.9b11915

  日期：2019.12.4

  Synergistic use of electrochemistry and organometallic catalysis has emerged as a powerful tool for site-selective C-H functionalization, yet this type of transformation has thus far mainly been limited to arene C-H functionaliza-tion. Herein, we report the development of electrochemi-cal vinylic C-H functionalization of acrylic acids with al-kynes. In this reaction an iridium catalyst enables C-H/O-H

  电化学和有机金属催化的协同使用已成为位点选择性 CH 功能化的有力工具，但迄今为止这种类型的转化主要限于芳烃 CH 功能化。在此，我们报告了用炔烃对丙烯酸进行电化学乙烯基 CH 官能化的发展。在该反应中，铱催化剂能够实现 CH/OH 官能化以进行炔环化，从而在未分割的电池中提供具有良好至优异产率的 α-吡喃酮。初步机理研究表明，阳极氧化对于从二烯-Ir(I) 络合物中释放产物和再生 Ir(III) 中间体至关重要，二烯-Ir(I) 络合物是一种配位饱和的 18 电子络合物。重要的，
• Ruthenium- and rhodium-catalyzed cross-coupling reaction of acrylamides with alkenes: efficient access to (Z,E)-dienamides
  作者：Jian Zhang、Teck-Peng Loh

  DOI：10.1039/c2cc36137j

  日期：——

  Ruthenium- and rhodium-catalyzed direct oxidative cross-coupling reactions of acrylamides with alkenes were developed. These methods provide an efficient route for the synthesis of (Z,E)-dienamides in excellent yields with good stereoselectivity. The catalytic systems allowed oxidative olefination of a wide range of alkenes bearing different functional groups, such as CO(2)R, COMe, SO(2)Ph, aryl, CONHBn,

  开发了钌和铑催化的丙烯酰胺与烯烃的直接氧化交叉偶联反应。这些方法提供了以优异的产率和良好的立体选择性合成（Z，E）-二酰胺的有效途径。催化系统可以使各种带有不同官能团的烯烃进行氧化烯化，例如CO（2）R，COMe，SO（2）Ph，芳基，CONHBn，CN，PO（OEt）（2） Weinreb酰胺。
• [EN] COMPOSITIONS AND METHODS FOR PROTEIN LABELING, MODIFICATION, ANALYSIS, AND TARGETED DELIVERY<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LE MARQUAGE, LA MODIFICATION, L'ANALYSE ET LA DÉLIVRANCE CIBLÉE DE PROTÉINES
  申请人：UNIV MASSACHUSETTS

  公开号：WO2020006340A1

  公开（公告）日：2020-01-02

  The invention relates to chemically reactive and/or biologically active compounds, reagents and compositions thereof. More particularly, the invention provides novel reagents that are useful in chemical synthesis, functionalization, delivery, probing and/or analytical measurements of small molecule drugs, proteins, antibodies and other biomolecules. The invention provides novel biologically active agents useful as diagnostics or therapeutics, and related composition and methods of uses thereof.

  该发明涉及化学反应性和/或生物活性化合物、试剂及其组合物。更具体地，该发明提供了在化学合成、功能化、传递、探测和/或小分子药物、蛋白质、抗体和其他生物分子的分析测量中有用的新型试剂。该发明提供了作为诊断或治疗用途的新型生物活性剂，以及相关的组合物和使用方法。
• Parallel Kinetic Resolution of Intramolecular Furan Diels-Alder Cycloadducts via Asymmetric Hydroboration
  作者：Tamara Fulgheri、Philip Cornwall、Andrew R. Turner、Joseph B. Sweeney、Duncan M. Gill

  DOI：10.1002/ejoc.201901407

  日期：2019.11.24

  Simple, parallel and dynamic: asymmetric hydroboration reactions of racemic intramolecular Diels‐Alder furan (IMDAF) cycloadducts give regiodivergent outcomes in which simple, parallel and dynamic kinetic resolutions of the substrate enantiomers may be observed. We report parallel kinetic resolution of intramolecular Diels‐Alder cycloadducts, where up to five stereocentres are defined using asymmetric

  简单、平行和动态：外消旋分子内狄尔斯-阿尔德呋喃 (IMDAF) 环加合物的不对称硼氢化反应产生区域发散结果，其中可以观察到底物对映体的简单、平行和动态动力学拆分。我们报告了分子内 Diels-Alder 环加合物的平行动力学拆分，其中使用不对称硼氢化作为对映体区分反应定义了多达五个立体中心，并揭示了基于可逆环加成的动态动力学拆分的证据。
• Cyclization Cascades via<i>N</i>-Amidyl Radicals toward Highly Functionalized Heterocyclic Scaffolds
  作者：Noelia Fuentes、Wangqing Kong、Luis Fernández-Sánchez、Estíbaliz Merino、Cristina Nevado

  DOI：10.1021/ja5115858

  日期：2015.1.21

  one-pot synthesis of 3,3-disubstituted-2-dihydropyridinones from N-(arylsulfonyl)acrylamides and 1,3-dicarbonyl compounds. In this case, a silver-catalyzed radical cascade process involving the sequential formation of two new C-C bonds and one C-N bond, a formal 1,4-aryl migration, and desulfonylation of the starting material explains the regioselective formation of densely functionalized heterocycles

  在 N-（芳基磺酰基）丙烯酰胺的双键上添加各种自由基可以通过酰胺基自由基中间体 2 触发环化/芳基迁移/脱磺酰化级联反应。在此，我们展示了这些中间体在随后的 CC 和 CX 键中的合成效用 -形成事件以快速建立分子复杂性。首先，我们描述了一种区域选择性一锅法合成 CF3-、SCF3-、Ph2(O)P- 和 N3-indolo[2,1-a]isoquinolin-6(5H)-ones 从 N-[(2 -乙炔基）芳基磺酰基]丙烯酰胺通过多步自由基反应级联。该过程包括一锅法形成四个新键（一个 CX、两个 CC 和一个 CN）、正式的 1,4-芳基迁移和起始材料的脱磺酰化。其次，我们提出了从 N-（芳基磺酰基）丙烯酰胺和 1，3-二羰基化合物。在这种情况下，银催化的自由基级联过程包括连续形成两个新的 CC 键和一个 CN 键、正式的 1,4-芳基迁移和起始材料的脱磺酰化，解释了在直截了当的方式。对