bis(1,1-dimethylethyl) 1,5,9-triazacyclododecane-1,5-dicarboxylate | 174192-40-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bis(1,1-dimethylethyl) 1,5,9-triazacyclododecane-1,5-dicarboxylate
• 英文别名: 5,9-di-tert-butyl 1,5,9-triazacyclododecane-5,9-dicarboxylate；1,5-bis(tert-butoxycarbonyl)-1,5,9-triazacyclododecane；ditert-butyl 1,5,9-triazacyclododecane-1,5-dicarboxylate
• CAS: 174192-40-6
• 化学式: C₁₉H₃₇N₃O₄
• 分子量: 371.52
• InChiKey: VQZOHTBLIFUGSM-UHFFFAOYSA-N

物化性质

• 沸点：
  463.6±40.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  71.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bis(1,1-dimethylethyl) 1,5,9-triazacyclododecane-1,5-dicarboxylate 在 盐酸 、 sodium tungstate 、 titanium(III) chloride 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 43.25h， 生成 bis(1,1-dimethylethyl) 8-cyano-1,5,9-triazacyclododecane-1,5-dicarboxylate
  参考文献：
  名称：

  Conversion of Macrocyclic Polyamines into Carbon-Substituted Derivatives. Synthesis of Derivatives of 1,5,9-Triazacyclododecane-2-carbonitrile

  摘要：

  DOI：

  10.1021/jo951637h
• 作为产物：
  描述：

  Ditert-butyl 9-benzyl-1,5,9-triazacyclododecane-1,5-dicarboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、607.95 kPa 条件下， 反应 96.0h， 以100%的产率得到bis(1,1-dimethylethyl) 1,5,9-triazacyclododecane-1,5-dicarboxylate
  参考文献：
  名称：

  Conversion of Macrocyclic Polyamines into Carbon-Substituted Derivatives. Synthesis of Derivatives of 1,5,9-Triazacyclododecane-2-carbonitrile

  摘要：

  DOI：

  10.1021/jo951637h

文献信息

• 基于四苯乙烯基的Gemini型两亲性化合物及 其制备方法和用途
  申请人：北京师范大学

  公开号：CN106432203B

  公开（公告）日：2019-04-09

  本发明公开一种基于四苯乙烯基的Gemini型两亲性化合物及其制备方法和用途。本发明公开的化合物主要通过McMurry偶联反应、亲核取代反应和Click反应制备，其结构也通过红外、核磁和质谱确认；在水溶液中，本发明公开的化合物的衍生物分子自组装形成聚集诱导荧光增强的胶束(AIE micelles)；而与核酸作用后会共聚集形成易于细胞摄取的纳米颗粒；绿色荧光蛋白(GFP)和荧光素酶(Luciferase)表达实验证明了这种化合物本身以及与二油酰磷脂酰乙醇胺(DOPE)形成的脂质体可以作为非病毒基因载体；同时我们利用这类化合物自组装和与DNA的共组装的可逆性转变成功的将此种衍生物用于示踪pGL‑3和FAM‑DNA的细胞摄取和释放过程。
• Synthesis of mono- and di-[12]aneN3 ligands and study on the catalytic cleavage of RNA model 2-hydroxypropyl-p-nitrophenyl phosphate with their metal complexes
  作者：Zhi-Fo Guo、Hao Yan、Zhi-Fen Li、Zhong-Lin Lu

  DOI：10.1039/c1ob05942d

  日期：——

  The ortho arrangement of the two [12]aneN3 units and the presence of 5- or 2-positioned substituents in the benzene ring as well as N-methylation of [12]aneN3 units greatly reduced the catalytic activities due to the steric effects. These results clearly indicate that the structures of the linker between two [12]aneN3 units play very important role in their catalytic synergistic effects.

  一系列的单-和二- [12] ANEN 3个配体1-6，其含有之间的协调骨架不同的取代基，不同接头2 [12] ANEN 3单元和不同Ñ -methylation上的[12] ANEN 3单位，已经合成并充分表征。它们的金属配合物对RNA模型磷酸2-羟丙基-对硝基苯基磷酸酯（HPNPP）裂解的催化活性随配体和金属离子的结构而变化。点击反应提供了一种有效的方法来制备一系列[12] aneN 3但是，由于三唑部分与金属离子的配位以及对三氟甲磺酸酯抗衡离子的强抑制作用，三唑部分的引入降低了催化活性。双核锌（II含有）络合物米-二甲苯桥表现出与协同作用到更高的催化活性700倍。具有三唑部分的配体的铜（II）配合物被证明具有高反应活性，并且在两个铜（II）离子之间显示出很强的协同性。来讲ķ 2，双核配合物的Zn 2 -图3b，锌2 - 3D，锌2 - 4B，和Cu2 -图4b的7.9×10得到活动5，3
• Tripodal, Cooperative, and Allosteric Transphosphorylation Metallocatalysts
  作者：Alessandro Scarso、Giovanni Zaupa、Florence Bodar Houillon、Leonard J. Prins、Paolo Scrimin

  DOI：10.1021/jo061754k

  日期：2007.1.1

  amounts of ZnII show that the complexes represent minimalist examples of metallocatalysts with cooperativity between the metal centers and allosteric control by a metal ion. The Tren binding site constitutes the allosteric regulation unit, while the three ZnII−azacrown complexes provide the cooperative, catalytic site. The allosteric role of the ZnII ion located in the Tren binding site was unambiguously

  通过分别用1,4,7-三氮杂环壬烷，1,5,9-三氮杂环十二烷和1,4,7,10-四氮杂环十二烷取代羟基部分而衍生自1-丝氨酸的三个人工氨基酸已与这三个氨基酸连接四胺三（2-氨基乙基）胺，Tren的臂，以获得三脚架配体。它们能够结合多达四个金属离子（如Cu II和Zn II），其中三个与多氮杂大环结合，一个与Tren平台结合。这些三脚架配体的某些Zn II配合物被证明是裂解RNA模型底物2-羟丙基-对硝基苯基磷酸酯（HPNP）的良好催化剂。Zn II含量增加时的催化活性研究结果表明，该配合物代表了金属催化剂的极简主义实例，在金属中心之间具有协同作用，并且通过金属离子进行变构控制。Tren结合位点构成了变构调节单元，而三个Zn II-氮杂卓复合物提供了协同的催化位点。通过研究无法在该位点络合Zn II的衍生物的催化活性，可明确证明位于Tren结合位点的Zn II离子的变构作用。在这种情况下，三种Zn
• Synthesis and characterization of the zinc(ii)-fluorophore, 5-dimethylaminonaphthalene-1-sulfonic acid [2-(1,5,9-triazacyclododec-1-yl)ethyl]amide and its zinc(ii) complex
  作者：Tohru Koike、Tomoko Abe、Makoto Takahashi、Kazuhiro Ohtani、Eiichi Kimura、Motoo Shiro

  DOI：10.1039/b110878f

  日期：2002.4.9

  A new zinc(II)-fluorophore, 5-dimethylaminonaphthalene-1-sulfonic acid [2-(1,5,9-triazacyclododec-1-yl)ethyl]amide (HL) has been synthesized and characterized. The spectrophotometric and potentiometric pH-titration study disclosed a 1 ∶ 1 zinc(II) complexation with a stability constant, K(ZnL) of 101.3 (= [ZnL]aH+/[Zn2+][HL]) at 25 °C with I = 0.10 (NaCl) in aqueous solution, where L is the dansylamide deprotonated ligand. The fluorescence intensity of ZnL at 538 nm (excitation at 320 nm) is 5.2 times greater than that of the ligand (HL·H+ form) in aqueous solution at pH 7.8 and 25 °C with I = 0.10 (NaCl). The X-ray crystal analysis of the zinc(II) complex [ZnL(ClO4)·EtOH] showed a four-coordinate zinc(II) with three nitrogen atoms of the macrocyclic triamine and the dansylamide N− anion.

  合成并表征了一种新的锌(II)-荧光团5-二甲氨基萘-1-磺酸[2-(1,5,9-三氮杂环十二碳-1-基)乙基]酰胺(HL)。分光光度法和电位 pH 滴定研究表明，在 25 °C 下，与 I 形成 1 ∶ 1 锌 (II) 络合，稳定常数 K(ZnL) 为 101.3 (= [ZnL]aH+/[Zn2+][HL]) = 0.10 (NaCl) 在水溶液中，其中 L 是丹磺酰胺去质子化配体。在 pH 7.8、25 °C 的水溶液中，ZnL 在 538 nm（激发波长 320 nm）处的荧光强度是配体（HL·H+ 形式）的 5.2 倍。 = 0.10（氯化钠）。锌(II)络合物[ZnL(ClO4)·EtOH]的X射线晶体分析表明，锌(II)是具有大环三胺的三个氮原子的四配位锌(II)， 丹磺酰胺 N− 阴离子。
• Catalysis of Diribonucleoside Monophosphate Cleavage by Water Soluble Copper(II) Complexes of Calix[4]arene Based Nitrogen Ligands
  作者：Roberta Cacciapaglia、Alessandro Casnati、Luigi Mandolini、David N. Reinhoudt、Riccardo Salvio、Andrea Sartori、Rocco Ungaro

  DOI：10.1021/ja0632106

  日期：2006.9.1

  Calix[4]arenes functionalized at the 1,2-, 1,3-, and 1,2,3-positions of the upper rim with [12]ane-N-3 ligating units were synthesized, and their bi-and trimetallic zinc(II) and copper( II) complexes were investigated as catalysts in the cleavage of phosphodiesters as RNA models. The results of comparative kinetic studies using monometallic controls indicate that the subunits of all of the zinc(II) complexes and of the 1,3-distal bimetallic copper(II) complex 7-Cu-2 act as essentially independent monometallic catalysts. The lack of cooperation between metal ions in the above complexes is in marked contrast with the behavior of the 1,2-vicinal bimetallic copper(II) complex 6-Cu-2, which exhibits high catalytic efficiency and high levels of cooperation between metal ions in the cleavage of HPNP and of diribonucleoside monophosphates NpN'. A third ligated metal ion at the upper rim does not enhance the catalytic efficiency, which excludes the simultaneous cooperation in the catalysis of the three metal ions in 8-Cu-3. Rate accelerations relative to the background brought about by 6-Cu-2 and 8-Cu-3 (1.0 mM catalyst, water solution, pH 7.0, 50 degrees C) are on the order of 10(4)-fold, largely independent of the nucleobase structure, with the exception of the cleavage of diribonucleoside monophosphates in which the nucleobase N is uracil, namely UpU and UpG, for which rate enhancements rise to 10(5)-fold. The rationale for the observed selectivity is discussed in terms of deprotonation of the uracil moiety under the reaction conditions and complexation of the resulting anion with one of the copper(II) centers.