α-methyl-4-benzyloxy-3-methoxybenzyl alcohol | 74613-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: α-methyl-4-benzyloxy-3-methoxybenzyl alcohol
• 英文别名: 1-(4-(benzyloxy)-3-methoxyphenyl)ethanol；1-(3-Methoxy-4-phenylmethoxyphenyl)ethanol
• CAS: 74613-55-1
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: RRSBSGOQENSWPE-UHFFFAOYSA-N

物化性质

• 熔点：
  47-50 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  400.6±45.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-methyl-4-benzyloxy-3-methoxybenzyl alcohol 在 氧气 、 copper(l) chloride 、 palladium dichloride 作用下， 以 二甲基亚砜 为溶剂， 120.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 以83%的产率得到4-苄氧基-3-甲氧基苯甲醛
  参考文献：
  名称：

  通过连续的C–C键裂解 将羟基化合物逐步降解为醛†

  摘要：

  通过使用不带任何配体和添加剂的双金属催化体系（PdCl 2 + CuCl），通过C-C键的连续裂解将羟基化合物逐步降解为醛。广泛的适用性扩展到芳族，脂肪族，伯和仲醇以及木质素模型化合物的各种范围。

  DOI：

  10.1039/c8cc09504c
• 作为产物：
  描述：

  香草乙酮 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 α-methyl-4-benzyloxy-3-methoxybenzyl alcohol
  参考文献：
  名称：

  使用南极假丝酵母的脂肪酶A和B从乙酰香草醛中获得新的手性结构单元

  摘要：

  乙酰香草醛已经用作合成一系列仲醇的起始原料，这些仲醇通过脂肪酶催化的酯化反应而分解。使用南极假丝酵母的固定化脂肪酶B （Novozym 435，CAL-B）有效分离了1-（4-苄氧基-3-甲氧基苯基）乙醇，而南极假单胞菌的固定化脂肪酶A （Novozym 735，CAL-A）有效地分离了脂肪酶。拆分相应的2-溴和2-氯衍生物的方法。富含对映体的醇是可能用于生物活性化合物合成的新组成部分。

  DOI：

  10.1016/j.tetasy.2006.04.030

文献信息

• Structure–activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities
  作者：Surrinder Koul、Jawahir L. Koul、Subhash C. Taneja、Kanaya L. Dhar、Deshvir S. Jamwal、Kuldeep Singh、Rashmeet K. Reen、Jaswant Singh

  DOI：10.1016/s0968-0896(99)00273-4

  日期：2000.1

  Inhibitors of drug metabolism have important implications in pharmaco-toxicology and agriculture. We have reported earlier that piperine, a major alkaloid of black and long peppers inhibits both constitutive and inducible cytochrome P450 (CYP)dependent drug metabolising enzymes. In the present study, an attempt has been made to prepare several novel synthetic analogues so as to relate various modifications in the parent molecule to the inhibition of CYP activities. Two types of mono-oxygenase reactions arylhydrocarbon hydroxylase (AHH) and 7-methoxycoumarin-O-demethylase (MOCD) have been studied. Inhibition studies were investigated in rat microsomal fraction prepared from untreated, 3MC- and PB- treated rat liver in vitro. Modifications were introduced into the piperine molecule: (i) in the phenyl nucleus, (ii) in the side chain and (iii) in the basic moiety. Thus, 38 compounds have been subjected to such studies, and simultaneously an attempt has also been made to arrive at the structure-activity relationship of synthetic analogues. In general, most of the inhibitory potential of the parent molecule is lost with modification in either of the three components of piperine. Saturation of the side chain resulted in significantly enhanced inhibition of CYP while modifications in the phenyl and basic moieties in few analogues offered maximal selectivity in inhibiting either constitutive or inducible CYP activities. Thus Few novel analogues as CYP inactivators have been synthesized which may have important consequences in pharmacokinetics and bioavailability of drugs. (C) 2000 Elsevier Science Ltd. All rights reserved.