2-Methyl-3-phenoxy-1,3-butadiene | 137959-97-8

• 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-Methyl-3-phenoxy-1,3-butadiene
• 英文别名: 3-Methylbuta-1,3-dien-2-yloxybenzene
• CAS: 137959-97-8
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: XYGXYVNTNHBVSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  229.6±9.0 °C(Predicted)
• 密度：
  0.946±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Methyl-3-phenoxy-1,3-butadiene 、 丁炔二酸二甲酯 在 对苯二酚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 Dimethyl 5-methyl-4-phenoxyphthalate
  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：

  苯酚 、 alkaline earth salt of/the/ methylsulfuric acid 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， 反应 23.0h， 生成 2-Methyl-3-phenoxy-1,3-butadiene
  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。
• COMPOSITION FOR FORMING FINE RESIST PATTERN AND PATTERN FORMATION METHOD USING SAME
  申请人：AZ ELECTRONIC MATERIALS MANUFACTURING (JAPAN) KK

  公开号：US20150253669A1

  公开（公告）日：2015-09-10

  The present invention provides a fine pattern-forming composition enabling to form a resist pattern having high dry etching resistance, and also provides a pattern formation method using that composition. This formation method hardly causes pipe blockages in the production process. The composition is used for miniaturizing a resist pattern by fattening in a process of forming a negative resist pattern from a chemically amplified resist composition, and comprises a polymer containing a repeating unit having a hydroxyaryl group and an organic solvent not dissolving the negative resist pattern. In the formation method, the fine pattern-forming composition and the resist composition are individually cast with the same coating apparatus, so as to prevent pipe blockages.
• US9360756B2
  申请人：——

  公开号：US9360756B2

  公开（公告）日：2016-06-07