benz[a]anthracen-5-yl-methyl ether | 56183-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: benz[a]anthracen-5-yl-methyl ether
• 英文别名: Benz[a]anthracen-5-yl-methyl-aether；5-Methoxy-benz[a]anthracen；3-Methoxy-1.2-benzo-anthracen；5-Methoxybenz<α>anthracen；5-Methoxi-benz-anthracen；5-Methoxy-benzanthracen；BENZ(a)ANTHRACENE, 5-METHOXY-；5-methoxybenzo[a]anthracene
• CAS: 56183-20-1
• 化学式: C₁₉H₁₄O
• 分子量: 258.32
• InChiKey: WNBLRQQLYZGZRI-UHFFFAOYSA-N

物化性质

• 沸点：
  361.57°C (rough estimate)
• 密度：
  1.0651 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

SDS

反应信息

• 作为反应物：
  描述：

  benz[a]anthracen-5-yl-methyl ether 在 氢溴酸 、 溶剂黄146 作用下， 生成 5-羟基苯并[a]蒽
  参考文献：
  名称：

  Fieser; Dietz, Journal of the American Chemical Society, 1929, vol. 51, p. 3144

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲氧基-12H-苯并[a]蒽-7-酮 在 乙醇 、 aluminium amalgam 、 氨 作用下， 生成 benz[a]anthracen-5-yl-methyl ether
  参考文献：
  名称：

  Fieser; Dietz, Journal of the American Chemical Society, 1929, vol. 51, p. 3144

  摘要：

  DOI：

文献信息

• STUDIES IN THE WAGNER–MEERWEIN REARRANGEMENT: PART IV. DERIVATIVES OF BENZ[b]FLUORENE
  作者：F. A. L. Anet、P. M. G. Bavin

  DOI：10.1139/v60-032

  日期：1960.2.1

  10-Methyl-10-benz[b]fluorenylmethyl tosylate gave mainly 5-methylbenz[a]anthracene on formolysis, but the related alcohol gave a mixture of the 5- and 6-methyl isomers by reaction with phosphorus pentoxide. Reaction of benz[b]fluorenone with excess diazomethane gave 5-methoxybenz[a]anthracene as the only isolable product. The alkylation of methyl benz[b]fluorene-10-carboxylate was studied.

  10-甲基-10-苯并[b]芴基甲基甲苯磺酸酯通过甲解主要得到5-甲基苯并[a]蒽，但相关的醇通过与五氧化二磷反应得到5-和6-甲基异构体的混合物。苯并[b]芴酮与过量的重氮甲烷反应得到5-甲氧基苯并[a]蒽作为唯一的可分离产物。研究了苯并[b]芴-10-羧酸甲酯的烷基化反应。
• 42. Oxidation of carcinogenic hydrocarbons by osmium tetroxide
  作者：J. W. Cook、R. Schoental

  DOI：10.1039/jr9480000170

  日期：——
• Sterically induced methoxyl migration on acid-catalyzed dehydration of K-region trans-dihydrodiol monomethyl ethers
  作者：Nashaat T. Nashed、Tata Venkata S. Rao、Donald M. Jerina

  DOI：10.1021/jo00075a030

  日期：1993.11

  The regioisomers of the trans-dihydrodiol monomethyl ethers (DME) at the K-regions of 4- and 7-methyl- and 7,12-dimethylbenz[a] anthracene, which possess a ring methyl substituent peri to the methoxyl group, react with BF3.etherate to form a single phenol and two regioisomeric phenol methyl ethers, one of which arises by migration of the methoxyl group. In contrast, for DME of benz[a]-anthracene and its 1-, 4-, 7-, 11- and 12-methyl- and 7,12-dimethyl-substituted derivatives where there is no peri methyl group, methoxyl migration does not occur, and thus only the phenol methyl ether resulting from loss of water is formed. These results are consistent with a mechanism in which the initially formed carbocation with a pseudoaxial methoxyl group must undergo either conformational change to align the bond of the leaving proton with the empty p-orbital prior to proton loss or migration of the methoxyl group to the adjacent carbocation via a cyclic oxonium ion. In the absence of a ring substituent peri to the methoxyl group, conformational change is faster than formation of the cyclic oxonium ion, and therefore migration of the methoxyl group does not occur. A methyl substituent peri to the methoxyl group raises the activation energy barrier for conformational isomerization due to adverse steric interaction between the two groups. Consequently, formation of the cyclic oxonium ion becomes competitive with conformational change. The resulting oxonium ion opens to the regioisomeric carbocation resulting in rearrangement. Formation of the cyclic oxonium ion in these reactions is analogous to the rapid internal return of the hydroxy carbocation intermediate to protonated epoxide that is thought to occur in the reactions of peri-methyl-substituted K-region arene oxides.
• WEEKS, STEPHAN;GILLES, STEVEN;DOBSON, ROY;SENNE, SCOTT;DSILVA, ARTHUR P., ANAL. CHEM., 62,(1990) N4, C. 1472-1477
  作者：WEEKS, STEPHAN、GILLES, STEVEN、DOBSON, ROY、SENNE, SCOTT、DSILVA, ARTHUR P.

  DOI：——

  日期：——
• Fieser; Dietz, Journal of the American Chemical Society, 1929, vol. 51, p. 3144
  作者：Fieser、Dietz

  DOI：——

  日期：——