苄基(2-羟乙基)氨基甲酸叔丁酯 | 121496-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苄基(2-羟乙基)氨基甲酸叔丁酯
• 英文名称: N-(tert-butoxycarbonyl)-N-benzylethanolamine
• 英文别名: tert-butyl benzyl(2-hydroxyethyl)carbamate；N-benzyl-N-(2-hydroxy-ethyl)-carbamic acid tert-butyl ester；Tert-butyl N-benzyl-N-(2-hydroxyethyl)carbamate
• CAS: 121496-39-7
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: LBYKHAZJINITAL-UHFFFAOYSA-N

物化性质

• 沸点：
  372.9±31.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温下应存放在干燥且密封的容器中。

反应信息

• 作为反应物：
  描述：

  苄基(2-羟乙基)氨基甲酸叔丁酯 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 N-(2-(2-甲氧基苯氧基)乙基)苄胺盐酸盐
  参考文献：
  名称：

  Studies toward the Discovery of the Next Generation of Antidepressants. 3. Dual 5-HT_1A and Serotonin Transporter Affinity within a Class of N-Aryloxyethylindolylalkylamines

  摘要：

  N-Aryloxylethylindolealkylamines (5) having dual 5-HT transporter and 5-HT1A affinity are described. These compounds represent truncated analogues of our previously reported piperidinyl derivatives (3). Compounds in this investigation were found to have more similar affinities and functional activities for the 5-HT1A receptor and 5-HT transporter. Though 5-HT1A antagonism is not consistently observed throughout series 5, several molecular features were found to be essential to obtain high and balanced activities. The proper placement of a heteroatom in the aryl ring and the length of the linkage used to tether the indole moiety had significant influence on 5-HT1A and 5-HT transporter affinities. Introduction of a halogen into the aryl ring usually lowered intrinsic activity and in some cases led to full 5-HT1A antagonists. Compounds 33 and 34 were observed to be full 5-HT1A antagonists with K-i values of approximately 30 nM for the 5-HT1A receptor and K-i values of 5 and 0.5 nM for the 5-HT transporter, respectively. Unfortunately, similar to our previous series (3), compounds in this report also had high affinity for the alpha(1) receptor.

  DOI：

  10.1021/jm0304010
• 作为产物：
  描述：

  溴甲苯 在 lithium aluminium tetrahydride 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙腈 为溶剂， 反应 54.0h， 生成 苄基(2-羟乙基)氨基甲酸叔丁酯
  参考文献：
  名称：

  通过合成，生物学评估和基于结构的建模发现新的人类凝血因子XIa（FXIa）抑制剂

  摘要：

  XIa因子（FXIa）是一种在凝血机制内在途径起始的最早阶段被激活的酶。在这项研究中，我们试图基于基于结构的分子模型发现一种新的FXIa抑制剂。我们发现化合物16表现出令人满意的预测特性，同时保持与FX1a的重要结合相互作用。

  DOI：

  10.1002/bkcs.10831

文献信息

• 1,1,1,3,3,3-Hexafluoroisopropanol: A Recyclable Organocatalyst for<i>N</i>-Boc Protection of Amines
  作者：Akbar Heydari、Samad Khaksar、Mahmood Tajbakhsh

  DOI：10.1055/s-2008-1067272

  日期：2008.10

  A simple and efficient protocol for the chemoselective mono-N-Boc protection of various structurally diverse amines with di-tert-butyl dicarbonate using 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as solvent and catalyst is described. The catalyst can be readily separated from the reaction products and recovered for direct reuse. No competitive side reactions such as formation of isocyanate, urea, and N,N-di-Boc were observed. α-Amino alcohols afforded the N-Boc derivatives without oxazolidinone formation.

  描述了一种简单且高效的化学选择性单-N-Boc保护多种结构多样性胺类的方法，使用二叔丁基二碳酸酯和1,1,1,3,3,3-六氟异丙醇（HFIP）作为溶剂和催化剂。催化剂可以轻易地从反应产物中分离并回收，以便直接重复使用。未观察到异氰酸酯、脲和N,N-二-Boc等竞争性副反应。α-氨基醇类在未形成恶唑烷酮的情况下获得了N-Boc衍生物。
• Protic ionic liquid [TMG][Ac] as an efficient, homogeneous and recyclable catalyst for Boc protection of amines
  作者：Jafar Akbari、Akbar Heydari、Leila Ma’mani、Seyed Hassan Hosseini

  DOI：10.1016/j.crci.2009.10.003

  日期：2010.5

  Résumé An efficient and practical protocol for the chemoselective N-Boc protection of various structurally different aryl, aliphatic and heterocyclic amines was carried out with (Boc)2O using protic 1, 1, 3, 3-tetra-methylguanidinium acetate (10 mol%) as recyclable catalyst under solvent free condition at ambient temperature. No competitive side reactions (isocyanate, urea and N, N-di-Boc) were observed. α-Amino alcohols afforded the N-Boc-derivative without oxazolidinone formation.

  简历 一种高效且实用的化学选择性N-Boc保护各种结构不同的芳基、脂肪族和杂环胺的协议，通过在无溶剂条件下使用质子化的1,1,3,3-四甲基胍乙酸盐（10 mol%）作为可回收催化剂，在室温下使用(Boc)2O进行。未观察到竞争性的副反应（异氰酸酯、脲和N,N-二Boc）。α-氨基醇提供了N-Boc衍生物而不形成噁唑烷酮。
• Rice husk: Introduction of a green, cheap and reusable catalyst for the protection of alcohols, phenols, amines and thiols
  作者：Farhad Shirini、Somayeh Akbari-Dadamahaleh、Ali Mohammad-Khah、Ali-Reza Aliakbar

  DOI：10.1016/j.crci.2013.01.018

  日期：2014.2

  eco-friendly protocol for the chemoselective protection of benzylic and primary and less hindered secondary aliphatic alcohols and phenols as trimethylsilyl ethers and different types of amines as N-tert-butylcarbamates is developed using rice husk (RiH) as the catalyst. This reagent is also able to catalyze the acetylation of alcohols, phenols, thiols and amines with acetic anhydride. Easy work-up, relatively

  摘要 以稻壳 (RiH) 为原料，开发了一种温和、高效、环保的方案，用于化学选择性保护苄基和伯和受阻较小的仲脂肪醇和酚作为三甲基甲硅烷基醚以及不同类型的胺作为 N-叔丁基氨基甲酸酯。催化剂。该试剂还能够催化醇、酚、硫醇和胺与乙酸酐的乙酰化反应。该方法的显着特点是后处理简单、反应时间相对较短、收率高、成本低、催化剂的可用性和可重复使用性是该方法的显着特点，可被认为是保护醇、酚的最佳和通用方法之一、硫醇和胺。此外，
• Discovery of orally efficacious RORγt inverse agonists. Part 2: Design, synthesis, and biological evaluation of novel tetrahydroisoquinoline derivatives
  作者：Mitsunori Kono、Tsuneo Oda、Michiko Tawada、Takashi Imada、Yoshihiro Banno、Naohiro Taya、Tetsuji Kawamoto、Hidekazu Tokuhara、Yoshihide Tomata、Naoki Ishii、Atsuko Ochida、Yoshiyuki Fukase、Tomoya Yukawa、Shoji Fukumoto、Hiroyuki Watanabe、Keiko Uga、Akira Shibata、Hideyuki Nakagawa、Mikio Shirasaki、Yasushi Fujitani、Masashi Yamasaki、Junya Shirai、Satoshi Yamamoto

  DOI：10.1016/j.bmc.2017.12.008

  日期：2018.1

  A series of tetrahydroisoquinoline derivatives were designed, synthesized, and evaluated for their potential as novel orally efficacious retinoic acid receptor-related orphan receptor-gamma t (RORγt) inverse agonists for the treatment of Th17-driven autoimmune diseases. We carried out cyclization of the phenylglycinamide core by structure-based drug design and successfully identified a tetrahydroisoquinoline

  设计，合成和评估了一系列四氢异喹啉衍生物作为新型口服有效的视黄酸受体相关的孤儿受体-γt（RORγt）反向激动剂的潜力，用于治疗Th17驱动的自身免疫性疾病。我们通过基于结构的药物设计对苯基甘氨酰胺核心进行环化，并成功鉴定出具有良好生化结合和细胞报道分子活性的四氢异喹啉羧酸衍生物14。有趣的是，羧酸系链和中心稠合双环的结合对于优化PK性能至关重要，化合物14显示出明显改善的PK分布。羧酸酯系链的连续优化导致发现化合物15具有增强的反向激动活性和出色的PK分布。在IL23诱导的基因表达分析中，用化合物15口服治疗小鼠有力且剂量依赖性地抑制了IL-17A的产生。
• ZnO Nanorods as an Efficient and Heterogeneous Catalyst for N-Boc Protection of Amines and Amine Derivatives
  作者：Azita Nouri、Jafar Akbari、Akbar Heydari、Arezu Nouri

  DOI：10.2174/157017811794557859

  日期：2011.1.1

  An efficient ZnO nano catalyst, which was readily prepared from Zn(CH3CO2)2, 2H2O and PVP by a chemical solution approach has successfully catalyzed N-tertbutoxy carbonylation of amines. The ZnO nanorods were successful and gave promising results for highly active and chemoselective as well as easily recyclable catalyst for the NBoc protection reaction of a wide variety of amines. The catalyst could be easily recycled for five times without noticeable decrease in catalytic activity. The ZnO nanocatalyst was characterized with XRD and SEM.

  一种高效的ZnO纳米催化剂，通过化学溶液法制备，原料为Zn(CH3CO2)2·2H2O和PVP，成功催化了胺的N-叔丁氧羰基化反应。ZnO纳米棒作为催化剂表现出色，为各种胺的NBoc保护反应提供了高活性、化学选择性且易于回收的催化剂，并显示出良好的结果。该催化剂可轻松回收利用五次，催化活性未见明显下降。通过XRD和SEM对ZnO纳米催化剂进行了表征。