(2-bromoethoxy)triethylsilane

• 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
• 英文名称: (2-bromoethoxy)triethylsilane
• 英文别名: 2-bromoethoxy(triethyl)silane
• 化学式: C₈H₁₉BrOSi
• 分子量: 239.228
• InChiKey: ASNKMCWTDURAGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-bromoethoxy)triethylsilane 在 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,2-Dimethyl-4-triethylsilanyloxy-butan-1-ol
  参考文献：
  名称：

  富含电子的芳香亲核试剂通过Rh（II）催化N-磺酰基-1,2,3-三唑的环转移反应合成6位取代的哌啶-3-酮

  摘要：

  首次报道了高度非对映选择性的铑（II）催化的醛基化N-磺酰基三唑与富电子芳族亲核试剂的转环反应，提供了功能化的6-取代的哌啶-3-酮。该反应具有广泛的底物范围，包括脂族和芳族N-磺酰基-1,2,3-三唑以及各种芳族亲核试剂。已证明添加催化量的路易斯酸对于提高产率至关重要。通过采用这种方法，可以获得带有季碳的几乎不易获得的哌啶-3-酮。

  DOI：

  10.1021/acs.orglett.7b01180
• 作为产物：
  描述：

  三乙基硅基三氟甲磺酸酯 、 2-溴乙醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以85%的产率得到(2-bromoethoxy)triethylsilane
  参考文献：
  名称：

  富含电子的芳香亲核试剂通过Rh（II）催化N-磺酰基-1,2,3-三唑的环转移反应合成6位取代的哌啶-3-酮

  摘要：

  首次报道了高度非对映选择性的铑（II）催化的醛基化N-磺酰基三唑与富电子芳族亲核试剂的转环反应，提供了功能化的6-取代的哌啶-3-酮。该反应具有广泛的底物范围，包括脂族和芳族N-磺酰基-1,2,3-三唑以及各种芳族亲核试剂。已证明添加催化量的路易斯酸对于提高产率至关重要。通过采用这种方法，可以获得带有季碳的几乎不易获得的哌啶-3-酮。

  DOI：

  10.1021/acs.orglett.7b01180

文献信息

• Stereoselective Formal Synthesis of (+)-Allokainic Acid <i>via</i> Thiol-Mediated Acyl Radical Cyclization
  作者：Ken-ichi Yamada、Tomohiro Sato、Masaki Hosoi、Yasutomo Yamamoto、Kiyoshi Tomioka

  DOI：10.1248/cpb.58.1511

  日期：——

  Stereoselective formal synthesis of (+)-allokainic acid was accomplished starting from L-glutamate by using a thiol-mediated acyl radical cyclization as a key step. The cyclization of a formylalkenoate proceeded in a highly diastereoselective manner to give trans-4,5-disubstituted pyrrolidin-3-one without the production of the cis-isomer. The pyrrolidinone was then converted into the established synthetic

  通过使用巯基介导的酰基自由基环化作为关键步骤，从L-谷氨酸开始完成（+）-alkakainic酸的立体选择性形式合成。甲酰基链烯酸酯的环化以高度非对映选择性的方式进行，得到反式-4,5-二取代的吡咯烷-3--3-酮，而没有产生顺式异构体。然后，通过与异丙烯基格利雅试剂的铁催化的偶联反应，将吡咯烷酮转化为已建立的（+）-链烷酸的合成中间体。
• S-3578, A New Broad Spectrum Parenteral Cephalosporin Exhibiting Potent Activity Against both Methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa Synthesis and Structure-activity Relationships.
  作者：HIDENORI YOSHIZAWA、HIKARU ITANI、KOJI ISHIKURA、TADASHI IRIE、KATSUKI YOKOO、TADATOSHI KUBOTA、KYOJI MINAMI、TSUTOMU IWAKI、HIDEAKI MIWA、YASUHIRO NISHITANI

  DOI：10.7164/antibiotics.55.975

  日期：——

  A series of 7-aminothiadiazolylcephalosporins having a 1-(substituted)-1H-imidazo[4, 5-b]pyridinium group at the C-3' position of the cephem nucleus were synthesized and evaluated for in vitro antibacterial activities. Among the cephalosporins prepared in this study, 7β-[2-(5-amino-1, 2, 4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacetamido]-3-[1-(3-methylaminopropyl)-1H-imidazo[4, 5-b]pyridinium-4-yl]methyl-3-cephem-4-carboxylate sulfate (S-3578) showed extremely potent broad spectrum activity against both Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA) and Gram-negative bacteria including Pseudomonas aeruginosa, and good water solubility.

  一系列具有1-(取代基)-1H-咪唑[4, 5-b]吡啶铵基团的7-氨基噻二唑基头孢菌素在头孢核的C-3'位点合成并评估其体外抗菌活性。在本研究中制备的头孢菌素中，7β-[2-(5-amino-1, 2, 4-thiadiazol-3-yl)-2(Z)-ethoxyiminoacetamido]-3-[1-(3-methylaminopropyl)-1H-imidazo[4, 5-b]pyridinium-4-yl]methyl-3-头孢-4-羧酸盐硫酸盐(S-3578)对革兰氏阳性细菌（包括抗甲氧西林的金黄色葡萄球菌MRSA）和革兰氏阴性细菌（包括铜绿色假单胞菌）表现出极强的广谱活性，并且具有良好的水溶性。
• Highly Electrophilic Mononuclear Cationic Aluminium Alkoxide Complexes: Syntheses, Reactivity and Catalytic Applications
  作者：Mamta Bhandari、Mandeep Kaur、Sandeep Rawat、Sanjay Singh

  DOI：10.1002/chem.202301229

  日期：2023.10.2

  New cationic aluminium complexes with terminal alkoxy substituents (−OMe and −OtBu) are reported; these showed markedly higher Lewis acidity than the known hydride and methyl analogues, as evident from their Gutmann-Beckett test, NBO analysis and hydride ion affinity calculations. These complexes activate triethylsilane and are good catalysts for the hydrosilylation of ethers, carbonyls, and alkene

  报道了带有末端烷氧基取代基（-OMe 和 -O t Bu）的新型阳离子铝配合物；从 Gutmann-Beckett 测试、NBO 分析和氢负离子亲和力计算中可以看出，这些化合物的路易斯酸度明显高于已知的氢化物和甲基类似物。这些配合物可活化三乙基硅烷，是醚、羰基化合物和烯烃氢化硅烷化的良好催化剂。
• New broad-spectrum parenteral cephalosporins exhibiting potent activity against both methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa. Part 2: Synthesis and structure–activity relationships in the S-3578 series
  作者：Hidenori Yoshizawa、Tadatoshi Kubota、Hikaru Itani、Hiroyuki Ishitobi、Hideaki Miwa、Yasuhiro Nishitani

  DOI：10.1016/j.bmc.2004.05.022

  日期：2004.8.1

  Among the prepared novel cephalosporin derivatives related to S-3578, a series of 7beta-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z) -ethoxyiminoacetamido]-3-[1-(aminoalkyl)-1H-pyrazoIo[4,3-b]pyridinium-4-yl]methyl-3-cephem-4-carboxylate showed potent activity against both MRSA and Pseudomonas aeruginosa, and displayed good water solubility. (C) 2004 Elsevier Ltd. All rights reserved.
• A novel series of parenteral cephalosporins exhibiting potent activities against both Pseudomonas aeruginosa and other Gram-negative pathogens. Part 2: Synthesis and structure–activity relationships
  作者：Kenji Yamawaki、Takashi Nomura、Tatsuro Yasukata、Norihiko Tanimoto、Koichi Uotani、Hideaki Miwa、Yoshinori Yamano、Kei Takeda、Yasuhiro Nishitani

  DOI：10.1016/j.bmc.2007.11.028

  日期：2008.2.15

  A novel series of 7 beta-[2-(2-amino-5-chloro-thiazol-4-yl)-2(Z)-((S)-1-carboxyethoxyimino)acetamido]cephalosporins bearing various pyridinium groups at the C-3' position were synthesized and their in vitro antibacterial activities against Gram-negative pathogens including Pseudomonas aeruginosa and several Gram-positive pathogens were evaluated. Among the cephalosporins prepared, we found that a cephalosporin bearing the 2- amino-1-(3-methylamino-propyl)-1H-imidazo[4,5-b] pyridinium group at the C-3' position (8a) showed potent and well-balanced antibacterial activities against P. aeruginosa and other Gram-negative pathogens including the strains which produce class C beta-lactamase and extended spectrum beta-lactamase (ESBL). Compound 8a also showed efficacious in vivo activity and high stability against AmpC beta-lactamase. These findings indicate that 2-aminoimidazopyridinium having an aminoalkyl group at the 1-position as a C-3' side chain is suitable for cephalosporins bearing an aminochlorothiazolyl moiety and a carboxyethoxyimino moiety on the C-7 side chain. (C) 2007 Elsevier Ltd. All rights reserved.