3-<4-<(tert-Butyldimethylsilyl)oxy>-2,3,5-trimethylphenoxy>propyl bromide | 112109-68-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-<4-<(tert-Butyldimethylsilyl)oxy>-2,3,5-trimethylphenoxy>propyl bromide
• 英文别名: 3-[4-[(tert-butyldimethylsilyl)oxy]-2,3,5-trimethylphenoxy]propyl bromide；3-{4-[(tert-Butyldimethylsilyl)oxy]-2,3,5-trimethylphenoxy}propyl bromide；[4-(3-Bromopropoxy)-2,3,6-trimethylphenoxy]-tert-butyl-dimethylsilane
• CAS: 112109-68-9
• 化学式: C₁₈H₃₁BrO₂Si
• 分子量: 387.432
• InChiKey: AHLOEAAMELFCOX-UHFFFAOYSA-N

物化性质

• 沸点：
  423.8±45.0 °C(predicted)
• 密度：
  1.104±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-<4-<(tert-Butyldimethylsilyl)oxy>-2,3,5-trimethylphenoxy>propyl bromide 在 正丁基锂 、 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.75h， 生成 5-(4-Hydroxy-2,3,5-trimethylphenoxy)-2,2-dimethylpentanoic acid
  参考文献：
  名称：

  Studies on hindered phenols and analogs. 1. Hypolipidemic and hypoglycemic agents with ability to inhibit lipid peroxidation

  摘要：

  A series of hindered phenols were investigated as hypolipidemic and/or hypoglycemic agents with ability to inhibit lipid peroxidation. 1,3-Benzoxathioles (9 and 22), phenoxypentanoic acid (34), phenoxypentanol (35a), phenoxynonanol (35b), phenylchloropropionic acid having a chromanyl group (25), and a thiazolidine compound (27) derived from 25, all having a hindered phenol group, were prepared and examined. Compound 27 showed the expected biological properties in vivo and in vitro without any liver weight increase. Biological activities of the analogous thiazolidine compounds, 43-58, were compared. Thus, (+/-)-5-[4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]- benzyl]-2,4-thiazolidinedione (27) (CS-045) was found to have all of our expected properties and was selected as a candidate for further development as a hypoglycemic and hypolipidemic agent.

  DOI：

  10.1021/jm00122a022
• 作为产物：
  描述：

  1-特戊酰-2,3,5-三甲基氢醌 在 咪唑 、 氢氧化钾 、 sodium hydroxide 、 四丁基硫酸氢铵 、 sodium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 3-<4-<(tert-Butyldimethylsilyl)oxy>-2,3,5-trimethylphenoxy>propyl bromide
  参考文献：
  名称：

  Studies on hindered phenols and analogs. 1. Hypolipidemic and hypoglycemic agents with ability to inhibit lipid peroxidation

  摘要：

  A series of hindered phenols were investigated as hypolipidemic and/or hypoglycemic agents with ability to inhibit lipid peroxidation. 1,3-Benzoxathioles (9 and 22), phenoxypentanoic acid (34), phenoxypentanol (35a), phenoxynonanol (35b), phenylchloropropionic acid having a chromanyl group (25), and a thiazolidine compound (27) derived from 25, all having a hindered phenol group, were prepared and examined. Compound 27 showed the expected biological properties in vivo and in vitro without any liver weight increase. Biological activities of the analogous thiazolidine compounds, 43-58, were compared. Thus, (+/-)-5-[4-[(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methoxy]- benzyl]-2,4-thiazolidinedione (27) (CS-045) was found to have all of our expected properties and was selected as a candidate for further development as a hypoglycemic and hypolipidemic agent.

  DOI：

  10.1021/jm00122a022

文献信息

• Selective Scavenging Property of the Indole Moiety for the Nitrating Species of Peroxynitrite
  作者：Hidehiko Nakagawa、Mitsuko Takusagawa、Hiromi Arima、Kumiko Furukawa、Takeshi Kinoshita、Toshihiko Ozawa、Nobuo Ikota

  DOI：10.1248/cpb.52.146

  日期：——

  The inhibitory effect on tyrosine nitration and oxidation of peroxynitrite was evaluated for more than 40 reagents including natural and synthetic compounds, and the inhibiting efficiency of each compound for nitration was compared with that for oxidation, to characterize its property as a peroxynitrite scavenger. In the presence of various concentrations of testing compounds, the nitrating and oxidizing activities were measured by monitoring the formation of 3-nitrotyrosine and dityrosine with an HPLC-UV-fluorescence detector. The IC50 values for nitration and oxidation were determined, and the ratio of these two IC50 values was calculated for each compound. Although the IC50 values varied from compound to compound, it was revealed that the ratio of two IC50 values (IC50 for oxidation/IC50 for nitration) was 1 in almost all the compounds tested, except five indole derivatives (L-tryptophan, melatonin, 5-methoxytryptamine, tryptamine, and tetrahydro-beta-carboline) and one synthetic selenium-containing compound ((2R,3R,4S)-2-amino-3,4-dihydroxy-5-phenylselenopentan-1-ol, ADPP). The indole derivatives showed a specific inhibitory effect on tyrosine nitration without affecting the oxidation. ADPP was confirmed to have a preferable inhibitory activity for tyrosine oxidation. It was suggested that compounds showing an IC50 value ratio of 1 scavenged the common species for nitration and oxidation, while the indole derivatives and ADPP preferably scavenged the nitrating and oxidizing species, respectively. From a stopped flow study, it was also revealed that the nitrotyrosine formation was relatively slow, unlike an OH radical reaction. These results imply that the peroxynirite reaction at least partly proceeds through specific species for nitration.

  评估了 40 多种试剂（包括天然和合成化合物）对酪氨酸硝化和过亚硝酸氧化的抑制作用，并比较了每种化合物对硝化和氧化的抑制效率，以确定其作为过亚硝酸清除剂的特性。在不同浓度的测试化合物存在的情况下，通过 HPLC-UV 荧光检测器监测 3-硝基酪氨酸和二酪氨酸的形成，测量硝化和氧化活性。测定了硝化和氧化作用的 IC50 值，并计算了每种化合物这两个 IC50 值的比值。虽然不同化合物的 IC50 值各不相同，但结果显示，几乎所有测试化合物的两个 IC50 值之比（氧化 IC50 值/硝化 IC50 值）都是 1、除了五种吲哚衍生物（L-色氨酸、褪黑素、5-甲氧基色胺、色胺和四氢-beta-咔啉）和一种合成含硒化合物（(2R,3R,4S)-2-氨基-3,4-二羟基-5-苯基硒戊-1-醇，ADPP）。这些吲哚衍生物对酪氨酸硝化有特异性抑制作用，但不影响氧化作用。经证实，ADPP 对酪氨酸氧化具有较好的抑制活性。研究表明，IC50 值比值为 1 的化合物可以清除硝化和氧化的常见物种，而吲哚衍生物和 ADPP 则分别优先清除硝化和氧化物种。停流研究还显示，与羟自由基反应不同，硝基酪氨酸的形成相对缓慢。这些结果表明，过氧腈反应至少有一部分是通过特定的硝化物种进行的。