1,3,5-三二苯甲基-1,3,5-噻嗪烷 | 91290-81-2

• 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: 1,3,5-三二苯甲基-1,3,5-噻嗪烷
• 英文名称: 1,3,5-tris(diphenylmethyl)-hexahydro-1,3,5-triazine
• 英文别名: 1,3,5-tris(benzhydryl)hexahydro-1,3,5-triazine；1,3,5-tris(diphenylmethyl)hexahydro-s-triazine；2,4,6-tris(benzhydryl)hexahydro-1,3,5-triazine；tris(diphenylmethyl)hexahydro-1,3,5-triazine；1,3,5-tribenzhydryl-hexahydro-1,3,5-triazin；1,3,5-tribenzhydryl-hexahydro-S-triazine；1,3,5-Tribenzhydryl-1,3,5-triazinane
• CAS: 91290-81-2
• 化学式: C₄₂H₃₉N₃
• 分子量: 585.792
• InChiKey: SGHJAMVUKGYVQK-UHFFFAOYSA-N

物化性质

• 沸点：
  657.4±55.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,5-三二苯甲基-1,3,5-噻嗪烷 在 次磷酸 、 盐酸 、 methyloxirane 作用下， 生成 aminomethyl-bis(H-phosphinic acid)
  参考文献：
  名称：

  WO2007/62376

  摘要：

  公开号：
• 作为产物：
  描述：

  聚合甲醛 、 二苯甲胺 在 potassium hydroxide 作用下， 生成 1,3,5-三二苯甲基-1,3,5-噻嗪烷
  参考文献：
  名称：

  基于次磷酸盐的次膦酸的合成方法：VIII。α-氨基烷基苯乙基次膦酸的合成

  摘要：

  基于次磷酸盐的双Arbuzov重排方法的发展，通过逐步将中间形成的三价磷的甲硅烷基酯添加到不同的不饱和化合物中的Michael-Pudovik型反应，可以一锅形成两个不对称的磷-碳键。开发了α-氨基烷基苯乙基次膦酸的合成方法。双（三甲基硅烷基）亚磷酸酯是由于将双（三甲基硅烷基）亚磷酸酯原位添加到苯乙烯中而形成的将其不从反应混合物中分离地加入到由苄胺或二苯甲胺和各种醛初步获得的席夫碱中。随后通过氢化或酸性水解除去N-保护基团得到许多新的α-氨基烷基苯乙基次膦酸。

  DOI：

  10.1134/s107036321109009x
• 作为试剂：
  描述：

  ethyl diethoxymethylphosphinate 在 1,3,5-三二苯甲基-1,3,5-噻嗪烷 、 水 、 氢溴酸 作用下， 以 甲苯 为溶剂， 生成 aminomethyl-bis(H-phosphinic acid)
  参考文献：
  名称：

  Phosphinic Peptide Matrix Metalloproteinase-9 Inhibitors by Solid-Phase Synthesis Using a Building Block Approach

  摘要：

  The solid-phase synthesis of an array of different pseudopeptides containing a phosphinic glycine-leucine moiety (-G Psi/{P(O)OH-CH2}L-)([1]) is described. The resulting pseudopeptides were shown to act as matrix metalloproteinase-9 (MMP-9) inhibitors. Starting from available materials, the protected amino acid isosters benzyloxy-carbonyl aminomethylphosphinic acid (glycine analogue) and ethyl alpha-isobutylacrylate (leucine analogue) were synthesized and coupled with the bis(trimethylsilyl)phosphonite. Protective group interchange yielded a protected phosphinic dipeptide building block 1 ready for use in solid-phase peptide synthesis, Solid-phase peptide synthesis was performed with 9-fluorenylmethyloxycarbonyl (Fmoc) chemistry on a polyethylene glycol polyamide (PEGA) support and the coupling of 1 (1.5 equiv) was carried out with standard activation. The P-4-P-2 and P-2'-P-4' positions of the pseudopeptides were designed by analogy of the cleavage sequences of different natural extracellular matrix protein substrates with a synthetic peptide substrate of MMP-9. The crude peptides were obtained in high yield and purity as determined by RP-HPLC, and were characterized by electrospray mass spectrometry and amino acid analysis after purification. Enzyme kinetic investigations with MMP-9 of the purified peptide inhibitors showed Ki values in the range from mM to nM.

  DOI：

  10.1002/(sici)1521-3765(19991001)5:10<2877::aid-chem2877>3.0.co;2-z

文献信息

• Pentanidium-Catalyzed Enantioselective Phase-Transfer Conjugate Addition Reactions
  作者：Ting Ma、Xiao Fu、Choon Wee Kee、Lili Zong、Yuanhang Pan、Kuo-Wei Huang、Choon-Hong Tan

  DOI：10.1021/ja1098353

  日期：2011.3.9

  A new chiral entity, pentanidium, has been shown to be an excellent chiral phase-transfer catalyst. The enantioselective Michael addition reactions of tert-butyl glycinate-benzophenone Schiff base with various α,β-unsaturated acceptors provide adducts with high enantioselectivities. A successful gram-scale experiment at a low catalyst loading of 0.05 mol % indicates the potential for practical applications

  一种新的手性实体戊烷已被证明是一种出色的手性相转移催化剂。甘氨酸叔丁酯-二苯甲酮席夫碱与各种α,β-不饱和受体的对映选择性迈克尔加成反应提供了具有高对映选择性的加合物。在 0.05 mol% 的低催化剂负载下成功的克级实验表明该方法具有实际应用的潜力。磷酸甘氨酸酯类似物也可用作迈克尔供体，提供富含对映体的 α-氨基膦酸衍生物和 (S)-脯氨酸的膦酸类似物。
• Gold-catalyzed sequential annulations towards 3,4-fused bi/tri-cyclic furans involving a [3+2+2]-cycloaddition
  作者：Suna Liu、Pu Yang、Shiyong Peng、Chenghao Zhu、Shengyu Cao、Jian Li、Jiangtao Sun

  DOI：10.1039/c6cc09154g

  日期：——

  A gold-catalyzed sequential annulation towards 3,4-fused bicyclic furan compounds has been realized by employing 2-(1-alkynyl)-2-alken-1-ones and 1,3,5-triazines as the starting materials under mild reaction conditions. This protocol features the multiple...

  通过以2-（1-炔基）-2-烯烃-1-酮和1,3,5-三嗪为起始原料在温和反应下实现了金催化的3,4-稠合双环呋喃化合物的连续环化反应条件。该协议具有多个...
• Catalyst-free synthesis of tetrahydropyrimidines <i>via</i> formal [3+3]-cycloaddition of imines with 1,3,5-hexahydro-1,3,5-triazines
  作者：Long Chen、Kai Liu、Jiangtao Sun

  DOI：10.1039/c7ra11973a

  日期：——

  tetrahydropyrimidines from readily available starting materials has been developed. This process features an unprecedented intermolecular formal [3+3]-annulation of imines and 1,3,5-hexahydro-1,3,5-triazines under catalyst-free conditions. Importantly, differing from previous transformations, the 1,3,5-triazines are firstly utilized as formal 1,3-dipoles in cycloaddition reactions.

  已经开发了一种从容易获得的起始材料合成多取代四氢嘧啶的实用且环境友好的方法。该过程的特点是在无催化剂条件下对亚胺和 1,3,5-hexahydro-1,3,5-triazines 进行前所未有的分子间形式 [3+3]-环化。重要的是，与之前的转化不同，1,3,5-三嗪首先在环加成反应中用作正式的 1,3-偶极子。
• Synthese und Struktur von Zink-Komplexen von 2-Amino-1-azetinen
  作者：Friedrich Stierli、Roland Prewo、Jost H. Bieri、Heinz Hemigartner

  DOI：10.1002/hlca.19840670402

  日期：1984.6.20

  Synthesis ad Structure of Zinc Complexes of 2-Amino-1-azetines

  2-氨基-1-金刚烷锌配合物的合成和结构
• Palladium-Catalyzed Ligand-Directed Divergent Decarboxylative Cycloadditions of Vinyloxazolidine-2,4-diones with 1,3,5-Triazinanes
  作者：Zhen-Hua Wang、Xiao-Hui Fu、Qun Li、Jian-Qiang Zhao、Yong You、Yan-Ping Zhang、Wei-Cheng Yuan

  DOI：10.1021/acs.orglett.3c04339

  日期：2024.3.1

  regiodivergent ligand-controlled palladium-catalyzed cycloaddition reaction of vinyloxazolidine-2,4-diones with 1,3,5-triazinanes. In the presence of a diphosphine ligand, the reaction proceeds via a (5+2) cycloaddition pathway to afford 1,3-diazepin-4-ones in excellent yields, while using a monophosphine ligand, the reaction proceeds smoothly via a (3+2) cycloaddition pathway to give imidazolidin-4-ones

  本研究展示了乙烯基恶唑烷-2,4-二酮与 1,3,5-三嗪烷的高效区域发散配体控制的钯催化环加成反应。在二膦配体存在下，反应通过(5+2)环加成途径进行，以优异的收率得到1,3-二氮杂卓-4-酮，而使用单膦配体时，反应通过(3+ 2)环加成途径以良好的产率得到咪唑烷-4-酮。