(1,1-dimethylethyl)(4-ethenyl-2,6-dimethoxyphenoxy)dimethylsilane | 896720-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1,1-dimethylethyl)(4-ethenyl-2,6-dimethoxyphenoxy)dimethylsilane
• 英文别名: (6-t-butyldimethylsilyloxy-3,5-dimethoxy)styrene；tert-butyl-(2,6-dimethoxy-4-vinylphenoxy)-dimethyl silane；3,5-Dimethoxy-4-(t-butyldimethylsiloxy) styrene；tert-butyl-(4-ethenyl-2,6-dimethoxyphenoxy)-dimethylsilane
• CAS: 896720-93-7
• 化学式: C₁₆H₂₆O₃Si
• 分子量: 294.466
• InChiKey: SVVVNYBYYSFXJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1,1-dimethylethyl)(4-ethenyl-2,6-dimethoxyphenoxy)dimethylsilane 、 3,4,5-三甲氧基苯甲醛肟 在 sodium hypochlorite 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 25.0h， 以60%的产率得到5-(4-(tert-butyldimethylsilyloxy)-3,5-dimethoxyphenyl)-3-(3,4,5-trimethoxy-phenyl)-4,5-dihydroisoxazole
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 3,5-diaryl-isoxazoline/isoxazole-pyrrolobenzodiazepine conjugates as potential anticancer agents

  摘要：

  A series of 3,5-diaryl-isoxazoline/isoxazole linked pyrrolo[2,1-c][1,4]benzodiazepine (PBD) conjugates were prepared. These conjugates showed potent anticancer activity with GI(50) values in the range of <0.1-3.6 mu M. Some of these PBD conjugates (6a-c) with promising anticancer activity were further investigated on the cell cycle distribution. Moreover, these PBD conjugates exhibited G0/G1 arrest, enhancement in the levels of p53 protein as well as mitochondrial-mediated intrinsic pathway, leading to release of cytochrome c, activation of caspase-3, cleavage of PARP and subsequent apoptotic cell death. Hence these PBD conjugates with 6a being the most potent one could be be taken up for preclinical studies either alone or in combination with existing therapies. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.047
• 作为产物：
  描述：

  丁香醛 在 咪唑 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.58h， 生成 (1,1-dimethylethyl)(4-ethenyl-2,6-dimethoxyphenoxy)dimethylsilane
  参考文献：
  名称：

  Synthesis of the 5-hydroxymethyl-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural products descurainin and cartorimine

  摘要：

  Reaction of pyranulose 6 with styrenes 12c or 13 and Et3N in CH2O2 at 25 degrees C afforded the [5+2] cycloadducts 14c and 15, which were hydrolyzed to give the natural products I and descurainin (2) in 24 and 27% overall yield, respectively. Heating pyranulose 6 with cinnamate ester 21 in the presence of 2,6-di-t-butylpyridine in CH3CN at 175 degrees C afforded the [5+2] cycloadduct, which was hydrolyzed to give cartorimine (3) in 13% yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.083

文献信息

• Bio‐based vinylphenol family: Synthesis via decarboxylation of naturally occurring cinnamic acids and living radical polymerization for functionalized polystyrenes
  作者：Hisaaki Takeshima、Kotaro Satoh、Masami Kamigaito

  DOI：10.1002/pola.29453

  日期：2020.1

  weight distributions. Subsequent deprotection of the silyl groups under mild conditions results in a series of well‐defined functionalized polystyrenes possessing different numbers (mono‐, di‐, tri‐) of hydroxy groups at different positions (o, m, p). The obtained functionalized polystyrenes show unique thermal properties depending on the substituents, and those with phenol and catechol groups serve

  通过将各种天然存在的肉桂酸（例如o，m和p）简单地脱羧，可以制备一系列生物基乙烯基苯酚或羟基苯乙烯。-香豆; 咖啡的 阿魏的 和芥子酸，其在芳环的不同位置具有羟基和其他取代基。用三烷基甲硅烷基保护酚基部分后，用二硫代苯甲酸枯基酯完成可逆的加成-断裂链转移聚合反应，从而得到分子量可控且分子量分布窄的各种生物基羟基保护的聚苯乙烯。随后在温和条件下对甲硅烷基基团进行脱保护，得到一系列定义明确的官能化聚苯乙烯，它们在不同位置（o，m，p处具有不同数量（单，二，三）羟基）。所获得的官能化聚苯乙烯根据取代基显示出独特的热性能，并且具有苯酚和邻苯二酚基团的那些充当银离子的还原剂。©2019 Wiley Periodicals，Inc.J.Polym。科学 2020，58，91-100
• Efficient generation of an oxidopyrylium ylide using a Pd catalyst and its [5+2] cycloadditions with several dipolarophiles
  作者：Hiroyuki Suga、Taichi Iwai、Masahiro Shimizu、Kie Takahashi、Yasunori Toda

  DOI：10.1039/c7cc09552j

  日期：——

  6-acetoxy-6-acetoxymethyl-2H-pyran-3(6H)-one using a Pd catalyst and [5+2] cycloadditions of the resulting ylide are described. Among substituted styrene derivatives as dipolarophiles, electron-rich styrenes showed higher yield (up to 80%). The [5+2] cycloaddition reactions can also be applied to exo-methylene cyclic compounds, and an improved method for the synthesis of polygalolide intermediate has been

  描述了使用Pd催化剂从6-乙酰氧基-6-乙酰氧基甲基-2 H-吡喃-3（6 H）-1生成氧化吡啶鎓叶立德的有效方法，以及所得的叶立德的[5 + 2]环加成。在取代的苯乙烯衍生物（如双极性亲和剂）中，富电子苯乙烯显示出更高的收率（高达80％）。[5 + 2]环加成反应也可以用于外亚甲基环状化合物，并且已经证明了一种改进的合成聚没食子酸酯中间体的方法。
• Triethylamine Enables Catalytic Generation of Oxidopyrylium Ylides for [5+2] Cycloadditions with Alkenes: An Efficient Entry to 8-Oxabicyclo[3.2.1]octane Frameworks
  作者：Yasunori Toda、Masahiro Shimizu、Taichi Iwai、Hiroyuki Suga

  DOI：10.1002/adsc.201800290

  日期：2018.6.15

  of 8‐oxabicyclo[3.2.1]octane derivatives including synthetic intermediates of natural products is described, in which triethylamine effectively catalyzes [5+2] cycloaddition reactions between oxidopyrylium ylides and alkenes. This method can be applied not only to intermolecular cycloadditions with various alkenes but also to intramolecular cycloadditions. The key finding is that the combined use of

  描述了一种制备包括天然产物合成中间体在内的一系列8-氧杂双环[3.2.1]辛烷衍生物的有效方法，其中三乙胺有效地催化了氧化吡啶鎓内酯与烯烃之间的[5 + 2]环加成反应。该方法不仅可以应用于具有各种烯烃的分子间环加成，而且可以应用于分子内环加成。关键发现是将具有适当碱性的有机碱与带有合适离去基团的氧化吡啶鎓前体组合使用可促进碱式氧化吡啶鎓的催化生成。
• Synthesis of the 5-hydroxymethyl-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural products descurainin and cartorimine
  作者：Barry B. Snider、James F. Grabowski

  DOI：10.1016/j.tet.2005.10.083

  日期：2006.5

  Reaction of pyranulose 6 with styrenes 12c or 13 and Et3N in CH2O2 at 25 degrees C afforded the [5+2] cycloadducts 14c and 15, which were hydrolyzed to give the natural products I and descurainin (2) in 24 and 27% overall yield, respectively. Heating pyranulose 6 with cinnamate ester 21 in the presence of 2,6-di-t-butylpyridine in CH3CN at 175 degrees C afforded the [5+2] cycloadduct, which was hydrolyzed to give cartorimine (3) in 13% yield. (c) 2006 Elsevier Ltd. All rights reserved.
• Design, synthesis and biological evaluation of 3,5-diaryl-isoxazoline/isoxazole-pyrrolobenzodiazepine conjugates as potential anticancer agents
  作者：Ahmed Kamal、J. Surendranadha Reddy、M. Janaki Ramaiah、D. Dastagiri、E. Vijaya Bharathi、M. Ameruddin Azhar、Farheen Sultana、S.N.C.V.L. Pushpavalli、Manika Pal-Bhadra、Aarti Juvekar

  DOI：10.1016/j.ejmech.2010.05.047

  日期：2010.9

  A series of 3,5-diaryl-isoxazoline/isoxazole linked pyrrolo[2,1-c][1,4]benzodiazepine (PBD) conjugates were prepared. These conjugates showed potent anticancer activity with GI(50) values in the range of <0.1-3.6 mu M. Some of these PBD conjugates (6a-c) with promising anticancer activity were further investigated on the cell cycle distribution. Moreover, these PBD conjugates exhibited G0/G1 arrest, enhancement in the levels of p53 protein as well as mitochondrial-mediated intrinsic pathway, leading to release of cytochrome c, activation of caspase-3, cleavage of PARP and subsequent apoptotic cell death. Hence these PBD conjugates with 6a being the most potent one could be be taken up for preclinical studies either alone or in combination with existing therapies. (C) 2010 Elsevier Masson SAS. All rights reserved.