(5'-(((tert-butyldimethylsilyl)oxy)methyl)-2',4-bis(methoxymethoxy)-[1,1'-biphenyl]-3-yl)methanol | 711012-15-6

• 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: (5'-(((tert-butyldimethylsilyl)oxy)methyl)-2',4-bis(methoxymethoxy)-[1,1'-biphenyl]-3-yl)methanol
• CAS: 711012-15-6
• 化学式: C₂₄H₃₆O₆Si
• 分子量: 448.632
• InChiKey: BYSXDNKZOFOAPY-UHFFFAOYSA-N

物化性质

• 沸点：
  512.6±50.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (5'-(((tert-butyldimethylsilyl)oxy)methyl)-2',4-bis(methoxymethoxy)-[1,1'-biphenyl]-3-yl)methanol 在 Wilkinson's catalyst 吡啶 、 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 氢氟酸 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 45.0h， 生成 5-allyl-3'-propyl-biphenyl-2,4'-diol
  参考文献：
  名称：

  Efficient synthesis and structure–activity relationship of honokiol, a neurotrophic biphenyl-type neolignan

  摘要：

  Honokiol, a biphenyl-type neolignan, which shows the remarkable neurotrophic effect in primary cultured rat cortical neurons, has been effectively synthesized in 21% yield over 14 steps starting from 5-bromosalicylic acid and p-hydroxybenzoic acid by utilizing Pd-catalyzed Suzuki-Miyaura coupling reaction as a key step. Additionally, the structure-activity relationship between neurite outgrowth-promoting activity and its O-methylated and/or its hydrogenated analogues was examined in the primary cultures of fetal rat cortical neurons, suggesting that 5-allyl and T-hydroxyl groups are essential for affecting the neurotrophic activity of honokiol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.067
• 作为产物：
  描述：

  5'-(tert-Butyl-dimethyl-silanyloxymethyl)-4,2'-bis-methoxymethoxy-biphenyl-3-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到(5'-(((tert-butyldimethylsilyl)oxy)methyl)-2',4-bis(methoxymethoxy)-[1,1'-biphenyl]-3-yl)methanol
  参考文献：
  名称：

  Efficient synthesis and structure–activity relationship of honokiol, a neurotrophic biphenyl-type neolignan

  摘要：

  Honokiol, a biphenyl-type neolignan, which shows the remarkable neurotrophic effect in primary cultured rat cortical neurons, has been effectively synthesized in 21% yield over 14 steps starting from 5-bromosalicylic acid and p-hydroxybenzoic acid by utilizing Pd-catalyzed Suzuki-Miyaura coupling reaction as a key step. Additionally, the structure-activity relationship between neurite outgrowth-promoting activity and its O-methylated and/or its hydrogenated analogues was examined in the primary cultures of fetal rat cortical neurons, suggesting that 5-allyl and T-hydroxyl groups are essential for affecting the neurotrophic activity of honokiol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.067

文献信息

• Bioorg. Med. Chem. Lett. 2004. 14, 2621-2625
  作者：

  DOI：——

  日期：——