2-((叔丁基二苯基甲硅烷基)氧基)-N-甲氧基-N-甲基乙酰胺 | 154698-93-8

• 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-((叔丁基二苯基甲硅烷基)氧基)-N-甲氧基-N-甲基乙酰胺
• 英文名称: 2-((tert-butyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide
• 英文别名: 2-[tert-butyl(diphenyl)silyl]oxy-N-methoxy-N-methylacetamide
• CAS: 154698-93-8
• 化学式: C₂₀H₂₇NO₃Si
• 分子量: 357.525
• InChiKey: ODVRWJKLOZNLAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  395.0±48.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存放在室温下，并保持干燥和密封。

反应信息

• 作为反应物：
  描述：

  2-((叔丁基二苯基甲硅烷基)氧基)-N-甲氧基-N-甲基乙酰胺 在 {[(1S,2S)-TsDPEN]RuCl(η⁶-p-cymene)} 正丁基锂 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 1.83h， 生成 (2S)-1-[tert-butyl(diphenyl)silyl]oxy-6-[(4-methoxyphenyl)methoxy]-5,5-dimethylhex-3-yn-2-ol
  参考文献：
  名称：

  A Formal Synthesis of Psymberin

  摘要：

  A formal synthesis of psymberin (irciniastatin A) is presented. Notable features of the synthesis include the chemo-, regio-, and stereoselective oxidation of a 1,3-disubstituted allene, a configuration-dependent spirodiepoxide opening, the efficient syntheses of functionalized trans-2,6-disubstituted pyrans, and the union of a highly functionalized aldehyde with a pentasubstituted aryl homoenolate to give a dihydroisocumarin.

  DOI：

  10.1021/ol063143k
• 作为产物：
  描述：

  2-((叔丁基二苯基甲硅烷基)氧基)乙酸甲酯 在 水 、 N,N'-二环己基碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-((叔丁基二苯基甲硅烷基)氧基)-N-甲氧基-N-甲基乙酰胺
  参考文献：
  名称：

  An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing

  摘要：

  Autoinducer-2 (AI-2) is a signalling molecule for bacterial inter-species communication. A synthesis of (S)-4,5-dihydroxypentane-2,3-dione (DPD), the precursor of AI-2, is described starting from methyl glycolate. The key step was an asymmetric reduction of a ketone with (S)-Alpine borane. This new method was highly reproducible affording DPD for biological tests without contaminants. The biological activity was tested with the previously available assays and compared with a new method using an Escherichia coli reporter strain thus avoiding the use of the pathogenic Salmonella reporter. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.036

文献信息

• Lewis Acid Catalyzed Intramolecular Diels−Alder Reactions of Acyclic (<i>Z</i>)-Substituted 1,3-Dienes
  作者：Neal A. Yakelis、William R. Roush

  DOI：10.1021/ol015667k

  日期：2001.3.1

  Lewis acid catalyzed intramolecular Diels-Alder reactions of trienes (E,E,Z)-1a-d, (E,E,Z)-4a-d, and (E,Z,Z)-7a,b are described. Trienes containing enal or enone dienophiles cyclize in excellent yield under mild conditions using substoichiometric amounts of MeAlCl(2), in most cases with high levels of diastereoselectivity. The thermal IMDA reactions of 1a, 4a, and 7a require forcing conditions and

  描述了路易斯酸催化的三烯（E，E，Z）-1a-d，（E，E，Z）-4a-d和（E，Z，Z）-7a，b的分子内Diels-Alder反应。在大多数情况下，非对映选择性很高的情况下，使用亚化学计量的MeAlCl（2），在温和的条件下，含有烯或烯双烯亲二烯的三烯以优异的产率环化。1a，4a和7a的IMDA热反应需要强制条件，在1a和4a的情况下，产率低且立体选择性相反。
• Studies on the synthesis of the quartromicins: partial stereochemical assignment of quartromicins A3 and D3 and diastereoselective synthesis of the endo- and exo-spirotetronate subunits
  作者：William R Roush、David A Barda、Chris Limberakis、Roxanne K Kunz

  DOI：10.1016/s0040-4020(02)00656-7

  日期：2002.8

  A partial stereochemical assignment of quartromicins A3 and D3 is presented, along with diastereoselective syntheses of the endo- and exo-spirotetronates 1 and 2, corresponding to the galacto and agalacto fragments of the proposed quartromicin stereostructure. The key steps of these syntheses are highly enantio- and diastereoselective Lewis acid catalyzed Diels–Alder reactions of 1,1,3,4-tetrasubstituted

  quartromicins A的局部立体化学指定3和d 3被呈现，用非对映选择性合成沿着内切-和外切-spirotetronates 1和2中，对应于半乳糖和agalacto拟议quartromicin立体的片段。这些合成的关键步骤是高度对映体和非对映体选择性路易斯酸催化1,1,3,4-四取代的二烯24的Diels-Alder反应。
• Highly Enantiopure (<i>tert</i>-Butyldiphenylsilyloxymethyl)Oxiranes from Barium Carbonate
  作者：I. VictorEkhato、Mark Palazzolo

  DOI：10.1080/00397919808004924

  日期：1998.10

  (2R)-(tert-butyldiphenylsilyloxymethyl)oxirane and the (2S)-enantiomer from barium carbonate was developed. Methyl glycolate or the hydroxamate analog was prepared and in turn reacted with (S)-(-)-methyl p-tolylsulfoxide or the (R)-enantiomer to make β-keto sulfoxides. From the sulfoxides, we made the diastereoisomeric alcohols in a highly selective sulfoxide group directed hydride reduction, and a Pummerer

  摘要 开发了以碳酸钡为原料合成(2R)-(叔丁基二苯基甲硅烷氧基甲基)环氧乙烷和(2S)-对映异构体的方法。制备乙醇酸甲酯或异羟肟酸酯类似物，然后与 (S)-(-)-甲基对甲苯基亚砜或 (R)-对映异构体反应以制备 β-酮亚砜。从亚砜中，我们在高度选择性的亚砜基团导向的氢化物还原中制备了非对映异构醇，然后进行普默勒重排反应，然后脱保护产生对映体二醇。(2R)-(叔丁基二苯基甲硅烷氧基甲基)环氧乙烷和它的(2S)-对映异构体以56%的总产率从碳酸钡衍生自这些二醇。开发此方法是为了方便获取这些化合物的同位素标记类似物。
• The Preparation and Utility of Bis(sulfinyl)imidoamidine Ligands for the Copper-Catalyzed Diels−Alder Reaction
  作者：Timothy D. Owens、Andrew J. Souers、Jonathan A. Ellman

  DOI：10.1021/jo020524c

  日期：2003.1.1

  The design and preparation of a novel class of ligands based on the sulfinyl imine functionality is described. In particular, an efficient and modular synthesis of bis(sulfinyl)imidoamidine (siam) ligands is reported. The versatility of the synthetic sequence is demonstrated by the preparation of various analogues to explore the effect of substitution about the ligand framework on catalytic activity

  描述了基于亚磺酰基亚胺官能团的新型配体的设计和制备。特别地，报道了双（亚磺酰基）亚氨基am（siam）配体的有效和模块化的合成。合成序列的多功能性通过制备各种类似物来证明，以探索关于配体骨架的取代对催化活性的影响。siam配体在不对称催化中的效用在Cu（II）催化的Diels-Alder反应中得到了证明，其中报道了一系列N-酰基氧杂唑烷酮二烯亲和体和二烯底物组合的高度对映和非对映选择性反应。特别值得注意的是这些不对称催化剂对涉及具有挑战性和相对不反应性的无环二烯底物的反应的效率。最后，
• Vinyl cyclobutanol strategy for halogenated cyclopentanoids
  作者：Hideo Nemoto、Motohiro Shiraki、Keiichiro Fukumoto

  DOI：10.1016/0040-4039(95)01865-f

  日期：1995.11

  The iodonium ion mediated ring expansion of the olefinic cyclobutanols 19, 20, and 22 gave the mixture of iodoalkylated cyclopentanones 27a–c and 28a–c, respectively. On the other hand, the same reaction of 24 – 26 afforded stereoselectively the iodoalkylated cyclopentanones 27d and 27e.

  碘鎓离子介导的环扩展烯烃cyclobutanols的19，20，和22给iodoalkylated环戊酮的混合物27A-C和28A-C分别。在另一方面，在同一反应24 - 26立体选择性地得到iodoalkylated环戊27D和27E。