(3-(tert-butyldiphenylsilyloxy)phenyl)methanol | 171906-76-6

• 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: (3-(tert-butyldiphenylsilyloxy)phenyl)methanol
• 英文别名: [3-[Tert-butyl(diphenyl)silyl]oxyphenyl]methanol；[3-[tert-butyl(diphenyl)silyl]oxyphenyl]methanol
• CAS: 171906-76-6
• 化学式: C₂₃H₂₆O₂Si
• 分子量: 362.544
• InChiKey: OLDPFEUNIXHMGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  (3-(tert-butyldiphenylsilyloxy)phenyl)methanol 在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 48.0h， 以86%的产率得到3-tert-butyldiphenylsilyloxybenzyl bromide
  参考文献：
  名称：

  Development of a Novel Hapten for Radioimmunoassay of the Lignan, Enterolactone in Plasma (Serum). Total Synthesis of (±)-trans-5-Carboxymethoxyenterolactone and Several Analogues

  摘要：

  A recently developed method for the analysis of the mammalian lignan, enterolactone 1, is based on time-resolved fluoroimmunoassay (TR-FIA) using an europium chelate as a label. This RIA utilizes enterolactone derivatives carrying a carboxylic acid appendage for the production of antiserum and tracer. The synthesis of 5-carboxymethoxyenterolactone 6 and analogues 5, 7 and 8 is described, and their suitability for the method are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00078-8
• 作为产物：
  描述：

  3-((tert-butyldiphenylsilyl)oxy)benzaldehyde 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以99%的产率得到(3-(tert-butyldiphenylsilyloxy)phenyl)methanol
  参考文献：
  名称：

  Development of a Novel Hapten for Radioimmunoassay of the Lignan, Enterolactone in Plasma (Serum). Total Synthesis of (±)-trans-5-Carboxymethoxyenterolactone and Several Analogues

  摘要：

  A recently developed method for the analysis of the mammalian lignan, enterolactone 1, is based on time-resolved fluoroimmunoassay (TR-FIA) using an europium chelate as a label. This RIA utilizes enterolactone derivatives carrying a carboxylic acid appendage for the production of antiserum and tracer. The synthesis of 5-carboxymethoxyenterolactone 6 and analogues 5, 7 and 8 is described, and their suitability for the method are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00078-8

文献信息

• Cerium(IV) sulfate tetrahydrate: a catalytic and highly chemoselective deprotection of THP, MOM, and BOM ethers
  作者：Davir González-Calderón、Carlos A. González-González、Aydeé Fuentes-Benítez、Erick Cuevas-Yáñez、David Corona-Becerril、Carlos González-Romero

  DOI：10.1016/j.tetlet.2013.10.117

  日期：2013.12

  methoxymethyl (MOM), and benzyloxymethyl (BOM) phenyl/alkyl ethers were efficiently cleaved to the corresponding parent hydroxyl compounds in good yields using catalytic amounts of Ce(SO4)2·4H2O by microwave-assisted or conventional heating in methanol solution. Intramolecular and competitive experiments demonstrated the chemoselective deprotection of THP ethers in the presence of triisopropylsilyl (TIPS)

  四氢吡喃基（THP），甲氧基甲基（MOM）和苄氧基甲基（BOM）苯基/烷基醚通过微波辅助催化作用或催化量的Ce（SO 4）2 ·4H 2 O被有效地裂解成相应的母体羟基化合物。常规在甲醇溶液中加热。分子内和竞争实验表明，在三异丙基甲硅烷基（TIPS）和叔丁基二苯基甲硅烷基（TBDPS）苯基醚存在下，THP醚的化学选择性脱保护。
• Studies of selective Boc removal in the presence of silyl ethers
  作者：Florine Cavelier、Christine Enjalbal

  DOI：10.1016/0040-4039(96)01070-2

  日期：1996.7

  The selective removal of N-Boc protection can be obtained in the presence of either TBDMS or TBDPS ethers. On the basis of promising results from the literature, we first tried sonication, that failed, whereas the exclusive cleavage of the Boc group was successfully achieved by a saturated solution of HCl in ethyl acetate.

  N-Boc保护的选择性去除可以在TBDMS或TBDPS醚存在下获得。基于文献中令人鼓舞的结果，我们首先尝试了超声处理，但失败了，而Boc基团的唯一裂解是通过HCl在乙酸乙酯中的饱和溶液成功实现的。
• A Novel Chemoselective Cleavage of (<i>tert</i>-Butyl)(dimethyl)silyl (TBS) Ethers Catalyzed by Ce(SO₄)₂⋅4 H₂O
  作者：Davir González-Calderón、Carlos A. González-González、Aydeé Fuentes-Benítez、Erick Cuevas-Yáñez、David Corona-Becerril、Carlos González-Romero

  DOI：10.1002/hlca.201300354

  日期：2014.7

  (tert‐Butyl)(dimethyl)silyl (tBuMe2Si; TBS) phenyl/alkyl ethers were efficiently cleaved to the corresponding parent hydroxy compounds in good yields using catalytic amounts of Ce(SO4)2⋅4 H2O by microwave‐assisted or conventional heating in MeOH. Intramolecular and competitive experiments demonstrated the chemoselective deprotection of TBS ethers in the presence of triisopropylsilyl (iPr3Si; TIPS)

  （叔丁基）（二甲基）甲硅烷基（吨BuMe 2的Si; TBS）苯基/烷基醚得到有效切割而以良好的收率使用催化量的Ce的相应的亲本羟基化合物（SO 4）2 ⋅4ħ 2 ö通过微波辅助或常规在MeOH中加热。分子内和竞争实验表明，在三异丙基甲硅烷基（i Pr 3 Si; TIPS）和（叔丁基）（二苯基）甲硅烷基（t BuPh 2 Si; TBDPS）醚存在下，TBS醚的化学选择性脱保护。
• Aluminium Chloride Hexahydrate (AlCl₃ · 6H₂O): An Efficient, Facile, Mild, And Highly Chemoselective Catalytic Deprotection of Tert-Butyldimethylsilyl (TBS) Ethers
  作者：Davir González-Calderón、Luis J. Benitez-Puebla、Carlos A. Gonzalez-Gonzalez、Marco A. Garcia-Eleno、Aydeé Fuentes-Benitez、Erick Cuevas-Yañez、David Corona-Becerril、Carlos González-Romero

  DOI：10.1080/00397911.2013.851243

  日期：2014.5.3

  Abstract tert-Butyldimethylsilyl (TBS) phenyl / alkyl ethers were cleaved to the corresponding efficiently parent hydroxyl compounds in good yields using catalytic amounts of AlCl3 · 6H2O by conventional or microwave-assisted heating in methanol or isopropanol solution. Intramolecular and competitive experiments demonstrated the chemoselective deprotection of TBS ethers in the presence of triisopropylsilyl

  摘要 使用催化量的 AlCl3·6H2O 通过常规或微波辅助加热在甲醇或异丙醇溶液中，叔丁基二甲基甲硅烷基 (TBS) 苯基/烷基醚以良好的产率裂解为相应的有效母体羟基化合物。分子内和竞争实验证明了在三异丙基甲硅烷基和叔丁基二苯基甲硅烷基醚存在下 TBS 醚的化学选择性脱保护。图形概要
• Development of a Novel Hapten for Radioimmunoassay of the Lignan, Enterolactone in Plasma (Serum). Total Synthesis of (±)-trans-5-Carboxymethoxyenterolactone and Several Analogues
  作者：Taru Mäkelä、Jorma Matikainen、Kristiina Wähälä、Tapio Hase

  DOI：10.1016/s0040-4020(00)00078-8

  日期：2000.3

  A recently developed method for the analysis of the mammalian lignan, enterolactone 1, is based on time-resolved fluoroimmunoassay (TR-FIA) using an europium chelate as a label. This RIA utilizes enterolactone derivatives carrying a carboxylic acid appendage for the production of antiserum and tracer. The synthesis of 5-carboxymethoxyenterolactone 6 and analogues 5, 7 and 8 is described, and their suitability for the method are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.