4-[(tert-butyldimethylsilyl)oxy]aniline | 111359-74-1

• 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: 4-[(tert-butyldimethylsilyl)oxy]aniline
• 英文别名: 4-(tert-butyldimethylsilanyloxy)phenylamine；4-(t-butyldimethylsilyloxy)aniline；4-tert-butyldimethylsiloxyaniline；4-(tert-butyldimethylsilyloxy)benzenamine；4-(1,1,2,2-tetramethyl-1-silapropoxy)phenylamine；4-(tert-Butyldimethylsiloxy)aniline；4-[tert-butyl(dimethyl)silyl]oxyaniline
• CAS: 111359-74-1
• 化学式: C₁₂H₂₁NOSi
• 分子量: 223.39
• InChiKey: XSVKDCVIWOKXSX-UHFFFAOYSA-N

物化性质

• 沸点：
  273.2±23.0 °C(Predicted)
• 密度：
  0.954±0.06 g/cm3(Predicted)
• 保留指数：
  1575.7

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[(tert-butyldimethylsilyl)oxy]aniline 在 lithium acetate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以87%的产率得到对氨基苯酚
  参考文献：
  名称：

  LiOAc-Catalyzed Chemoselective Deprotection of Aryl Silyl Ethers under Mild Conditions

  摘要：

  An efficient and chemoselective deprotection protocol for aryl silyl ethers using LiOAc as a bifunctional Lewis acid-Lewis base catalyst was described. Acetates, epoxides, and aliphatic silyl ethers were preserved, whereas aryl TBS and TBDPS ethers can be differentiated.

  DOI：

  10.1021/jo802472s
• 作为产物：
  描述：

  4-(叔丁基二甲基硅氧)环己酮 在 一水合肼 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 20.0~160.0 ℃ 、101.33 kPa 条件下， 反应 3.5h， 以50%的产率得到4-[(tert-butyldimethylsilyl)oxy]aniline
  参考文献：
  名称：

  利用肼通过负载钯催化的无受体脱氢芳构化选择性合成初级苯胺

  摘要：

  通过在羟基磷灰石负载的 Pd 纳米颗粒催化剂 (Pd/HAP) 存在下利用肼 (N 2 H 4 ) 作为氮源，可以通过无受体脱氢芳构化从环己酮选择性地合成各种伯苯胺。N 2 H 4的强亲核性和腙中间体的稳定性可以有效抑制不需要的次级苯胺副产物的形成。

  DOI：

  10.1039/d1cc01686e

文献信息

• [EN] METHODS AND COMPOUNDS FOR THE TREATMENT OF GENETIC DISEASE<br/>[FR] PROCÉDÉS ET COMPOSÉS POUR LE TRAITEMENT D'UNE MALADIE GÉNÉTIQUE
  申请人：DESIGN THERAPEUTICS INC

  公开号：WO2021158707A1

  公开（公告）日：2021-08-12

  The present disclosure relates to compounds and methods for modulating the expression of dmpk, and treating diseases and conditions in which dmpk plays an active role. The compound can be a transcription modulator molecule having a first terminus, a second terminus, and oligomeric backbone, wherein: a) the first terminus comprises a DNA-binding moiety capable of noncovalently binding to a nucleotide repeat sequence CAG or CTG; b) the second terminus comprises a protein-binding moiety binding to a regulatory molecule that modulates an expression of a gene comprising the nucleotide repeat sequence CAG or CTG; and c) the oligomeric backbone comprising a linker between the first terminus and the second terminus.

  本公开涉及化合物和方法，用于调节dmpk的表达，并治疗dmpk发挥积极作用的疾病和病况。该化合物可以是一种转录调节分子，具有第一末端、第二末端和寡聚骨架，其中：a）第一末端包括一种DNA结合基团，能够非共价结合到核苷酸重复序列CAG或CTG；b）第二末端包括结合到调节分子的蛋白结合基团，该调节分子调节包含核苷酸重复序列CAG或CTG的基因的表达；c）寡聚骨架包括连接第一末端和第二末端的连接物。
• Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C–Ethylene System and Its Application to Indole Synthesis
  作者：Katsumi Maeda、Ryosuke Matsubara、Masahiko Hayashi

  DOI：10.1021/acs.orglett.0c04056

  日期：2021.3.5

  The synthesis of anilines and indoles from cyclohexanones using a Pd/C–ethylene system is reported. A simple combination of NH4OAc and K2CO3 under nonaerobic conditions was found to be the most suitable to perform this reaction. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.

  据报道，使用Pd / C-乙烯系统可从环己酮合成苯胺和吲哚。发现在无氧条件下简单的NH 4 OAc和K 2 CO 3组合最适合进行该反应。环己酮和乙烯之间的氢转移产生了所需的产物。该反应可耐受起始环己酮上的各种取代。
• Pd-Catalyzed Silicon Hydride Reductions of Aromatic and Aliphatic Nitro Groups
  作者：Ronald J. Rahaim、Robert E. Maleczka

  DOI：10.1021/ol052120n

  日期：2005.10.1

  [reaction: see text] Room-temperature reduction of aromatic nitro groups to amines can be accomplished in high yield, with wide functional group tolerance and short reaction times (30 min) using a combination of palladium(II) acetate, aqueous potassium fluoride, and polymethylhydrosiloxane (PMHS). Replacing PMHS/KF with triethylsilane allows aliphatic nitro groups to be reduced to their hydroxylamines.

  [反应：参见正文]使用乙酸钯（II），氟化钾水溶液，和聚甲基氢硅氧烷（PMHS）。用三乙基硅烷代替PMHS / KF可使脂肪族硝基还原为羟胺。
• Chemoselective Hydrogenation Catalyzed by Pd on Spherical Carbon
  作者：Hiroyoshi Esaki、Tomohiro Hattori、Aya Tsubone、Satoko Mibayashi、Takao Sakata、Yoshinari Sawama、Yasunari Monguchi、Hidehiro Yasuda、Kazuto Nosaka、Hironao Sajiki

  DOI：10.1002/cctc.201300639

  日期：2013.12

  developed a highly chemoselective hydrogenation method using a novel palladium catalyst supported on spherical carbon (0.5 % Pd/SC). The 0.5 % Pd/SC exhibited a novel catalytic activity and could achieve the chemoselective hydrogenation of alkynes, alkenes, azides, nitro groups, and aliphatic O‐tert‐butyldimethylsilyl (TBS) ethers without hydrogenolysis of benzyl esters, benzyl ethers, nitriles, aromatic

  我们已经开发出了一种新型的高化学选择性氢化方法，该方法使用了一种新型的负载在球形碳（0.5％Pd / SC）上的钯催化剂。的0.5％的Pd / SC显示出新颖的催化活性，并可能实现炔烃，烯烃，叠氮化物，硝基基团的化学选择性氢化，以及脂族ö -叔丁基二甲基（TBS）醚无苄基酯，苄基醚，腈的氢解，芳族酮，N-碳苄氧基（N- Cbz）保护基和芳族O- TBS醚。
• Highly selective reduction of nitroarenes by iron(0) nanoparticles in water
  作者：Raju Dey、Nirmalya Mukherjee、Sabir Ahammed、Brindaban C. Ranu

  DOI：10.1039/c2cc30999h

  日期：——

  Highly selective reduction of nitroarenes has been achieved using iron metal nanoparticles in water at room temperature. A wide spectrum of reducible functionalities remained inert under the reaction conditions. During the reaction a change in shape of Fe nanoparticles was observed.

  在室温下的水相环境中，利用铁金属纳米颗粒实现了硝基芳烃的高度选择性还原。在反应条件下，广泛的还原性官能团保持惰性。反应过程中观察到了铁纳米颗粒形状的变化。