α-Chlor-p-methylbenzyl-methyl-ether | 56377-70-9

• 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: α-Chlor-p-methylbenzyl-methyl-ether
• 英文别名: (α-chloro-4-methyl-benzyl)-methyl ether；(α-Chlor-4-methyl-benzyl)-methyl-aether；1-[Chloro(methoxy)methyl]-4-methylbenzene
• CAS: 56377-70-9
• 化学式: C₉H₁₁ClO
• 分子量: 170.639
• InChiKey: KFQWWEALJZQIMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  α-Chlor-p-methylbenzyl-methyl-ether 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,8-Dihydroxy-10-[(4-methylphenyl)methylen]-9(10H)-anthracenone
  参考文献：
  名称：

  Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase

  摘要：

  The syntheses, the biological evaluation, and the structure-activity relationships of a novel series of 1,8-dihydroxy-9(10H)-anthracenones bearing acyl-, alkyl-, or alkylidene-linked aromatic substituents in the 10-position are described. The phenylacyl and phenylalkylidene analogs were far more potent inhibitors of 5-lipoxygenase (5-LO) from bovine polymorphonuclear leukocytes (IC50 values in the 10(-7) M range) than the antipsoriatic drug anthralin, whereas phenylalkyl analogs were only weak inhibitors. Among the active compounds were both potent generators of hydroxyl radicals, as determined by deoxyribose degradation, and strong reducers of the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). However, several derivatives of this series maintained 5-LO inhibitory activity but did not generate hydroxyl radicals and were not reactive with DPPH. In particular, phenylacyl analogs were also 6 times more efficient in inhibition of lipid peroxidation in model membranes than anthralin. Structure-activity relationships have shown that the presence of free phenolic groups in the attached aromatic ring is beneficial but not required for 5-LO inhibitory potency. The inhibitory potency in the 10-phenylacyl series increased with the length of the acyl chain with three methylene units being the optimum, suggesting a specific enzyme interaction which would not be expected for nonspecific redox inhibitors.

  DOI：

  10.1021/jm00077a015
• 作为产物：
  描述：

  对甲基苯甲醛 在 盐酸 、 甲醇 、 氯化亚砜 作用下， 生成 α-Chlor-p-methylbenzyl-methyl-ether
  参考文献：
  名称：

  Straus; Weber, Justus Liebigs Annalen der Chemie, 1932, vol. 498, p. 101,107

  摘要：

  DOI：

文献信息

• Synthesis of amines
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0008532A1

  公开（公告）日：1980-03-05

  A process for the preparation of an amide of the formula wherein R is an eventually substituted alkyl, alkenyl, aralkyl or phenyl group, by hydrolysis of a nitrile of the formula (II) wherein R is as defined above, in the presence of a base and hydrogen peroxide using an organic quaternary ammonium salt and/or a tertiary amine as a catalyst. This process is useful for the preparation of amides of formula (III) wherein n is 1, 2 or 3 Ar and Ar' are eventually substituted phenyl groups R3 is hydrogen or a substituent. These amides can be decomposed in amines by a halogen or a hypohalite in the presence of a base.

  一种通过水解式（II）腈制备式（I）酰胺的工艺 其中 R 是最终取代的烷基、烯基、芳基或苯基，通过水解式（II）的腈 其中 R 如上定义，在碱和过氧化氢存在下，使用有机季铵盐和/或叔胺作为催化剂。该工艺可用于制备式 (III) 的酰胺 其中 n 为 1、2 或 3 Ar 和 Ar'为最终取代的苯基 R3 是氢或取代基。 这些酰胺可以在碱存在下通过卤素或次卤素分解成胺。
• Mechanism of thermolysis of .alpha.-chloro ethers in aprotic solvents
  作者：H. Kwart、P. A. Silver

  DOI：10.1021/jo00909a004

  日期：1975.10
• Straus; Heinze, Justus Liebigs Annalen der Chemie, 1932, vol. 493, p. 191,207
  作者：Straus、Heinze

  DOI：——

  日期：——
• US4536599A
  申请人：——

  公开号：US4536599A

  公开（公告）日：1985-08-20
• Antipsoriatic anthrones with modulated redox properties. 1. Novel 10-substituted 1,8-dihydroxy-9(10H)-anthracenones as inhibitors of 5-lipoxygenase
  作者：Klaus Mueller、Dieter Guerster、Susanne Piwek、Wolfgang Wiegrebe

  DOI：10.1021/jm00077a015

  日期：1993.12

  The syntheses, the biological evaluation, and the structure-activity relationships of a novel series of 1,8-dihydroxy-9(10H)-anthracenones bearing acyl-, alkyl-, or alkylidene-linked aromatic substituents in the 10-position are described. The phenylacyl and phenylalkylidene analogs were far more potent inhibitors of 5-lipoxygenase (5-LO) from bovine polymorphonuclear leukocytes (IC50 values in the 10(-7) M range) than the antipsoriatic drug anthralin, whereas phenylalkyl analogs were only weak inhibitors. Among the active compounds were both potent generators of hydroxyl radicals, as determined by deoxyribose degradation, and strong reducers of the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). However, several derivatives of this series maintained 5-LO inhibitory activity but did not generate hydroxyl radicals and were not reactive with DPPH. In particular, phenylacyl analogs were also 6 times more efficient in inhibition of lipid peroxidation in model membranes than anthralin. Structure-activity relationships have shown that the presence of free phenolic groups in the attached aromatic ring is beneficial but not required for 5-LO inhibitory potency. The inhibitory potency in the 10-phenylacyl series increased with the length of the acyl chain with three methylene units being the optimum, suggesting a specific enzyme interaction which would not be expected for nonspecific redox inhibitors.