4-((t-butyldimethylsilyl)oxy)-2,3,5-trimethylphenol | 112136-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-((t-butyldimethylsilyl)oxy)-2,3,5-trimethylphenol
• 英文别名: 4-(tert-butyldimethylsilyloxy)-2,3,5-trimethylphenol；4-tertbutyldimethylsilyloxy-3,5,6-trimethylphenol；4-[Tert-butyl(dimethyl)silyl]oxy-2,3,5-trimethylphenol
• CAS: 112136-00-2
• 化学式: C₁₅H₂₆O₂Si
• 分子量: 266.456
• InChiKey: IWNOJVVYNMBASW-UHFFFAOYSA-N

物化性质

• 沸点：
  338.8±30.0 °C(Predicted)
• 密度：
  0.954±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-((t-butyldimethylsilyl)oxy)-2,3,5-trimethylphenol 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 四丁基氟化铵 、 四丁基硫酸氢铵 、 sodium hydride 、 sodium carbonate 、 溶剂黄146 、 二异丙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.75h， 生成 5-(4-Hydroxy-2,3,5-trimethylphenoxy)-2,2-dimethylnonanol
  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：

  三甲基氢醌 在 吡啶 、 咪唑 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.42h， 生成 4-((t-butyldimethylsilyl)oxy)-2,3,5-trimethylphenol
  参考文献：
  名称：

  [EN] BIOISPIRED PROTEASOME ACTIVATORS WITH ANTIAGEING ACTIVITY
  [FR] ACTIVATEURS BIO-INSPIRÉS DES PROTÉASOMES AYANT UNE ACTIVITÉ ANTI-ÂGE

  摘要：

  本发明涉及新型生物启发的混合化合物，其化学式为I，作为蛋白酶体激活剂并具有抗衰老活性，以及其合成方法。这些混合化合物将羟基酪醇和天然抗氧化维生素E或其生物同系物的结构特征结合在一个分子支架中。化合物I的结构包括结构蛋白酶体激活剂（通过立体化学相互作用激活），可用于生产抗衰老产品，如化妆品制剂。此外，它们可以在蛋白酶体被下调的情况和疾病中使用，以及用作蛋白酶体激活控制化合物。

  公开号：

  WO2019171088A1

文献信息

• A Straightforward Hetero-Diels-Alder Approach to (2-<i>ambo</i>,4′<i>R</i>,8′<i>R</i>)-α/β/γ/δ-4-Thiatocopherol
  作者：Stefano Menichetti、Riccardo Amorati、Maria Grazia Bartolozzi、Gian Franco Pedulli、Antonella Salvini、Caterina Viglianisi

  DOI：10.1002/ejoc.200901493

  日期：2010.4

  A simple and original inverse electron demand hetero-Diels–Alder reaction has been successfully applied to the synthesis of (2-ambo,4′R,8′R)-α/β/γ/δ-4-thiatocopherol. Commercially available methyl hydroquinones and (2E,7R,11R)-(+)-phytol were exploited for the preparation of the ortho-thioquinones, acting as electron-poor dienes, and of the proper 1,3-diene used as dienophile, respectively. The benzoxathiine

  一个简单而原始的逆电子需求杂-Diels-Alder反应已成功应用于(2-ambo,4'R,8'R)-α/β/γ/δ-4-硫代生育酚的合成。市售的甲基氢醌和 (2E,7R,11R)-(+)-phytol 分别用于制备邻硫醌类化合物（用作缺电子二烯）和适当的 1,3-二烯类用作亲二烯体. 在完全控制区域和化学选择性的情况下，获得了具有所需的类生育酚骨架的苯并沙西因环加合物。与维生素 E 的相应天然成分的抗氧化活性相比，4-硫代生育酚的抗氧化活性被测量和合理化。
• [EN] BIOISPIRED PROTEASOME ACTIVATORS WITH ANTIAGEING ACTIVITY<br/>[FR] ACTIVATEURS BIO-INSPIRÉS DES PROTÉASOMES AYANT UNE ACTIVITÉ ANTI-ÂGE
  申请人：NATIONAL HELLENIC RES FOUNDATION

  公开号：WO2019171088A1

  公开（公告）日：2019-09-12

  The present invention relates to novel bio-inspired hybrid compounds of formula I which act as proteasome activators and exhibit anti-ageing activity, as well as methods for their synthesis. These hybrid compounds combine the structural features of hydroxytyrosol and the natural antioxidant vitamin E or its bioisosteres in one molecular scaffold. The compounds of formula I, which include structural proteasome activators (activation by stereochemical interaction), can be used in the production of anti-ageing products, such as cosmetic preparations. Additionally, they can be used in conditions and diseases where the proteasome is down-regulated, as well as proteasome-activation control compounds.

  本发明涉及新型生物启发的混合化合物，其化学式为I，作为蛋白酶体激活剂并具有抗衰老活性，以及其合成方法。这些混合化合物将羟基酪醇和天然抗氧化维生素E或其生物同系物的结构特征结合在一个分子支架中。化合物I的结构包括结构蛋白酶体激活剂（通过立体化学相互作用激活），可用于生产抗衰老产品，如化妆品制剂。此外，它们可以在蛋白酶体被下调的情况和疾病中使用，以及用作蛋白酶体激活控制化合物。
• Studies on hindered phenols and analogs. 1. Hypolipidemic and hypoglycemic agents with ability to inhibit lipid peroxidation
  作者：Takao Yoshioka、Takashi Fujita、Tsutomu Kanai、Yuichi Aizawa、Tomoyuki Kurumada、Kazuo Hasegawa、Hiroyoshi Horikoshi

  DOI：10.1021/jm00122a022

  日期：1989.2

  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.