dibenzyl naphthalene-2,6-dicarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dibenzyl naphthalene-2,6-dicarboxylate
• 英文别名: 2,6-Naphathalenedicarboxylic acid dibenzyl ester
• 化学式: C₂₆H₂₀O₄
• 分子量: 396.442
• InChiKey: VDKNYFDZDJTKCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲醇 、 2,6-萘二羧酸二甲酯 在 对甲苯磺酸 作用下， 生成 dibenzyl naphthalene-2,6-dicarboxylate
  参考文献：
  名称：

  Chemistry and Stereochemistry of Benzyl-Benzyl Interactions in MH+ Ions of Dibenzyl Esters upon Chemical Ionization and Collision-induced Dissociation Conditions

  摘要：

  Isobutane chemical ionization mass spectra of dibenzyl esters of a wide variety of aliphatic, olefinic, alicyclic and aromatic dicarboxylic acids exhibit abundant m/z 181 C14H13+ ions, indicating a highly general rearrangement process involving the formation of a new bond between the two benzyl groups. An extensive collision-induced dissociation and deuterium labeling study suggested that these ions are an almost equimolar mixture of isomeric alpha-o-tolylbenzyl, alpha-p-tolylbenzyl and p-benzylbenzyl cation structures, and this composition is identical for all the diesters examined This structural assignment of the C14H13+ ions suggests a mechanistic pathway for their generation, based on the formation of the new bond between tbe benzyl methylene group of the protonated benzoxycarbonyl and the phenyl ring of the otter ester moiety via pi- (and/or ion-neutral) and a-complexes. Stereoisomeric diesters show an unusual steric effect: trans-isomers give rise to much more abundant C14H13+ ions than the cis counterparts, This behavior is explained by stabilized proton-bridged structures of the MH+ ions of the cis-isomers. (C) 1997 by John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1096-9888(199705)32:5<515::aid-jms504>3.0.co;2-b

文献信息

• Ynoate-Initiated Selective C–N Esterification of Tertiary Amines under Transition-Metal and Oxidant-Free Conditions
  作者：Huangdi Feng、Junhai Huang、Feixiang Sun、Liliang Huang

  DOI：10.1055/a-1326-6973

  日期：2021.4

  An efficient and selective method for metal- and oxidant-free deaminated esterification of tertiary amines is presented. In this protocol, ynoates play a key role to activate the Csp3−N bond through a process of in situ generation of zwitterionic salts. The transformations show that Csp3−N bond in the zwitterionic species has a lower dissociation energy than Csp2−N bond, leading to break preferentially

  提出了一种用于叔胺的无金属和无氧化剂的脱氨基酯化的有效和选择性方法。在该协议中，ynoates 通过原位生成两性离子盐的过程在激活 Csp3-N 键方面发挥着关键作用。转化表明，两性离子物种中的 Csp3-N 键具有比 Csp2-N 键低的离解能，导致优先断裂并被羧酸捕获，以中等至良好的产率生成相应的产物。
• Phosphate mimics and methods of treatment using phosphatease inhibitors
  申请人：Sugen, Inc.

  公开号：US20040138255A1

  公开（公告）日：2004-07-15

  The invention relates to trifluoromethyl sulfonyl and trifluoromethyl sulfonamido compounds and the physiologically acceptable salts and the prodrugs thereof. These compounds are expected to modulate the activity of protein tyrosine enzymes which are related to cellular signal transduction, in particular, protein tyrosine phosphatase, and therefore are expected to be useful in the prevention and treatment of disorders associated with abnormal protein tyrosine enzyme related cellular signal transduction such as cancer, diabetes, immuno-modulation, neurologic degenerative diseases, osteoporosis and infectious diseases. The invention also relates to the use of compounds containing fluoromethyl sulfonyl groups as phosphate mimics. These mimics may be used to inhibit, regulate or modulate the activity of a phosphate binding protein in a cell.

  本发明涉及三氟甲基磺酰和三氟甲基磺酰胺化合物及其生理上可接受的盐和前药。这些化合物预计能够调节与细胞信号转导相关的蛋白酪氨酸酶的活性，特别是蛋白酪氨酸磷酸酶，因此预计在预防和治疗与异常蛋白酪氨酸酶相关的细胞信号转导障碍，如癌症、糖尿病、免疫调节、神经退行性疾病、骨质疏松症和传染病方面有用。本发明还涉及含有氟甲基磺酰基团的化合物作为磷酸酯模拟物的用途。这些模拟物可用于抑制、调节或调节细胞中的磷酸结合蛋白的活性。
• Phosphate mimics and methods of treatment using phosphatase inhibitors
  申请人：Sugen, Inc.

  公开号：US06596772B1

  公开（公告）日：2003-07-22

  The invention relates to trifluoromethyl sulfonyl and trifluoromethyl sulfonamido compounds and the physiologically acceptable salts and the prodrugs thereof. These compounds are expected to modulate the activity of protein tyrosine enzymes which are related to cellular signal transduction, in particular, protein tyrosine phosphatase, and therefore are expected to be useful in the prevention and treatment of disorders associated with abnormal protein tyrosine enzyme related cellular signal transduction such as cancer, diabetes, immuno-modulation, neurologic degenerative diseases, osteoporosis and infectious diseases. The invention also relates to the use of compounds containing fluoromethyl sulfonyl groups as phosphate mimics. These mimics may be used to inhibit, regulate or modulate the activity of a phosphate binding protein in a cell.

  本发明涉及三氟甲基磺酰和三氟甲基磺酰胺化合物及其生理上可接受的盐和前药。这些化合物预计能够调节与细胞信号转导相关的蛋白酪氨酸酶的活性，尤其是蛋白酪氨酸磷酸酶，因此预计能够在预防和治疗与异常蛋白酪氨酸酶相关的细胞信号转导紊乱的疾病，如癌症、糖尿病、免疫调节、神经退行性疾病、骨质疏松症和传染病方面有用。本发明还涉及含有氟甲基磺酰基团的化合物作为磷酸盐类似物的用途。这些类似物可用于抑制、调节或调节细胞中的磷酸盐结合蛋白的活性。
• Structure-based design and synthesis of small molecule protein–tyrosine phosphatase 1B inhibitors
  作者：Zhu-Jun Yao、Bin Ye、Xiong-Wu Wu、Shaomeng Wang、Li Wu、Zhong-Yin Zhang、Terrence R. Burke

  DOI：10.1016/s0968-0896(98)00140-0

  日期：1998.10

  Protein-tyrosine phosphatase (PTP) inhibitors are attractive as potential signal transduction-directed therapeutics which may be useful in the treatment of a variety of diseases. We have previously reported the X-ray structure of 1,1-difluoro-1-(2-naphthalenyl)methyl] phosphonic acid (4) complexed with the human the protein-tyrosine phosphatase 1B (PTP1B) and its use in the design of an analogue which binds with higher affinity within the catalytic site (Burke, T. R., Jr. et al. Biochemistry 1996, 35, 15989). In the current study, new naphthyldifluoromethyl phosphonic acids were designed bearing acidic functionality intended to interact with the PTP1B Arg47, which is situated just outside the catalytic pocket. This residue has been shown previously to provide key interactions with acidic residues of phosphotyrosyl-containing peptide substrates. Consistent with trends predicted by molecular dynamics calculations, the new analogues bound with 7- to 14-fold higher affinity than the parent 4, in principal validating the design rationale. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Strey, Karsten; Voes, Juergen, Journal of Chemical Research, Miniprint, 1998, # 3, p. 648 - 682
  作者：Strey, Karsten、Voes, Juergen

  DOI：——

  日期：——