苯甲酸,3-甲基-4-苯氧基-,甲基酯 | 137960-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯甲酸,3-甲基-4-苯氧基-,甲基酯
• 英文名称: methyl 3-methyl-4-phenoxybenzoate
• 英文别名: 3-Methyl-4-phenoxy-benzoic acid methyl ester
• CAS: 137960-08-8
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: CKYDZVKKBMMCTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲酸,3-甲基-4-苯氧基-,甲基酯 在 甲醇 、 水 、 lithium hydroxide 作用下， 以93 %的产率得到3-methyl-4-phenoxybenzoic acid
  参考文献：
  名称：

  [EN] PHARMACEUTICAL COMPOUNDS FOR THE TREATMENT OF COMPLEMENT MEDIATED DISORDERS
  [FR] COMPOSÉS PHARMACEUTIQUES POUR LE TRAITEMENT DE TROUBLES MÉDIÉS PAR LE COMPLÉMENT

  摘要：

  This disclosure provides compounds, compositions, and methods to treat medical disorders, such as complement-mediated disorders, including complement C1s-mediated disorders.

  公开号：

  WO2023183405A2
• 作为产物：
  描述：

  甲基丙烯酸苯酯 在 对苯二酚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 为溶剂， 反应 42.0h， 生成 苯甲酸,3-甲基-4-苯氧基-,甲基酯
  参考文献：
  名称：

  Synthesis of Functionalized Aryloxy 1,3-Butadienes and Their Transformation to Diaryl Ethers via Diels-Alder Cycloaddition Reactions

  摘要：

  The Diels-Alder reaction involving cycloaddition of aryloxy-substituted 1,3-butadienes with appropriate acetylenic electrophiles, followed by aromatization of the newly formed cyclohexadiene ring, has been used for the synthesis of diaryl ethers. The functionalized aryloxy 1,3-butadienes employed in this study were prepared by either of two methods: (1) methylenation of aryl esters via the Tebbe or related reagents, and (2) from 1-(aryloxy)-2-propanone by a sequence of formylation or alkylthio methlylenation, and subsequent enolsilylation. A tetrasubstituted butadiene containing two phenoxy groups at the 1 and 3 positions also was prepared by the latter method. The cycloaddition reactions of 2,3-dioxy-substituted dienes occurred in high yield, but, as expected, with no regioselectivity to furnish nearly equal mixtures of regioisomeric cycloadducts. In contrast, application of 1,2,3-trihetero-substituted dienes resulted in regiospecific cycloaddition reactions. Transformation of the cyclohexadiene cycloadducts to an aromatic ring was accomplished by dehydrogenation with DDQ or by elimination during the cycloaddition process of a molecule of an alkyl mercaptan. A chiral acetylenic ketone derived from D- or L-serine underwent condensation, without racemization, with aryloxy dienes to provide diaryl ethers related to the isodityrosine antibiotics.

  DOI：

  10.1021/jo00124a010

文献信息

• Synthesis of oxazolidine derivatives of β-[3-(aryloxy)aryl]-α-amino acids by application of the diels-alder reaction
  作者：Richard K. Olsen、Xianqi Feng

  DOI：10.1016/s0040-4039(00)93539-1

  日期：1991.10

  The Diels-Alder reaction has been used to construct the diaryl ether unit in oxazolidine derivatives of β-[3-(aryloxy)aryl]-α-amino acids. Cycloaddition of acetylenic ketone 6 with substituted aryloxy dienes, and subsequent aromatization, provided the title compounds in good yields. Reaction of 6 with Danishefsky's diene furnished optically pure derivatives of L-tyrosine.

  Diels-Alder反应已经用于在β-[3-（芳氧基）芳基]-α-氨基酸的恶唑烷衍生物中构建二芳基醚单元。炔基酮6与取代的芳氧基二烯的环加成反应，以及随后的芳构化，以高收率提供了标题化合物。6与Danishefsky's diene的反应提供了光学纯的L-酪氨酸衍生物。
• Copper Single Atoms Chelated on Ligand‐Modified Carbon for Ullmann‐type C−O Coupling
  作者：Vincenzo Ruta、Giovanni Di Liberto、Francesco Moriggi、Yurii P. Ivanov、Giorgio Divitini、Gianlorenzo Bussetti、Vincenzina Barbera、Mark A. Bajada、Maurizio Galimberti、Gianfranco Pacchioni、Gianvito Vilé

  DOI：10.1002/cssc.202301529

  日期：2024.3.8

  Cross‐coupling reactions are of great importance in chemistry due to their ability to facilitate the construction of complex organic molecules. Among these reactions, the Ullmann‐type C−O coupling between phenols and aryl halides is particularly noteworthy and useful for preparing diarylethers. However, this reaction typically relies on homogeneous catalysts that rapidly deactivate under harsh reaction conditions. In this study, we introduce a novel heterogeneous catalyst for the Ullmann‐type C−O coupling reaction, comprised of isolated Cu atoms chelated to a tetraethylenepentamine‐pyrrole ligand that is immobilized on graphite nanoplatelets. The catalytic study reveals the recyclability of the material, and demonstrates the crucial role of the pyrrole linker in stabilizing the Cu sites. The work expands the potential of single‐atom catalyst nanoarchitectures and underscores the significance of ligands in stabilizing metals in cationic forms, providing a novel, tailored catalyst for cross‐coupling chemistries.

  摘要交叉偶联反应能够促进复杂有机分子的构建，因此在化学中具有重要意义。在这些反应中，酚和芳基卤化物之间的乌尔曼型 C-O 偶联反应尤其值得注意，它有助于制备二元醚。然而，这种反应通常依赖于在苛刻反应条件下会迅速失活的均相催化剂。在本研究中，我们介绍了一种用于乌尔曼型 C-O 偶联反应的新型异相催化剂，它由孤立的铜原子与固定在石墨纳米片上的四乙烯五胺-吡咯配体螯合而成。催化研究揭示了该材料的可回收性，并证明了吡咯配体在稳定铜位点方面的关键作用。这项研究拓展了单原子催化剂纳米结构的潜力，强调了配体在稳定阳离子形式金属方面的重要作用，为交叉偶联化学提供了一种新型的定制催化剂。
• US6057322A
  申请人：——

  公开号：US6057322A

  公开（公告）日：2000-05-02
• Synthesis of Functionalized Aryloxy 1,3-Butadienes and Their Transformation to Diaryl Ethers via Diels-Alder Cycloaddition Reactions
  作者：Richard K. Olsen、Xianqi Feng、Magnus Campbell、Rui-lian Shao、Shivanand K. Math

  DOI：10.1021/jo00124a010

  日期：1995.9

  The Diels-Alder reaction involving cycloaddition of aryloxy-substituted 1,3-butadienes with appropriate acetylenic electrophiles, followed by aromatization of the newly formed cyclohexadiene ring, has been used for the synthesis of diaryl ethers. The functionalized aryloxy 1,3-butadienes employed in this study were prepared by either of two methods: (1) methylenation of aryl esters via the Tebbe or related reagents, and (2) from 1-(aryloxy)-2-propanone by a sequence of formylation or alkylthio methlylenation, and subsequent enolsilylation. A tetrasubstituted butadiene containing two phenoxy groups at the 1 and 3 positions also was prepared by the latter method. The cycloaddition reactions of 2,3-dioxy-substituted dienes occurred in high yield, but, as expected, with no regioselectivity to furnish nearly equal mixtures of regioisomeric cycloadducts. In contrast, application of 1,2,3-trihetero-substituted dienes resulted in regiospecific cycloaddition reactions. Transformation of the cyclohexadiene cycloadducts to an aromatic ring was accomplished by dehydrogenation with DDQ or by elimination during the cycloaddition process of a molecule of an alkyl mercaptan. A chiral acetylenic ketone derived from D- or L-serine underwent condensation, without racemization, with aryloxy dienes to provide diaryl ethers related to the isodityrosine antibiotics.
• [EN] PHARMACEUTICAL COMPOUNDS FOR THE TREATMENT OF COMPLEMENT MEDIATED DISORDERS<br/>[FR] COMPOSÉS PHARMACEUTIQUES POUR LE TRAITEMENT DE TROUBLES MÉDIÉS PAR LE COMPLÉMENT
  申请人：[en]ALEXION PHARMACEUTICALS, INC.

  公开号：WO2023183405A2

  公开（公告）日：2023-09-28

  This disclosure provides compounds, compositions, and methods to treat medical disorders, such as complement-mediated disorders, including complement C1s-mediated disorders.