N-methoxy-N-methyl (S)-2-t-butyldiphenylsilyloxypropionamide | 116223-01-9

• 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-methoxy-N-methyl (S)-2-t-butyldiphenylsilyloxypropionamide
• 英文别名: 2-(tert-butyldiphenylsilyloxy)-N-methoxy-N-methylpropane amide；(2S)-(tert-butyldiphenylsiloxy)-N-methoxy-N-methyl-propionamide；(2S)-N-methoxy-N-methyl-2-(t-butyldiphenylsilyloxy)propanamide；(2S)-2-[tert-butyl(diphenyl)silyl]oxy-N-methoxy-N-methylpropanamide
• CAS: 116223-01-9
• 化学式: C₂₁H₂₉NO₃Si
• 分子量: 371.552
• InChiKey: LOENBOWNSQEQMP-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-methoxy-N-methyl (S)-2-t-butyldiphenylsilyloxypropionamide 在 sodium hexamethyldisilazane 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 5.11h， 生成 (S,Z)-6-(benzyloxy)-2-((tert-butyldiphenylsilyl)oxy)hex-3-en-3-yl trifluoromethanesulfonate
  参考文献：
  名称：

  eleganine A核心的立体选择性合成。

  摘要：

  首次完成了针对结构独特的细胞毒性吲哚生物碱线虫氨酸A核心的合成方法。该合成的关键步骤是将爱尔兰-克莱森立体选择性重排作为关键步骤，从而使一步即可安装2个立体异构中心和一个立体定义的双键。此外，SnCl 4促进的吲哚C-2位置的酰化作用使高度官能化的4-亚乙基脯氨酸片段与吲哚部分偶联。

  DOI：

  10.1039/d0ob00939c
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 38.75h， 生成 N-methoxy-N-methyl (S)-2-t-butyldiphenylsilyloxypropionamide
  参考文献：
  名称：

  Stereochemical diversity of AI-2 analogs modulates quorum sensing in Vibrio harveyi and Escherichia coli

  摘要：

  Bacteria coordinate population-dependent behaviors such as virulence by intra-and inter-species communication (quorum sensing). Autoinducer-2 (AI-2) regulates inter-species quorum sensing. AI-2 derives from the spontaneous cyclisation of linear (S)-4,5-dihydroxypentanedione (DPD) into two isomeric forms in dynamic equilibrium. Different species of bacteria have different classes of AI-2 receptors (LsrB and LuxP) which bind to different cyclic forms. In the present work, DPD analogs with a new stereocenter at C-5 (4,5-dihydroxyhexanediones (DHDs)) have been synthesized and their biological activity tested in two bacteria. (4S, 5R)-DHD is a synergistic agonist in Escherichia coli (which contains the LsrB receptor), while it is an agonist in Vibrio harveyi (LuxP), displaying the strongest agonistic activity reported so far (EC50 = 0.65 mu M) in this organism. Thus, modification at C-5 opens the way to novel methods to manipulate quorum sensing as a method for controlling bacteria. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.007

文献信息

• Asymmetric Synthesis of 3,4-Annulated Cyclopentenones from Cycloalkenyl Ketones and Vinyl Carbamates by Diastereoselective Carbonyl Addition/Conrotatory 4π Ring Closure
  作者：Dieter Hoppe、Michael Siemer、Roland Fröhlich

  DOI：10.1055/s-2008-1067150

  日期：2008.7

  1-Lithiated O-vinyl carbamates add with high induced diastereoselectivity onto enantiomerically pure cycloalk-1-enyl (1-dibenzylamino)alkyl ketones. Subsequent O-carbamoyl migration, followed by a torquoselective, antarafacial 4π ring closure, leads to homochiral 2-substituted bicyclo[n.3.0]alk-1-ene-2-ones.

  1-锂化O-乙烯基氨基甲酸酯以高诱导的非对映选择性与对映体纯的环烯烃(1-二苯基氨基)烷基酮发生反应。随后，O-氨基甲酰迁移，再经过扭转选择性的反面4π环闭合，生成同手性的2-取代双环[n.3.0]烷-1-烯-2-酮。
• Guanti, Giuseppe; Banfi, Luca; Narisano, Enrica, Gazzetta Chimica Italiana, 1987, vol. 117, # 11, p. 681 - 688
  作者：Guanti, Giuseppe、Banfi, Luca、Narisano, Enrica

  DOI：——

  日期：——
• Stereocontrolled palladium-catalysed umpolung allylation of aldehydes with allyl acetates
  作者：Monika Vogt、Sascha Ceylan、Andreas Kirschning

  DOI：10.1016/j.tet.2010.04.133

  日期：2010.8

  In the present work the stereocontrolled palladium-catalysed umpolung allylation of aldehydes is described. Allyl acetates are in situ transformed into the corresponding allyl boronates, which directly react with aldehydes. The question of stereocontrol is raised by employing (a) chiral boronating agents (reagent control) and by (b) utilising chiral aldehydes (substrate control). These studies reveal that the approach based on substrate control is superior to the former one with respect to yields and stereo-selectivity. Remarkably, this umpolung protocol often yields the 4,5-syn products in high selectivity, which is unprecedented for direct crotylations. (C) 2010 Elsevier Ltd. All rights reserved.
• GUANTI, GISEPPE;BANFI, LUCA;NARISANO, ENRICA, GAZZ. CHIM. ITAL., 117,(1987) N 11, 681-687
  作者：GUANTI, GISEPPE、BANFI, LUCA、NARISANO, ENRICA

  DOI：——

  日期：——