(1-methoxypenta-3,4-dien-1-yl)benzene | 72014-28-9

• 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: (1-methoxypenta-3,4-dien-1-yl)benzene
• CAS: 72014-28-9
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: JEYMEZVXVVZWIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-bromo-buta-1,2-diene 、 (1-methoxypenta-3,4-dien-1-yl)benzene 生成 1-Methoxy-4-methyl-1,2-dihydronaphthalene
  参考文献：
  名称：

  PORNET J.; RANDRIANOELINA B.; MIGINIAC L., J. ORGANOMETAL. CHEM., 1979, 174, NO 1, 15-26

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 2-Methyl-butadien-(2.3)-yl-magnesium-bromid 生成 (1-methoxypenta-3,4-dien-1-yl)benzene
  参考文献：
  名称：

  Organometalliques (M = Mg, Zn, Al) derivant de bromures α-alleniques

  摘要：

  DOI：

  10.1016/s0022-328x(00)96158-8

文献信息

• Aryl-Substituted Cyclopropyl Acetylenes as Sensitive Mechanistic Probes in the Gold-Catalyzed Hydration of Alkynes. Comparison to the Ag(I)-, Hg(II)-, and Fe(III)-Catalyzed Processes
  作者：Georgia Velegraki、Manolis Stratakis

  DOI：10.1021/jo401325t

  日期：2013.9.6

  of vinyl carbocations, provides exclusively the corresponding cyclopropyl methyl ketones. On the other hand, in the Ag(I)- or Fe(III)-catalyzed hydration, a profound vinyl carbocationic character appears in the initially formed metal–alkyne complexes, as judged by the partial (Ag+) or exclusive (Fe3+) formation of allene-type rearrangement products. These findings provide clear evidence for subtle electronic

  用金催化的2-苯基或2,2-二苯基环丙基乙炔的水合作用，以敏感的探针追踪乙烯基碳正离子的形成，仅提供相应的环丙基甲基酮。另一方面，在Ag（I）或Fe（III）催化的水合作用中，最初形成的金属-炔烃络合物中会出现深刻的乙烯基碳阳离子特征，这可由部分（Ag +）或排他的（Fe 3 +）形成异戊二烯型重排产物。这些发现为金属-炔配合物（包括Au（I或III），Ag（I），Fe（III）和Hg（II））中的细微电子差异提供了清晰的证据。
• 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.