Phenyl 2-methoxyacrylate | 170123-96-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: Phenyl 2-methoxyacrylate
• 英文别名: Phenyl 2-methoxyprop-2-enoate
• CAS: 170123-96-3
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: HKQKRNMVWNZRDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  Phenyl 2-methoxyacrylate 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 Methyl 3-methoxy-4-phenoxybenzoate
  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
• 作为产物：
  描述：

  2-甲氧基丙-2-烯酸 、 苯酚 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 Phenyl 2-methoxyacrylate
  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

• Process for producing alpha, beta-unsaturated carboxylic acid esters and catalyst for use in such process
  申请人：Nippon Shokubai Co., Ltd.

  公开号：EP1123915A1

  公开（公告）日：2001-08-16

  Economical and efficient processes for producing an α, β-unsaturated carboxylic acid heterocycle-inserted ester and an α,β-unsaturated carboxylic acid polyheteroalkylene ester as well as a catalyst suited for use in economically and efficiently producing an α,β-unsaturated carboxylic acid ester are provided. The invention provides (1) a process for producing an α,β-unsaturated carboxylic acid ester which comprises reacting an α,β-unsaturated carboxylic acid ester with a heterocyclic compound, (2) a process for producing an α,β-unsaturated carboxylic acid ester which comprises reacting an α,β-unsaturated carboxylic acid with a heterocyclic compound in the presence of a polymerization inhibitor and a metal oxide catalyst, and (3) a catalyst for the production of an α,β-unsaturated carboxylic acid ester    comprising a metal oxide.

  本发明提供了经济、高效地生产α，β-不饱和羧酸杂环插入酯和α，β-不饱和羧酸聚异链烷烃酯的工艺，以及适用于经济、高效地生产α，β-不饱和羧酸酯的催化剂。 本发明提供 (1）一种生产α，β-不饱和羧酸酯的工艺，它包括使α，β-不饱和羧酸酯与杂环化合物反应、 (2) α，β-不饱和羧酸酯的生产工艺 其中包括使 α，β-不饱和羧酸与杂环化合物反应 在聚合抑制剂和金属氧化物催化剂存在下，以及 (3) α,β-不饱和羧酸酯生产催化剂 包括一种金属氧化物。
• Process for producing alpha , beta-unsaturated carboxylic acid esters and catalyst for use in such process
  申请人：Nippon Shokubai Company Ltd.

  公开号：US20010034300A1

  公开（公告）日：2001-10-25

  Economical and efficient processes for producing an &agr;, &bgr;-unsaturated carboxylic acid heterocycle-inserted ester and an &agr;,&bgr;-unsaturated carboxylic acid polyheteroalkylene ester as well as a catalyst suited for use in economically and efficiently producing an &agr;,&bgr;-unsaturated carboxylic acid ester are provided. The invention provides (1) a process for producing an &agr;,&bgr;-unsaturated carboxylic acid ester which comprises reacting an &agr;,&bgr;-unsaturated carboxylic acid ester with a heterocyclic compound, (2) a process for producing an &agr;,&bgr;-unsaturated carboxylic acid ester which comprises reacting an &agr;,&bgr;-unsaturated carboxylic acid with a heterocyclic compound in the presence of a polymerization inhibitor and a metal oxide catalyst, and (3) a catalyst for the production of an &agr;,&bgr;-unsaturated carboxylic acid ester comprising a metal oxide.

  本发明提供了经济、高效地生产&agr;,&bgr;-不饱和羧酸杂环插入酯和&agr;,&bgr;-不饱和羧酸聚异烯烃酯的工艺，以及适合用于经济、高效地生产&agr;,&bgr;-不饱和羧酸酯的催化剂。 本发明提供 (1）一种生产&agr;,&bgr;-不饱和羧酸酯的工艺，它包括使&agr;,&bgr;-不饱和羧酸酯与杂环化合物反应、 (2) 一种生产&agr;,&bgr;-不饱和羧酸酯的工艺，其中包括将&agr;,&bgr;-不饱和羧酸酯与杂环化合物反应。 其中包括使不饱和羧酸与杂环化合物反应 在聚合抑制剂和金属氧化物催化剂存在下反应，以及 (3) 用于生产&agr;,&bgr;-不饱和羧酸酯的催化剂 包括一种金属氧化物。
• US6541656B2
  申请人：——

  公开号：US6541656B2

  公开（公告）日：2003-04-01
• 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.