N,O-bis(trimethylsilyl)acetamide | 32605-52-0

• 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,O-bistrimethylsilylacetamide；bis(trimethylsilyl)acetamide；bis-TMS-acetamide；BSA；N,O-bis(trimethylsilyl)-acetamide；N,O-bis-(trimethylsilyl)acetamide；N-trimethylsilyl-1-trimethylsilyloxyethanamine
• CAS: 32605-52-0
• 化学式: C₈H₂₃NOSi₂
• 分子量: 205.448
• InChiKey: GKCGZFRGMYQQBX-UHFFFAOYSA-N

物化性质

• 沸点：
  165.4±23.0 °C(Predicted)
• 密度：
  0.829±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  N,O-bis(trimethylsilyl)acetamide 在 溴(二氟)膦 作用下， 反应 0.5h， 生成 三甲基溴硅烷 、 trimethylsilylN-(difluorophosphanyl)acetimidate
  参考文献：
  名称：

  含二氟膦基的乙酰胺衍生物

  摘要：

  双（三甲基甲硅烷基）乙酰胺在–80°C下与等摩尔比例的PF 2 Br反应，得到CH 3 C（OSiMe 3）：NPF 2。PF 2 Br过量时，–80°C的初始产物为CH 3 C（OPF 2）：NPF 2；在高于–40°C的温度下，会缓慢重新排列，以生成CH 3 C（OPF 2）：NPF 2和CH 3 CON（PF 2）2的混合物。乙酰胺的所有这些PF 2衍生物在室温下缓慢分解，生成乙腈和任一PF 2 OSiMe 3或（PF 2）2 O.它们的特点是1 H，19 F和31 P NMR和通过IR光谱。没有证据表明N和O位之间可以快速交换PF 2基团。

  DOI：

  10.1039/dt9800001768
• 作为试剂：
  描述：

  1,3-二苯基-2-丙烯基乙酸酯 、 乙酰丙酮 在 bis(η3-allyl-μ-chloropalladium(II)) 、 (2R,3R)-1,1-bis[(diphenylphosphanyl)methyl]-2,3-diphenylcyclopropane 、 potassium acetate 、 N,O-bis(trimethylsilyl)acetamide 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (S)-3-(1',3'-di(phenyl)prop-2'-enyl)pentane-2,4-dione 、 (R)-3-(1',3'-di(phenyl)prop-2'-enyl)pentane-2,4-dione
  参考文献：
  名称：

  trans-(2R,3R)-2,3-Diphenylcyclopropane-1,1-dimethanol: a pivotal diol for the synthesis of novel C2-symmetric ligands for asymmetric transition metal catalysis

  摘要：

  Various chiral ligands bearing phosphorus or nitrogen donor atoms were obtained in a straightforward manner starting from trans-(2R,3R)-diphenylcyclopropane-1,1-dimethanol as a key structure. These chiral ligands were tested and compared in palladium(0)-catalyzed asymmetric allylic alkylation reactions (up to 71% ee) and rhodium(1)-catalyzed asymmetric hydrogenations (up to 88% ee). Moreover, in the asymmetric allylic alkylation, we observed excellent activity with a diphosphinite ligand (TOF = 600 mol 17 x [mol Pd x h)(-1)]. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.08.007

文献信息

• Addition of functionalized organolithium reagents to p-benzoquinones and cyclohexadienones: synthesis of functionalized cyclohexadienones, dienols and dienediols
  作者：Alfred Fischer、George Narayanan Henderson

  DOI：10.1016/s0040-4039(00)81347-7

  日期：1983.1

  Low temperature addition of functionalized alkyllithium reagents to p-benzoquinones produces 4-alkyl-4-hydroxycyclohexa-2,5-dienones, and reaction of excess of the reagents with quinones yields 1,4-dialkylcyclohexa-2,5-diene-1,4-diols. With 4-acetoxy-, 4-hydroxy-, and 4-methoxy-4-methylcyclohexa-2,5-dienones the corresponding dienols are obtained. A one-step synthesis of the antibiotics 4-acetamido-

  在对苯醌中低温添加官能化的烷基锂试剂会生成4-烷基-4-羟基环己2,5-二烯酮，过量的试剂与醌反应会生成1,4-二烷基环己-2,5-二烯-1， 4-二醇。用4-乙酰氧基-，4-羟基-和4-甲氧基-4-甲基环己-2,5-二烯酮得到相应的二烯醇。描述了抗生素4-乙酰氨基-和4-[（（乙氧基羰基）甲基] -2,6-二溴-4-羟基环己二酮和抗肿瘤剂jacaranone的一步合成。
• C-8 HALOGENATED MACROLIDES
  申请人：KIM IN JONG

  公开号：US20090209547A1

  公开（公告）日：2009-08-20

  The present invention discloses compounds of formula (I) or pharmaceutically acceptable salts, esters, or prodrugs thereof: which exhibit antibacterial properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of antibiotic treatment. The invention also relates to methods of treating a bacterial infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The invention further includes process by which to make the compounds of the present invention.

  本发明公开了具有以下结构的化合物（I）或其药用可接受的盐、酯或前药：该化合物具有抗菌性能。本发明还涉及包括上述化合物的药物组合物，用于治疗需要抗生素治疗的受试者。该发明还涉及通过给予包含本发明化合物的药物组合物来治疗受试者的细菌感染的方法。该发明还包括制备本发明化合物的方法。
• Asymmetric aldol reaction of α-ketoesters with isocyanoacetate and isocyanoacetamide catalyzed by a chiral ferrocenylphosphine-gold(I) complex
  作者：Yoshihiko Ito、Masaya Sawamura、Hitoshi Hamashima、Takashi Emura、Tamio Hayashi

  DOI：10.1016/s0040-4039(01)80773-5

  日期：1989.1

  Asymmetric aldol reaction of α-ketoesters (RCOCOOMe: R = Me, i-Bu, Ph) with methyl isocyanoacetate or N, N-dimethyl-α-isocyanoacetamide in the presence of 1 mol% of a chiral (aminoalkyl) ferrocenylphosphine-gold(I) catalyst proceeded with high enantioselectivity to give corresponding oxazolines of up to 90% ee, which were converted into optically active β-alkyl-β-hydroxyaspartic acid derivatives.

  α-酮酸酯（RCOCOOMe：R = Me，i- Bu，Ph）与异氰基乙酸甲酯或N，N-二甲基-α-异氰基乙酰胺在1 mol％手性（氨基烷基）二茂铁基膦-金（ I）催化剂以高对映选择性进行，得到至多90％ee的相应的恶唑啉，将其转化为旋光的β-烷基-β-羟基天冬氨酸衍生物。
• Formation route of sulfur-containing metabolites of afloqualone, a new centrally acting muscle relaxant, in rat.
  作者：MINEZO OTSUKA、SATOSHI FURUUCHI、SHOICHI HARIGAYA

  DOI：10.1248/cpb.31.2799

  日期：——

  The formation route of the sulfur-containing metabolites of afloqualone [6-amino-2-fluoromethyl-3-(o-tolyl)-4(3H)-quinazolinone, AFQ], a centrally acting muscle relaxant, was studied in rats. When 14C-N-acetyl AFQ 2-mercapturate (AFQM) methyl ester was administered orally to normal rats, it was excreted in the bile as AFQM, one of the major biliary metabolites of AFQ, and in the urine as sulfur-containing metabolites of AFQ such as methylsulfinyl and methylsulfonyl metabolites of AFQ. This indicated that AFQM was a precursor of these methylsulfinyl and -sulfonyl metabolites. Pretreatment of rats with antibiotics significantly reduced the urinary excretion of 14C-AFQM and its metabolites as compared with normal rats. Oral administration of 14C-AFQ to antibiotics-treated rats also significantly reduced the amounts of the sulfur-containing metabolites excreted into the urine, but did not affect the amounts of other non-sulfur-containing metabolites. In addition, oral administration of 14C-AFQ to bile-duct-ligated rats gave results similar to those in the antibiotics-treated rats. These results indicate that in normal rats microfloral metabolism is necessary for the formation of the methylsulfinyl and -sulfonyl metabolites from AFQM and other unidentified mercapturate pathway conjugates excreted into the bile. The metabolites of AFQ produced by the microflora are reabsorbed into the systemic circulation, processed by further metabolism in the liver, and in turn excreted in the urine.

  本研究以大鼠为研究对象，研究了一种中枢作用的肌肉松弛剂阿夫喹酮[6-氨基-2-氟甲基-3-（邻甲苯基）-4(3H)-喹唑啉酮，AFQ]的含硫代谢物的形成途径。给正常大鼠口服 14C-N-acetyl AFQ 2-巯基（AFQM）甲酯后，其在胆汁中以 AFQM（AFQ 的主要胆汁代谢物之一）的形式排泄，在尿液中则以 AFQ 的含硫代谢物（如 AFQ 的甲亚磺酰和甲亚磺酰代谢物）的形式排泄。这表明 AFQM 是这些甲基亚磺酰和-亚磺酰代谢物的前体。与正常大鼠相比，用抗生素对大鼠进行预处理可明显减少 14C-AFQM 及其代谢物在尿液中的排泄。经抗生素处理的大鼠口服 14C-AFQ 后，排入尿液的含硫代谢物数量也会明显减少，但不会影响其他非含硫代谢物的数量。此外，胆管结扎大鼠口服 14C-AFQ 的结果与抗生素治疗大鼠的结果相似。这些结果表明，在正常大鼠体内，从 AFQM 和其他排泄到胆汁中的不明巯基途径共轭物中形成甲基亚磺酰和-亚磺酰代谢物需要微花代谢。微生物群产生的 AFQ 代谢物会被重吸收进入体循环，在肝脏中进一步代谢处理，然后随尿液排出体外。
• [DE] CHIRALE LIGANDEN UND DEREN ÜBERGANGSMETALLKOMPLEXE<br/>[EN] CHIRAL LIGANDS AND THEIR TRANSITION METAL COMPLEXES<br/>[FR] LIGANDS CHIRAUX ET LEURS COMPLEXES DE METAUX DE TRANSITION
  申请人：BAYER CHEMICALS AG

  公开号：WO2004104014A3

  公开（公告）日：2005-03-17