N,O-bis(trimethylsilyl) acetamide | 73846-26-1

• 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: N,O-bis(trimethylsilyl) acetamide
• 英文别名: N-trimethylsilyl-1-trimethylsilyloxyvinylamine；N-trimethylsilyl-1-trimethylsilyloxyethenamine
• CAS: 73846-26-1
• 化学式: C₈H₂₁NOSi₂
• 分子量: 203.432
• InChiKey: VXYIGUTZCMWPBV-UHFFFAOYSA-N

物化性质

• 沸点：
  182.3±32.0 °C(Predicted)
• 密度：
  0.840±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氟胞嘧啶 、 N,O-bis(trimethylsilyl) acetamide 反应 1.0h， 生成 2-trimethylsilyloxy-4-trimethylsilylamino-5-fluoropyrimidine
  参考文献：
  名称：

  The synthesis of novel 3′,5′-homocyclic nucleotides as potential anti-HIV agents

  摘要：

  (5S)-(5-叔丁基二甲基硅氧基甲基)呋喃-2(5H)-酮已被转化为胞苷2′,3′-二脱氧-3′,5′-同环单磷酸（及其5-氟同系物）和腺苷同环单磷酸。这些分子被设计为HIV逆转录酶的抑制剂，尽管它们并不具备此种活性。

  DOI：

  10.1039/a900800d
• 作为产物：
  描述：

  N-三甲基硅基乙酰胺 、 N-(trimethylsilyl)-2-methylimidazole 生成 N,O-bis(trimethylsilyl) acetamide
  参考文献：
  名称：

  SINOXARA, NORIO;KOGIVA, MASAXIKO

  摘要：

  DOI：
• 作为试剂：
  描述：

  (3R,4R,5S)-tert-butyl 2-acetoxy-3,4,5-tris(benzyloxy)-piperidine-1-carboxylate 、 胸腺嘧啶 在 N,O-bis(trimethylsilyl) acetamide 、 三氟甲磺酸三甲基硅酯 、 碳酸氢钠 作用下， 以 乙腈 、 水 为溶剂， 反应 3.25h， 以35%的产率得到(2S,3S,4R,5S)-tert-butyl 3,4,5-tris(benzyloxy)-2-(thymin-1-yl)piperidine-1-carboxylate
  参考文献：
  名称：

  六元氮杂核苷类似物的合成及其体外抗乙型肝炎病毒活性

  摘要：

  制备了十五种新颖的六元氮杂核苷衍生物，并对其在人肝母细胞瘤衍生的肝Hep-G2细胞中的抗乙型肝炎病毒（HBV）活性和细胞毒性进行了评估。最强效的化合物16b，IC 50公开了2.74μg/ mL的值（低于3TC）和13.5的SI值。关键的合成步骤涉及内酯的重排（很容易从单糖中获得）和路易斯酸催化的碱基与氮杂糖供体的缩合。使用通用的乙酰化氮杂糖供体，成功获得了覆盖三种类型的氮杂糖和四种类型的天然核碱基的氮杂核苷。实验结果表明，某些六元氮杂核苷可能会在发现新的抗病毒药物中找到应用。

  DOI：

  10.1016/j.bmc.2010.11.063

文献信息

• <i>N</i>-Trimethylsilyl Amines for Controlled Ring-Opening Polymerization of Amino Acid <i>N</i>-Carboxyanhydrides and Facile End Group Functionalization of Polypeptides
  作者：Hua Lu、Jianjun Cheng

  DOI：10.1021/ja803304x

  日期：2008.9.24

  N-trimethylsilyl (N-TMS) amine to mediate controlled ring-opening polymerization of amino acid N-carboxyanhydrides (NCAs). This polymerization proceeds via a unique, trimethylsilyl carbamate (TMS-CBM) propagating group that results from the cleavage of the Si-N bond of N-TMS amine followed by NCA ring opening. Propagation of the polypeptide chains proceeds through the transfer of the TMS group from the terminal

  我们报告了一种新策略，该策略使用 N-三甲基甲硅烷基 (N-TMS) 胺来介导氨基酸 N-羧酸酐 (NCA) 的受控开环聚合。该聚合通过独特的氨基甲酸三甲基甲硅烷基酯 (TMS-CBM) 增长基团进行，该增长基团由 N-TMS 胺的 Si-N 键断裂随后 NCA 开环产生。多肽链的传播通过将 TMS 基团从末端 TMS-CBM 转移到进入的单体进行，然后形成新的 TMS-CBM 传播基团。TMS-CBM 的形成由 MS 和 NMR 证实。通过 N-TMS 胺介导的聚合形成的多肽具有预期的分子量、窄的分子量分布和多肽 C 末端的受控官能团。
• Novel Stereoselective Entry to 2‘-β-Carbon-Substituted 2‘-Deoxy-4‘-thionucleosides from 4-Thiofuranoid Glycals
  作者：Kazuhiro Haraguchi、Noriaki Shiina、Yuichi Yoshimura、Hisashi Shimada、Kyoko Hashimoto、Hiromichi Tanaka

  DOI：10.1021/ol040035u

  日期：2004.8.1

  2'-deoxy-4'-thionucleosides have been synthesized through PhSeCl-mediated electrophilic glycosidation using 4-thiofuranoid glycals having carbon substituents at the C2-position as a glycosyl donor. Preparation of these glycals were carried out by means of the C2 lithiation of 1-chloro-4-thiofuranoid glycal with LTMP followed by the Birch reduction of the chlorine atom. [reaction: see text]

  已通过PhSeCl介导的亲电糖基化反应合成了2'-β-甲基-和2'-β-羟甲基-2'-脱氧-4'-硫代核苷，使用在C2-位具有碳取代基的4-硫代呋喃类糖作为糖基供体。这些糖的制备是通过用LTMP对1-氯-4-硫代呋喃呋喃基糖进行C2锂化反应，然后将Birch还原成氯原子来进行的。[反应：看文字]
• Synthesis and chemoselective activation of phenyl 3,5-di-O-benzyl-2-O,4-C-methylene-1-thio-β-d-ribofuranoside: a key synthon towards α-LNA
  作者：Poul Nielsen、Jesper Wengel

  DOI：10.1039/a806817h

  日期：——

  A bicyclic thiofuranoside (phenyl 3,5-di-O-benzyl-2-O,4-C-methylene-β-D-ribofuranoside) was efficiently synthesized and introduced as the key synthon in a method for convergent synthesis of α- and β-LNA nucleosides; acid-induced ring-opening reactions of the corresponding bicyclic methyl furanoside are also described.

  一种双环硫呋喃苷（苯基3,5-二-O-苄基-2-O,4-C-亚甲基-β-D-核糖呋喃苷）被高效合成并作为α-和β-LNA核苷的聚合合成中的关键合成物引入；还描述了相应双环甲基呋喃苷的酸诱导开环反应。
• Synthesis of carminic acid, the colourant principle of cochineal
  作者：Pietro Allevi、Mario Anastasia、Steve Bingham、Pierangela Ciuffreda、Alberto Fiecchi、Giuliana Cighetti、Max Muir、Antonio Scala、John Tyman

  DOI：10.1039/a705145j

  日期：——

  The first synthesis of carminic acid (7β-D-glucopyranosyl-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid) is described. Selective C-glycosylation at the 7-position of ethyl and benzyl 3,5,8,9,10-pentamethoxy-1-methylanthracene-2-carboxylates with 2,3,4,6-tetra-O-benzyl-1-trifluoroacetyl-α-D-glucopyranose afforded intermediates which were oxidised to ethyl and benzyl 3,5,8-trimethoxy-1-methyl-9,10-dioxo-7-(2′,3′,4′,6′-tetra-O-benzyl-β-D-glucopyranosyl)-9,10-dihydroanthracene-2-carboxylate respectively. The benzyl compound was hydrogenolysed and the ethyl analogue hydrogenolysed and hydrolysed to give the same product, which was tetraacetylated and demethylated to afford 6-deoxycarminic acid tetraacetate, 3,5,8-trihydroxy-1-methyl-9,10-dioxo-7-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)-9,10-dihydroanthracene-2-carboxylic acid. The pentamethoxy intermediates were obtained from 2-chloronaphthazarin by Diels–Alder addition to 3-alkoxycarbonyl-2,4-bis(trimethylsiloxy)penta-2,4-dienes to give alkyl 6-deoxykermesates. Methylation afforded the corresponding trimethyl ethers, which by reductive methylation gave the required pentamethoxy compounds. By known steps 6-deoxycarminic acid tetraacetate was converted into the 5,8,9,10-bisquinone, acetoxylation of which gave carminic acid octaacetate. Acidic hydrolysis afforded carminic acid.

  首次合成了胭脂酸（7β-D-葡萄糖吡喃糖基-3,5,6,8-四羟基-1-甲基-9,10-二氧基-9,10-二氢蒽-2-羧酸）。选择性地在乙基和苄基3,5,8,9,10-五甲氧基-1-甲基蒽-2-羧酸酯的7位进行C-糖苷化，与2,3,4,6-四-O-苄基-1-三氟乙酰-α-D-葡萄糖吡喃糖反应得到了中间体，随后氧化得到乙基和苄基3,5,8-三甲氧基-1-甲基-9,10-二氧基-7-(2′,3′,4′,6′-四-O-苄基-β-D-葡萄糖吡喃糖)-9,10-二氢蒽-2-羧酸酯。苄基化合物经过氢解，乙基类似物经过氢解和水解，得到了相同的产物，然后进行四乙酰化和脱甲基反应，得到6-脱氧胭脂酸四乙酸酯，即3,5,8-三羟基-1-甲基-9,10-二氧基-7-(2′,3′,4′,6′-四-O-乙酰-β-D-葡萄糖吡喃糖)-9,10-二氢蒽-2-羧酸。五甲氧基中间体是通过将2-氯萘扎林与3-烷氧基羧基-2,4-双(trimethylsiloxy)戊-2,4-二烯进行Diels-Alder反应获得的，以得到烷基6-脱氧克尔梅酸酯。甲基化反应产生相应的三甲基醚，经过还原甲基化得到所需的五甲氧基化合物。通过已知步骤，6-脱氧胭脂酸四乙酸酯被转化为5,8,9,10-双醌，进一步的醋酸化反应得到胭脂酸八乙酸酯。酸性水解反应得到胭脂酸。
• Preparation of functtonalised anthra[b]cyclobutenes from 3,6-dimethoxybenzocyclobutenone
  作者：Manouchehr Azadi-Ardakani、Roy Hayes、Timothy W. Wallace

  DOI：10.1016/s0040-4020(01)87872-8

  日期：1990.1

  ne-l,4,9-trione 9, a potential anthracycline precursor, has been prepared from 3,6-dimethoxybenzocyclobutenone 4 via quinone acetal and phthalide anion chemistry. Dials-Alder and electrophilic phthaloylation approaches to 9 were unsuccessful.

  3,10-二甲氧基氯丁[b]蒽-1,4,9-三酮9，一种潜在的蒽环类前体，是由3,6-二甲氧基苯并环丁烯酮4经醌缩醛和邻苯二甲酸酯阴离子化学反应制得的。Dials-Alder和亲电邻苯二甲酰化方法均未成功达到9。