N,N-dibenzyliminium trifluoroacetate salt

• 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: N,N-dibenzyliminium trifluoroacetate salt
• 英文别名: dibenzylidene iminium trifluoroacetate；N,N-dibenzyliminium trifluoroacetate；Dibenzyl(methylidene)azanium;2,2,2-trifluoroacetate
• 化学式: C₂F₃O₂*C₁₅H₁₆N
• 分子量: 323.315
• InChiKey: OBQUMRHBMQXIKR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-dibenzyliminium trifluoroacetate salt 在 正丁基锂 、 四氯化钛 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 S-ethyl (2S)-2-(dibenzylamino)methyl-3-methylbutanethioate
  参考文献：
  名称：

  短杆菌肽S激发的环状混合α/β肽的合成和生物学评估。

  摘要：

  通过涉及二苄基亚胺类物质和埃文斯手性酰化恶唑烷酮的钛烯酸酯的曼尼希反应，β（2）-氨基酸（R）-和（S）-Fmoc-β（2）同卵磷脂和（R）-Fmoc-β （2）合成了高亮氨酸。这些构件与可商购的α-和β（3）-氨基酸结合使用，用于合成环-（αβ（3）αβ（2）α）（2）肽2和​​环-（ αβ（2）αβ（3）α）（2）肽3-5。筛选肽2-5抑制一小批革兰氏阴性和革兰氏阳性细菌菌株的能力。

  DOI：

  10.1002/cbdv.201200277
• 作为产物：
  描述：

  二苄胺 在 水 作用下， 生成 N,N-dibenzyliminium trifluoroacetate salt
  参考文献：
  名称：

  用于合成 β2-氨基酸的新型可扩展不对称氨基甲基化反应

  摘要：

  β-氨基酸是设计拟肽的有用工具，开发其合成的新方法，尤其是 β2-氨基酸的合成，仍然是一个重要的挑战。在这里，我们报告了一种新的可扩展路线，该路线基于 Mannich 型亚胺鎓亲电试剂对甲硅烷基乙烯酮 N,O-缩醛的氨甲基化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200600926

文献信息

• Aminomethylation of Functionalized Organozinc Reagents and Grignard Reagents Using Immonium Trifluoroacetates
  作者：Nicolas Millot、Claudia Piazza、Salvatore Avolio、Paul Knochel

  DOI：10.1055/s-2000-6307

  日期：——

  New immonium trifluoroacetates 1 and 2 react readily with functionalized organozinc or magnesium reagents leading to the corresponding aminomethylated products of type 5 and 7. The resulting bis-allylamines were deallylated leading to primary amines.

  新型亚胺盐三氟乙酸盐1和2能够与功能化的有机锌或镁试剂迅速反应，生成相应类型的氨基甲基化产物5和7。随后，双烯丙基胺经过脱烯丙基反应，得到伯胺。
• Efficient Synthesis of β²-Amino Acid by Homologation of α-Amino Acids Involving the Reformatsky Reaction and Mannich-Type Imminium Electrophile
  作者：Roba Moumne、Solange Lavielle、Philippe Karoyan

  DOI：10.1021/jo060316a

  日期：2006.4.1

  Development of new methods for the synthesis of β-amino acids is important as polymers of these compounds are promising peptidomimetic candidates in medicinal chemistry. We report here our findings on a new and highly efficient general strategy for the synthesis of β2-amino acids by homologation of α-amino acids, involving the Reformatsky reaction and Mannich-type imminium electrophile.

  合成β-氨基酸的新方法的开发是重要的，因为这些化合物的聚合物是药物化学中有希望的拟肽候选物。我们在这里报告我们发现一个新的，高效的总体战略为合成β 2 -氨基酸的α氨基酸的亿安科技，涉及reformatsky反应和曼尼希型亚铵电体。
• One-pot synthesis of β-amino acid derivatives via addition of bis(O-silyl) ketene acetals on iminium salts
  作者：Roba Moumné、Bernard Denise、Andrée Parlier、Solange Lavielle、Henri Rudler、Philippe Karoyan

  DOI：10.1016/j.tetlet.2007.09.119

  日期：2007.11

  We report here our findings on a new and highly efficient strategy for the synthesis of β-amino acids involving the addition of bis(O-silyl) ketene acetals on Mannich type iminium electrophiles.

  我们在这里报告我们关于合成β-氨基酸的新高效策略的发现，该策略涉及在曼尼希（Mannich）型亚胺基亲电体上添加双（O-甲硅烷基）乙烯酮缩醛。
• Preparation of Tertiary Amines by the Reaction of Iminium Ions Derived from Unsymmetrical Aminals with Zinc and Magnesium Organometallics
  作者：Veronika Werner、Mario Ellwart、Andreas J. Wagner、Paul Knochel

  DOI：10.1021/acs.orglett.5b00801

  日期：2015.4.17

  We report a convenient one-pot preparation of polyfunctional tertiary amines, including various biorelevant phenethylamines or ephedrine derivatives, via the reaction of new functionalized iminium ions with a variety of zinc and magnesium organometallic reagents. These iminium ions were generated from unsymmetrical aminals, obtained by the in situ addition of various amides to Tietze’s iminium salt

  我们报告了一种方便的一锅法制备的多官能叔胺，包括各种生物相关的苯乙胺或麻黄碱衍生物，它们通过新型功能化的亚胺离子与各种锌和镁有机金属试剂的反应而制得。这些亚胺离子是由不对称的缩醛生成的，这些缩醛是通过在Tietze的亚胺盐[Me 2 NCH 2 + CF 3 COO – ]中原位添加各种酰胺而获得的。通过分子内Heck反应将通过该方法制备的官能化苯胺转化为喹啉烷。
• Synthesis and Evaluation of Analogues of <i>N</i>-Phthaloyl-<scp>l</scp>-tryptophan (RG108) as Inhibitors of DNA Methyltransferase 1
  作者：Saâdia Asgatay、Christine Champion、Gaël Marloie、Thierry Drujon、Catherine Senamaud-Beaufort、Alexandre Ceccaldi、Alexandre Erdmann、Arumugam Rajavelu、Philippe Schambel、Albert Jeltsch、Olivier Lequin、Philippe Karoyan、Paola B. Arimondo、Dominique Guianvarc’h

  DOI：10.1021/jm401419p

  日期：2014.1.23

  DNA methyltransferases (DNMT) are promising drug targets in cancer provided that new, more specific, and chemically stable inhibitors are discovered. Among the non-nucleoside DNMT inhibitors, N-phthaloyl-L-tryptophan 1 (RG108) was first identified as inhibitor of DNMT1. Here, 1 analogues were synthesized to understand its interaction with DNMT. The indole, carboxylate, and phthalimide moieties were modified. Homologated and conformationally constrained analogues were prepared. The latter were synthesized from prolinohomotryptophan derivatives through a methodology based amino-zinc-ene-enolate cyclization. All compounds were tested for their ability to inhibit DNMT1 in vitro. Among them, constrained compounds 16-18 and NPys derivatives 10-11 were found to be at least 10-fold more potent than the reference compound. The cytotoxicity on the tumor, DU145 cell line of the most potent inhibitors was correlated to their inhibitory potency. Finally, docking studies were conducted in order to understand their binding mode. This study provides insights for the design of the next-generation of DNMT inhibitors.