N-(4-(triisopropylsilyloxy)phenyl)acetamide | 1445875-27-3

• 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: N-(4-(triisopropylsilyloxy)phenyl)acetamide
• 英文别名: N-[4-tri(propan-2-yl)silyloxyphenyl]acetamide
• CAS: 1445875-27-3
• 化学式: C₁₇H₂₉NO₂Si
• 分子量: 307.508
• InChiKey: UJSSRJBJDFHLGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-(triisopropylsilyloxy)phenyl)acetamide 在 cerium (IV) sulfate tetrahydrate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 对乙酰氨基酚
  参考文献：
  名称：

  四水合硫酸铈（IV）：THP，MOM和BOM醚的催化和高度化学选择性脱保护

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2013.10.117
• 作为产物：
  描述：

  三异丙基氯硅烷 、 对乙酰氨基酚 在 咪唑 作用下， 以46%的产率得到N-(4-(triisopropylsilyloxy)phenyl)acetamide
  参考文献：
  名称：

  Taming of a Superbase for Selective Phenol Desilylation and Natural Product Isolation

  摘要：

  Hydroxyl moieties are highly prevalent in natural products. We previously reported a chemoselective strategy for enrichment of hydroxyl-functionalized molecules by formation of a silyl ether bond to a resin. To generate smaller pools of molecules for analysis, we developed cleavage conditions to promote stepwise release of phenolic silyl ethers followed by aliphatic silyl ethers with a "tamed" version of the superbase 1,1,3,3-tetramethylguanadine. We demonstrate this as a general strategy for selective deprotection of phenolic silyl ethers under neutral conditions at room temperature.

  DOI：

  10.1021/jo4010298

文献信息

• 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
• CHEMOSELECTIVE ENRICHMENT FOR COMPOUND ISOLATION
  申请人：Indiana University Research and Technology Corporation

  公开号：US20140107328A1

  公开（公告）日：2014-04-17

  Chemoselective isolation of aliphatic hydroxyl group-containing and aromatic hydroxyl group-containing compounds is accomplished via formation of polymeric siloxyl ethers. Chemoselective release of aliphatic hydroxyl group-containing and aromatic hydroxyl group-containing compounds from polymeric siloxyl reagents is described.

  通过形成聚合硅氧烷醚，可以实现对含有脂肪烃羟基和芳香族羟基化合物的化学选择性分离。本文描述了从聚合硅氧烷试剂中选择性释放含有脂肪烃羟基和芳香族羟基化合物的化学选择性。
• Selective deprotection of TBDMS alkyl ethers in the presence of TIPS or TBDPS phenyl ethers by catalytic CuSO4·5H2O in methanol
  作者：Davir González-Calderón、Luis J. Benítez-Puebla、Carlos A. González-González、Salomón Assad-Hernández、Aydeé Fuentes-Benítez、Erick Cuevas-Yáñez、David Corona-Becerril、Carlos González-Romero

  DOI：10.1016/j.tetlet.2013.07.074

  日期：2013.9

  TBDMS alkyl ethers are efficiently cleaved to the corresponding hydroxyl compounds upon heating (conventional or microwave) in methanol solution containing 20 mol % CuSO4 center dot 5H(2)O. Intramolecular chemoselective experiments showed that TBDMS alkyl ethers are selectively cleaved in the presence of TIPS or TBDPS aryl ethers. Competition experiments also showed that TBDMS alkyl ethers were selectively cleaved in the presence of TBDPS alkyl ethers. (C) 2013 Elsevier Ltd. All rights reserved.
• 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。
• Taming of a Superbase for Selective Phenol Desilylation and Natural Product Isolation
  作者：Darci J. Trader、Erin E. Carlson

  DOI：10.1021/jo4010298

  日期：2013.7.19

  Hydroxyl moieties are highly prevalent in natural products. We previously reported a chemoselective strategy for enrichment of hydroxyl-functionalized molecules by formation of a silyl ether bond to a resin. To generate smaller pools of molecules for analysis, we developed cleavage conditions to promote stepwise release of phenolic silyl ethers followed by aliphatic silyl ethers with a "tamed" version of the superbase 1,1,3,3-tetramethylguanadine. We demonstrate this as a general strategy for selective deprotection of phenolic silyl ethers under neutral conditions at room temperature.