(2-叠氮基乙氧基)(叔丁基)二甲基硅烷 | 113274-21-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: (2-叠氮基乙氧基)(叔丁基)二甲基硅烷
• 英文名称: (2-azidoethoxy)(tert-butyl)dimethylsilane
• 英文别名: 2-azidoethoxy-tert-butyl-dimethylsilane
• CAS: 113274-21-8
• 化学式: C₈H₁₉N₃OSi
• 分子量: 201.344
• InChiKey: FWOURPSKAHEJOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-叠氮基乙氧基)(叔丁基)二甲基硅烷 在 二环己烷并-18-冠醚-6 、 potassium hydride 作用下， 以 乙醚 为溶剂， 反应 4.5h， 生成 1-<2-(tert-butyldimethylsiloxy)-ethyl>-3-carbethoxy-3-methyltriazene
  参考文献：
  名称：

  Novel cross-linking alkylating agents, 1-(2-chloroethyl)-3-methyl-3-acyltriazenes

  摘要：

  DOI：

  10.1021/jo00242a022
• 作为产物：
  描述：

  （2-溴乙氧基）-特丁基二甲基硅烷 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以100 %的产率得到(2-叠氮基乙氧基)(叔丁基)二甲基硅烷
  参考文献：
  名称：

  通过氢原子转移和自由基取代使 β-CF3-1,3-烯炔与烷基叠氮化物发散 [2 + n] 异环化

  摘要：

  铜促进的β-CF 3 -1,3-烯炔与烷基叠氮化物的发散分子间[2 + n ]杂环化，通过烷基驱动的HAT和自由基取代（C-C键形成）形成四至十元开发了饱和N-杂环。该方法能够通过三重态氮烯形成、自由基对氮原子进行芳基诱导或动力学控制的位点选择性官能化，将位置 2、3、4、5、6、7 或 8 处的远程 C(sp 3 )–H 键官能化。跨 C=C 键、HAT 和自由基取代级联进行加成，具有广泛的底物范围、出色的位点选择性以及生物活性分子易于后期衍生化的特点。最初的氘标记和对照实验揭示了通过氮烯形成和 HAT 的反应机制。

  DOI：

  10.1021/acs.orglett.3c04041

文献信息

• Substituted 1-(2-chloroethyl)-3-acyl-3-alkyltriazenes
  申请人：Bionetics Research, Inc.

  公开号：US04923970A1

  公开（公告）日：1990-05-08

  A substituted 1-(2-chloroethyl)-3-acyl-3-alkyltriazene of the formula: ##STR1## in which R.sub.1 is 1-oxoalkyl containing from two to eight carbon atoms, fluorinated 1-oxoalkyls containing from two to eight carbon atoms and substituted with up to three fluorine atoms, benzoyl, phenylacetyl, carboalkoxy containing from two to eight carbon atoms, fluorinated carboalkyl containing from two to eight carbon atoms and up to three fluorine atoms, carbophenoxy, N-phenyl aminocarbonyl, N-alkyl aminocarbonyl containing from two to eight carbon atoms, thiocarbamoyl, N-alkylthiocarbamoyls with from two to eight carbon atoms, N-phenylthiocarbamoyl, dialkylphosphonates in which the alkyl groups can be the same or different and each contains from one to seven carbon atoms, phenylsulfonyl, and meta or para-substituted phenylsulfonyl in which the meta or para substituent is methyl, ethyl, methoxy, ethoxy, fluoro and chloro; and R.sub.2 is indepedently alkyl containing from one to seven carbon atoms, fluoroalkyl containing from two to seven carbon atoms and from one to three fluorine atoms in which the .alpha. carbon of the fluoroalkyl group is not substituted with fluorine, benzyl, meta or para-substituted benzyl in which the meta or para substituent is chloro, fluoro, and alkoxy with from one to three carbon atoms, alkenyl containing from two to seven carbon atoms, and alkynyl containing from two to seven carbon atoms, useful as antitumor agents.

  公式为：##STR1##，其中R.sub.1是1-氧代烷基，含有2至8个碳原子，含有最多三个氟原子的氟代1-氧代烷基，苯甲酰基，苯乙酰基，含有2至8个碳原子的羧基烷基，含有2至8个碳原子和最多三个氟原子的氟代羧基烷基，羰基苯氧基，N-苯基氨基甲酰基，含有2至8个碳原子的N-烷基氨基甲酰基，硫代氨基甲酰基，含有2至8个碳原子的N-烷基硫代氨基甲酰基，N-苯基硫代氨基甲酰基，二烷基磷酸酯，其中烷基基团可以相同也可以不同，每个含有1至7个碳原子，苯磺酰基，以及间位或对位取代的苯磺酰基，其中间位或对位取代基是甲基，乙基，甲氧基，乙氧基，氟和氯；R.sub.2是独立的烷基，含有1至7个碳原子，含有2至7个碳原子和1至3个氟原子的氟代烷基，其中氟代烷基群的α碳未被氟取代，苄基，间位或对位取代的苄基，其中间位或对位取代基是氯，氟和含有1至3个碳原子的烷氧基，含有2至7个碳原子的烯基，以及含有2至7个碳原子的炔基，作为抗肿瘤剂。
• Regioselective Intramolecular Dipolar Cycloaddition of Azides and Unsymmetrical Alkynes
  作者：Ryan A. Brawn、Morgan Welzel、Jason T. Lowe、James S. Panek

  DOI：10.1021/ol902681t

  日期：2010.1.15

  used in three-component propargylation reactions with aldehydes and silyl ethers to form syn-homopropargylic ethers that contain an imbedded azide. These materials then undergo thermally induced intramolecular 1,3-dipolar cycloaddition reactions, resulting in unique fused ring systems containing 1,2,3-triazoles. The ability to modify all three components of the reaction allows for expedient access to

  对映体富集的烯丙基硅烷用于与醛和甲硅烷基醚的三组分炔丙基化反应，以形成含有嵌入叠氮化物的顺-均炔基醚。然后这些材料经历热诱导的分子内 1,3-偶极环加成反应，产生含有 1,2,3-三唑的独特稠环系统。改变反应的所有三个组分的能力允许方便地获得含有显着结构和立体化学变化的化合物。
• A New Lead Identification Strategy: Screening an sp ³ ‐rich and Lead‐like Compound Library Composed of 7‐Azanorbornane Derivatives
  作者：Fumika Karaki、Sho Umemoto、Karin Ashizawa、Tomoya Oki、Noriko Sato、Takumi Ogino、Naoto Ishibashi、Ryoto Someya、Kanako Miyano、Shigeto Hirayama、Yasuhito Uezono、Hideaki Fujii

  DOI：10.1002/cmdc.201900398

  日期：2019.11.6

  have been pointed out, modern screening libraries are filled with planar, sp2 -rich components. Compounds that are sp3 -rich are difficult to synthesize, and thus we aimed to invent an efficient method to construct sp3 -rich libraries. By modifying sp3 -rich 7-azanorbornane scaffolds through click chemistry, we efficiently prepared a small set of compounds. These compounds were not only sp3 -rich, but

  尽管已经指出了富含sp3的，空间复杂的分子在药物开发中的优势，但现代筛选库中充满了富含sp2的平面成分。富含sp3的化合物难以合成，因此我们旨在发明一种构建富含sp3的文库的有效方法。通过点击化学修饰富含sp3的7-氮杂降冰片骨架，我们有效地制备了少量化合物。这些化合物不仅富含sp3，而且鉴于分子量和疏水性还具有足够的“铅样”性质。该文库的筛选试验提供了具有高命中率的弱κ阿片受体激动剂和生长激素促分泌素受体激动剂。这些结果表明7-氮杂硼烷骨架可能是“特权结构”。
• A Ru-catalyzed one-pot synthesis of homopropargylic amines from alkyl azides under photolytic conditions
  作者：Wook Jeong、Ji Hyung Lee、Jungjoon Kim、Won Jong Lee、Ju-Hwa Seong、Jaiwook Park、Young Ho Rhee

  DOI：10.1039/c4ra02941k

  日期：——

  new synthetic method for homopropargylic amines from alkyl azides is presented. A salient feature of this reaction is the involvement of N-unsubstituted imines as the key intermediates, which are generated from alkyl azides by Ru catalysis under photolytic conditions. Notably, this method avoids the use of a protective group strategy in the homopropargylic amine synthesis.

  提出了一种由烷基叠氮化物合成均丙炔胺的新方法。该反应的显着特征是涉及N-未取代的亚胺作为关键中间体，其是在光解条件下通过Ru催化由烷基叠氮化物生成的。值得注意的是，该方法避免了在炔丙基胺合成中使用保护基策略。
• Design, synthesis and biological evaluation of nonpeptide integrin antagonists
  作者：K.C. Nicolaou、John I. Trujillo、Bernd Jandeleit、Kelly Chibale、M. Rosenfeld、B. Diefenbach、D.A. Cheresh、S.L. Goodman

  DOI：10.1016/s0968-0896(98)00090-x

  日期：1998.8

  Recent studies demonstrated that peptide and antibody antagonists of integrin alpha(v)beta(3) block angiogenesis and tumor growth. In this article, the design, synthesis and biological evaluation of a series of nitroaryl ether-based, nonpeptide mimetics are described. The design of these compounds was based on Merck's arylether/alpha-aminoacid/guanidine framework and incorporates a novel nitroaryl system. The synthesized mimetics were tested against a variety of integrins (alpha(v)beta(3), alpha(IIb)beta(3), and alpha(v)beta(5)) in order to determine their binding selectivity and ability to inhibit cell adhesion. Selected compounds were also tested for their ability to inhibit angiogenesis in vivo in the CAM (chick chorioallantoic membrane) assay. From the generated compound library, compounds 16 and 19 proved to be potent and selective inhibitors of alpha(IIb)beta(3) (IC50 = 14 nM) whereas compound 11 showed excellent in vivo inhibition of angiogenesis (at 30 mu g/embryo). (C) 1998 Elsevier Science Ltd. All rights reserved.