ethyl N-trimethylsilylcarbamate | 998-86-7

• 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: ethyl N-trimethylsilylcarbamate
• 英文别名: N-trimethylsilylurethane；trimethylsilanyl-carbamic acid ethyl ester；Trimethylsilyl-carbamidsaeure-aethylester；N-trimethylsilyl-ethyl carbamate；trimethylsilyl ethyl carbamate；trimethylsilylurethane
• CAS: 998-86-7
• 化学式: C₆H₁₅NO₂Si
• 分子量: 161.276
• InChiKey: FSJQEJPDCPNWLC-UHFFFAOYSA-N

物化性质

• 沸点：
  170-175 °C
• 密度：
  0.9618 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  ethyl N-trimethylsilylcarbamate 、 bis(chloromethyl)phosphinic chloride 反应 1.0h， 以43%的产率得到bis(chloromethyl)phosphinic ethoxycarbonylamide
  参考文献：
  名称：

  Synthesis of 1,3,4-oxazaphospholines based on phosphorylated carbamates

  摘要：

  Addition of alcohols to bis(chloromethyl)phosphinoyl isocyanate, as well as the reaction of bis(chloromethyl)phosphinoyl chloride with urethanes or their silylated derivatives, gave the corresponding phosphorylated carbamates which undergo cyclization into 1,3,4-oxazaphospholines under the action of Et(3)N.

  DOI：

  10.1007/bf02496276
• 作为产物：
  描述：

  三甲基氯硅烷 、 氨基甲酸乙酯 在 三乙胺 作用下， 以 苯 为溶剂， 生成 ethyl N-trimethylsilylcarbamate
  参考文献：
  名称：

  Derkach,N.Ya.; Smetankina,N.P., Journal of general chemistry of the USSR, 1964, vol. 34, p. 3660 - 3662

  摘要：

  DOI：
• 作为试剂：
  描述：

  (RS)-N-(cyclohex-2-en-1-yl)benzamide 在 六甲基磷酰三胺 、 ethyl N-trimethylsilylcarbamate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 萘烷 为溶剂， 反应 158.75h， 生成 N-(cyclohex-2-enyl)-2-methyl-3-oxo-3-phenylpropanamide
  参考文献：
  名称：

  摘要：

  We report the synthesis of N-benzyl-N-[(E)-buta-1,3-dienyl]propanamide (6) and its corresponding O-silyl-subitituted ketene N,O-acetal 7 and their Diels-Alder reaction. Propanamide G reacted smoothly, whereas the yield obtained from 7 was low, probably due to polymerization of the dienophile induced by electron transfer. The ketene N,O-acetals 27a-g were synthesized starting from the corresponding benzamides 25a-e (Scheme 9). The ketene N,O-acetals 27a-g showed increased stabilities and underwent amino-Claisen rearrangements under thermal conditions. Using catalysts, interesting side reactions leading either to the annulated systems, rac-35-37 or to a beta -lactam rac-34 were observed.

  DOI：

  10.1002/1522-2675(20001004)83:10<2712::aid-hlca2712>3.0.co;2-d

文献信息

• Process for preparing 3'bromo-desacetoxycephalosporanic acid sulfoxide
  申请人：Gist-Brocades N.V.

  公开号：US04366315A1

  公开（公告）日：1982-12-28

  An improved process for the preparation of 3'-bromo-desacetoxycephalosphoranic acid sulfoxide compounds comprising protecting the 4-carboxy group of a 3'-unsubstituted cephalosporanic acid sulfoxide by silylating in an inert anhydrous organic solvent and brominating the silylated compound in situ which 3'-bromo compounds are valuable intermediates for the preparation of therapeutically useful cephalosporanic acid compounds.

  一种改进的制备3'-溴-去乙酰头霉素磺酰氧化物化合物的方法，包括通过在惰性无水有机溶剂中对3'-未取代头霉素磺酰氧化物的4-羧基进行硅化保护，并原位溴化硅化合物，从而制备具有药用价值的头霉素酸化合物的3'-溴化合物作为中间体。
• Lewis acid-catalyzed three-component condensation reactions of aldehydes, N-silylcarbamates, and allylsilane: synthesis of N-homoallylcarbamates
  作者：Lui Niimi、Ken-ichi Serita、Shuichi Hiraoka、Tsutomu Yokozawa

  DOI：10.1016/s0040-4039(00)01214-4

  日期：2000.9

  backbone and the allyl side chains, Lewis acid-catalyzed three-component condensation reactions of carbonyl compounds, N-trimethylsilylcarbamates, and allyltrimethylsilane are studied. The reaction of these three compounds took place in the presence of a catalytic amount of TrClO4 at 0°C to yield the corresponding N-homoallylcarbamates in good yields. This reaction was also applied to the synthesis of a

  为了同时构建聚氨酯主链和烯丙基侧链，研究了路易斯酸催化的羰基化合物，N-三甲基甲硅烷基氨基甲酸酯和烯丙基三甲基硅烷的三组分缩合反应。这三种化合物的反应在催化量的TrClO 4的存在下于0℃进行，以高收率得到相应的N-均烯丙基氨基甲酸酯。该反应还用于合成具有烯丙基侧链的聚氨酯。
• Silylation process
  申请人：Gist-Brocades N.V.

  公开号：US04400509A1

  公开（公告）日：1983-08-23

  An improved process for the trimethylsilylation of organic compounds with at least one active hydrogen atom with hexamethyldisilazane, the improvement comprising effecting the reaction in the presence of 0.001 to 10 mole percent of a catalyst of the formula X--NH--Y I wherein X and Y are individually an electron-withdrawing group or when X is an electron-withdrawing group, Y is selected from the group consisting of hydrogen and trialkylsilyl of 1 to 6 carbon atoms or X and Y together with the nitrogen atom to which they are attached form a cyclic electron-withdrawing group and novel trimethylsilylated thiols of the formula ##STR1## wherein R is a 5-or 6-membered heterocycle having at least one nitrogen or sulfur heteroatom and optionally substituted with at least one member of the group consisting of alkyl of 1 to 6 carbon atoms, phenyl, trimethylsilyl, trimethylsilyloxycarbonylmethyl and alkylamino of 1 to 6 carbon atoms, and novel trimethylsilylated 3'-substituted cephalosporanic acid derivatives.

  使用六甲基二硅氨基对至少含有一个活性氢原子的有机化合物进行三甲基硅基化的改进方法，其中改进包括在0.001到10摩尔％的催化剂存在下进行反应，所述催化剂的公式为X-NH-Y I，其中X和Y分别是电子吸引基团，或当X是电子吸引基团时，Y选自由1至6个碳原子的三烷基硅基或X和Y与它们附着的氮原子一起形成环状电子吸引基团；以及具有以下公式的新型三甲基硅基化硫醇：##STR1## 其中R是至少含有一个氮或硫杂原子的5或6成员杂环，并且可选择地被1至6个碳原子的烷基，苯基，三甲基硅基，三甲基硅氧羰基甲基和1至6个碳原子的烷基氨基中的一个成员取代，以及新型的三甲基硅基化3'-取代头孢菌素酸衍生物。
• Process for the preparation of cephalosporin compounds
  申请人：Glaxo Group Limited

  公开号：US04258183A1

  公开（公告）日：1981-03-24

  A process for the preparation of a 3-carbamoyloxymethyl cephalosporin compound which comprises hydrolyzing a 3-phosphonocarbamoyloxymethyl cephalosporin compound. The hydrolysis is preferably effected at a pH in the range of pH3 to 4, for example using aqueous sodium hydrogen carbonate.

  一种制备3-氨甲氧基甲基头孢菌素化合物的方法，包括水解3-磷酸氨甲氧基甲基头孢菌素化合物。最好在pH3至4范围内进行水解，例如使用水合碳酸氢钠。
• Beiträge zur Chemie der Silicium—Stickstoff-Verbindungen, 16. Mitt.: N-Silyl-carbonamide und N-Silyl-carbamidsäureester
  作者：Joachim Pump、Ulrich Wannagat

  DOI：10.1007/bf00903131

  日期：1962.3