1,3,5-tris(((tert-butyldimethylsilyl)oxy)methyl)benzene | 883893-69-4

• 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: 1,3,5-tris(((tert-butyldimethylsilyl)oxy)methyl)benzene
• 英文别名: [3,5-Bis[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]methoxy-tert-butyl-dimethylsilane
• CAS: 883893-69-4
• 化学式: C₂₇H₅₄O₃Si₃
• 分子量: 510.98
• InChiKey: RHNJJMYMPBEODH-UHFFFAOYSA-N

物化性质

• 沸点：
  481.3±40.0 °C(Predicted)
• 密度：
  0.909±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.25
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  1,3,5-tris(((tert-butyldimethylsilyl)oxy)methyl)benzene 在 palladium on activated charcoal 吡啶 、 amberlyst-15 、 硝酸 、 ammonium formate 、 乙酸酐 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Remarkable drug-release enhancement with an elimination-based AB3 self-immolative dendritic amplifier

  摘要：

  Self-immolative dendritic prodrugs, activated through a single catalytic reaction by a specific enzyme, could offer significant advantages in inhibition of tumor growth relative to monomeric prodrug, especially if the targeted or secreted enzyme exists at relatively low levels in the malignant tissue. We have designed and synthesized new AB(3) self-immolative dendritic prodrug system that releases three active drugs by a single cleavage of the enzyme penicillin-G-amidase. The cleavage signal is transferred from the dendron focal point to its periphery through fast elimination reactions and the design leads to three-fold signal amplification. In cell-growth inhibition assays, the elimination-based AB(3) self-immolative dendritic prodrug was significantly more effective than a cyclization-based AB(3) dendritic prodrug. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.054
• 作为产物：
  描述：

  均三苄醇 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以68%的产率得到1,3,5-tris(((tert-butyldimethylsilyl)oxy)methyl)benzene
  参考文献：
  名称：

  Remarkable drug-release enhancement with an elimination-based AB3 self-immolative dendritic amplifier

  摘要：

  Self-immolative dendritic prodrugs, activated through a single catalytic reaction by a specific enzyme, could offer significant advantages in inhibition of tumor growth relative to monomeric prodrug, especially if the targeted or secreted enzyme exists at relatively low levels in the malignant tissue. We have designed and synthesized new AB(3) self-immolative dendritic prodrug system that releases three active drugs by a single cleavage of the enzyme penicillin-G-amidase. The cleavage signal is transferred from the dendron focal point to its periphery through fast elimination reactions and the design leads to three-fold signal amplification. In cell-growth inhibition assays, the elimination-based AB(3) self-immolative dendritic prodrug was significantly more effective than a cyclization-based AB(3) dendritic prodrug. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.054

文献信息

• A Highly Practical <i>Instant</i> Catalyst for Cyclotrimerization of Alkynes to Substituted Benzenes
  作者：Naoko Saino、Fumihiro Amemiya、Emi Tanabe、Kouki Kase、Sentaro Okamoto

  DOI：10.1021/ol0602295

  日期：2006.3.1

  see text] A 2-(2,6-diisopropylphenyl)iminomethylpyridine (1a)/CoCl(2).6H(2)O/Zn reagent has been developed as an effective instant catalyst for the intra- and intermolecular cyclotrimerization of alkynes to substituted benzenes, making the method extremely practical since the reagent, 1a/CoCl(2).6H(2)O/Zn, is inexpensive and easy to handle and the reaction is less sensitive to moisture and is reasonably

  [反应：见正文] 2-（2,6-二异丙基苯基）亚氨基甲基吡啶（1a）/ CoCl（2）.6H（2）O / Zn试剂已被开发为一种有效的即时催化剂，用于分子内和分子间环三聚炔烃与取代的苯反应，使该方法极为实用，因为1a / CoCl（2）.6H（2）O / Zn试剂价格低廉且易于处理，并且反应对水分的敏感性较低，并且反应一般。
• Iron-catalyzed regioselective cyclotrimerization of alkynes to benzenes
  作者：Suhas Shahaji Gawali、Chidambaram Gunanathan

  DOI：10.1016/j.jorganchem.2018.12.007

  日期：2019.2

  catalyzed the regioselective [2+2+2] cyclotrimerization of terminal aryl and alkyl alkynes to provide the 1,2,4-trisubstituted benzene molecules. Interestingly, internal alkynes also exhibited similar cyclization and resulted in hexa-substituted benzene compounds. Increased steric bulk on pincer ligands diminished the selectivity for cycloaddition. Cyclotrimerization reactions proceeded at room temperature

  我们报告了简单的二（氨基甲基）吡啶连接的铁-钳配合物的合成和表征，它催化了末端芳基和烷基炔烃的区域选择性[2 + 2 + 2]环三聚反应，从而提供了1,2,4-三取代的苯分子。有趣的是，内部炔烃也表现出相似的环化作用，并产生六取代的苯化合物。钳位配体上增加的空间体积减少了对环加成反应的选择性。在通过格氏试剂活化催化剂后，在室温下进行环三聚反应。EPR研究表明，在催化剂中热诱导的自旋交叉效应。
• Exploiting Guanidine as a Ligand in Cobalt-Catalyzed Alkyne Cyclotrimerizations
  作者：James Stambuli、Chad Eichman、Jason Bragdon

  DOI：10.1055/s-0030-1259931

  日期：2011.5

  The synthesis of polysubstituted arenes is accomplished via the regioselective cyclotrimerization of alkynes utilizing a guanidine-ligated cobalt catalyst.

  多取代芳烃的合成是通过炔烃的区域选择性环三聚反应来完成的，使用胍连接的钴催化剂。
• A Versatile, Functional Group‐Tolerant, and Bench‐Stable Iron Precatalyst for Building Arene and Triazine Rings by [2+2+2] Cycloadditions
  作者：William Parisot、Mansour Haddad、Phannarath Phansavath、Guillaume Lefèvre、Virginie Ratovelomanana‐Vidal

  DOI：10.1002/chem.202400096

  日期：2024.4.16

  A new [2+2+2] cycloaddition procedure relying on the use of an air-stable iron precatalyst is described, which allows the construction of aromatic and nitrogen-containing heteroaromatic rings in green solvents and mild conditions. Cycloadditions and cross-cycloadditions between 1,6- or 1,7-diynes and alkynes are reported, with a broad functional tolerance, leading to a variety of functionalizable scaffolds

  描述了一种依赖于使用空气稳定的铁预催化剂的新的[2+2+2]环加成过程，该过程允许在绿色溶剂和温和条件下构建芳香环和含氮杂芳环。据报道，1,6-或1,7-二炔与炔之间的环加成和交叉环加成具有广泛的功能耐受性，从而产生各种可功能化的支架。
• H-BPin/KO^<i>t</i>Bu Promoted Activation of Cobalt Salt to a Heterotopic Catalyst for Highly Selective Cyclotrimerization of Alkynes
  作者：Shuo Song、Chuhan Li、Tianfen Liu、Panke Zhang、Xiaoming Wang

  DOI：10.1021/acs.orglett.1c02493

  日期：2021.9.3