(5-甲氧基-2-硝基苯基)甲基三甲基硅烷 | 109434-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (5-甲氧基-2-硝基苯基)甲基三甲基硅烷
• 英文名称: 3-trimethylsilylmethyl-4-nitroanisole
• 英文别名: 4-nitro-3-trimethylsilylmethylanisole；4-nitro-3-<(trimethylsilyl)methyl>anisole；(5-methoxy-2-nitrobenzyl)trimethylsilane；[(5-Methoxy-2-nitrophenyl)methyl](trimethyl)silane；(5-methoxy-2-nitrophenyl)methyl-trimethylsilane
• CAS: 109434-09-5
• 化学式: C₁₁H₁₇NO₃Si
• 分子量: 239.346
• InChiKey: BFNSTEYCUTWMRY-UHFFFAOYSA-N

物化性质

• 沸点：
  310.8±27.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-甲氧基-2-硝基苯基)甲基三甲基硅烷 在 palladium diacetate 一氧化碳 、 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 20.0~70.0 ℃ 、607.95 kPa 条件下， 反应 13.25h， 生成 1-benzenesulfonyl-2-(5'-methoxyindol-2'-yl)indole
  参考文献：
  名称：

  制备吲哚并咔唑苷元和糖苷的有效策略：齐帕唑B，D，E和I的全合成。

  摘要：

  [反应：见正文]已经开发出一种有效的策略，用于快速高效地制备邻硝基苯乙烯，该邻硝基苯乙烯可以转化为不对称的2,2'-双吲哚。这些2,2'-联吲哚与（二甲基氨基）-乙醛二乙基缩醛的独特缩合可在三个合成步骤中获得替潘唑苷元生物碱的吲哚并咔唑环系，并具有优异的总收率。还讨论了吉潘唑糖苷生物碱B和E的第一个全合成。

  DOI：

  10.1021/ol035418r

文献信息

• [EN] INDOLIC DERIVATIVES AND USE THEREOF IN MEDICAL FIELD<br/>[FR] DÉRIVÉS INDOLIQUES ET UTILISATION DE CELLES-CI DANS LE DOMAINE MÉDICAL
  申请人：UNI DEGLI STUDI DL ROMA LA SAPIENZA

  公开号：WO2011121629A1

  公开（公告）日：2011-10-06

  The present invention concerns indolic derivatives and use thereof in medical field. Particularly, the invention concerns 3-[(3',4',5'- trimethoxyphenyl)thio]-1 H-indole derivatives and bioisosteric derivatives thereof and their use for the treatment of tumours.

  本发明涉及吲哚衍生物及其在医学领域中的应用。具体而言，该发明涉及3-[(3',4',5'-三甲氧基苯基)硫基]-1 H-吲哚衍生物及其生物同位素衍生物，以及它们在肿瘤治疗中的应用。
• Rapid and Efficient Synthesis of 1<i>H</i>-Indol-2-yl-1<i>H</i>-quinolin-2-ones
  作者：Jeffrey T. Kuethe、Audrey Wong、Ian W. Davies

  DOI：10.1021/ol035541i

  日期：2003.10.1

  A concise and efficient synthesis of the novel indol-2-yl-1H-quinolin-2-one ring system found in the potent and selective KDR kinase inhibitors 1-3 is presented.
• Design and Synthesis of 2-Heterocyclyl-3-arylthio-1<i>H</i>-indoles as Potent Tubulin Polymerization and Cell Growth Inhibitors with Improved Metabolic Stability
  作者：Giuseppe La Regina、Ruoli Bai、Willeke Rensen、Antonio Coluccia、Francesco Piscitelli、Valerio Gatti、Alessio Bolognesi、Antonio Lavecchia、Ilaria Granata、Amalia Porta、Bruno Maresca、Alessandra Soriani、Maria Luisa Iannitto、Marisa Mariani、Angela Santoni、Andrea Brancale、Cristiano Ferlini、Giulio Dondio、Mario Varasi、Ciro Mercurio、Ernest Hamel、Patrizia Lavia、Ettore Novellino、Romano Silvestri

  DOI：10.1021/jm2012886

  日期：2011.12.22

  New arylthioindoles (ATIs) were obtained by replacing the 2-alkoxycarbonyl group with a bioisosteric 5-membered heterocycle nucleus. The new ATIs 5, 8, and 10 inhibited tubulin polymerization, reduced cell growth of a panel of human transformed cell lines, and showed higher metabolic stability than the reference ester 3. These compounds induced mitotic arrest and apoptosis at a similar level as combretastatin A-4 and vinblastine and triggered caspase-3 expression in a significant fraction of cells in both p53-proficient and p53-defective cell lines. Importantly, ATIs 5, 8, and 10 were more effective than vinorelbine, vinblastine, and paclitaxel as growth inhibitors of the P-glycoprotein-overexpressing cell line NCI/ADR-RES. Compound 5 was shown to have medium metabolic stability in both human and mouse liver microsomes, in contrast to the rapidly degraded reference ester 3, and a pharmacokinetic profile in the mouse characterized by a low systemic clearance and excellent oral bioavailability.
• Highly chemoselective addition of (o-nitrobenzyl)silanes to nonenolizable aldehydes
  作者：Giuseppe Bartoli、Marcella Bosco、Daniele Caretti、Renato Dalpozzo、Paolo E. Todesco

  DOI：10.1021/jo00228a043

  日期：1987.9
• BARTOLI, GIUSEPPE;BOSCO, MARCELLA;CARETTI, DANIELE;DALPOZZO, RENATO;TODES+, J. ORG. CHEM., 52,(1987) N 19, 4381-4384
  作者：BARTOLI, GIUSEPPE、BOSCO, MARCELLA、CARETTI, DANIELE、DALPOZZO, RENATO、TODES+

  DOI：——

  日期：——