1-(4-methoxy-phenyl)-2-methylene-but-3-en-1-ol | 145450-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxy-phenyl)-2-methylene-but-3-en-1-ol
• 英文别名: 2-Methylidene-1-(p-methoxyphenyl)but-3-en-1-ol；1-(4-Methoxyphenyl)-2-methylidenebut-3-en-1-ol
• CAS: 145450-40-4
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: LWNMFZKMHCSGNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丁烯酮 、 1-(4-methoxy-phenyl)-2-methylene-but-3-en-1-ol 以 苯 为溶剂， 反应 48.0h， 生成 1-{3-[Hydroxy-(4-methoxy-phenyl)-methyl]-cyclohex-3-enyl}-ethanone 、 1-{4-[Hydroxy-(4-methoxy-phenyl)-methyl]-cyclohex-3-enyl}-ethanone
  参考文献：
  名称：

  手性2-取代-1,3-二烯的Diels-Alder反应中的非对面选择性。

  摘要：

  从氯丁二烯开始，描述了烷基和芳基（1，3-丁二烯-2-基）甲醇1的改进的合成。这些二烯醇或它们的醚3与各种亲二烯体之间的热Diels-Alder反应产生了对单环“对”加合物的公平至良好的区域和非对映选择性。相反，当在路易斯酸的存在下进行二烯醚3的狄尔斯-阿尔德环加成反应时，观察到总区域选择性和优异的π表面选择性。

  DOI：

  10.1016/s0040-4039(00)60028-x
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 1,4-二溴-2-丁炔 在 indium 作用下， 以 水 为溶剂， 反应 6.0h， 以55%的产率得到1-(4-methoxy-phenyl)-2-methylene-but-3-en-1-ol
  参考文献：
  名称：

  在水性介质中的有机金属反应。铟介导的羰基化合物的1，3-丁二烯-2-基化

  摘要：

  在水介质中，铟介导的1，4-二溴-2-丁炔与羰基化合物的偶合得到1，3-丁二烯-2-基甲醇的良好产率。

  DOI：

  10.1021/ol000239k

文献信息

• Thermal and Catalyzed Diels-Alder Reactions with Chiral 2-Substituted-1,3-dienes: Conformational Models for Diastereofacial Selectivity
  作者：Robert Bloch、Nathalie Chaptal-Gradoz

  DOI：10.1021/jo00094a029

  日期：1994.7

  The thermal or BF3-catalyzed Diels-Alder reactions of chiral 2-substituted-1,3-dienes bearing a hydroxy or a protected hydroxy group at the allylic position with various dienophiles have been studied in order to determine the regio- and stereoselective control elements. Good regio- and facial selectivities were ob;served in thermal reaction of dienes bearing a free hydroxy group. The stereoselectivity was reversed and strongly lowered when the hydroxy soup was protected as an ether. However the regio- as well as the stereoselectivity of the cycloaddition of these diene ethers with alpha,beta-unsaturated aldehydes or ketones are remarkably enhanced by the addition of a Lewis acid since in a few cases a unique isomer was formed. These experimental results have been rationalized and could be explained by conformational preferences of the dienes in the transition state. In particular, the reversal of facial selectivity for dienes having a free hydroxy group has been attributed to a hydrogen bonding interaction between the diene and the dienophile.
• Diastereofacial selectivity in Diels-Alder reactions of chiral 2-substituted-1,3-dienes.
  作者：Robert Bloch、Nathalie Chaptal-Gradoz

  DOI：10.1016/s0040-4039(00)60028-x

  日期：1992.10

  described. Thermal Diels-Alder reactions between these dienols or their ethers 3 and various dienophiles give rise with fair to good regio- and diastereoselectivity to monocyclic “para” adducts. In contrast a total regioselectivity and an excellent π-facial selectivity is observed when the Diels-Alder cycloadditions of the dienic ethers 3 are conducted in the presence of a Lewis acid.

  从氯丁二烯开始，描述了烷基和芳基（1，3-丁二烯-2-基）甲醇1的改进的合成。这些二烯醇或它们的醚3与各种亲二烯体之间的热Diels-Alder反应产生了对单环“对”加合物的公平至良好的区域和非对映选择性。相反，当在路易斯酸的存在下进行二烯醚3的狄尔斯-阿尔德环加成反应时，观察到总区域选择性和优异的π表面选择性。
• Organometallic Reactions in Aqueous Media. Indium-Mediated 1,3-Butadien-2-ylation of Carbonyl Compounds
  作者：Wenshuo Lu、Jihai Ma、Yang、Tak Hang Chan

  DOI：10.1021/ol000239k

  日期：2000.11.1

  Indium-mediated coupling of 1,4-dibromo-2-butyne with carbonyl compounds in aqueous media gave good yields of the 1, 3-butadien-2-ylmethanols.

  在水介质中，铟介导的1，4-二溴-2-丁炔与羰基化合物的偶合得到1，3-丁二烯-2-基甲醇的良好产率。