N,N'-bis(N-Cbz-L-valinyl)-1,6-diaminohexane | 106407-83-4

• 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: N,N'-bis(N-Cbz-L-valinyl)-1,6-diaminohexane
• 英文别名: N,N'-Bis-(N-benzyloxycarbonyl-L-valyl)-hexamethylendiamin；benzyl N-[(2S)-3-methyl-1-[6-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]hexylamino]-1-oxobutan-2-yl]carbamate
• CAS: 106407-83-4
• 化学式: C₃₂H₄₆N₄O₆
• 分子量: 582.74
• InChiKey: GFANDROCUWMWBP-NSOVKSMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  42
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(N-Cbz-L-valinyl)-1,6-diaminohexane 在 氢溴酸 、 溶剂黄146 、 sodium hydroxide 作用下， 生成 (S)-2-Amino-N-[6-((S)-2-amino-3-methyl-butyrylamino)-hexyl]-3-methyl-butyramide
  参考文献：
  名称：

  新的手性四氮杂配体，用于将二烷基锌有效地对映选择性加成到芳族醛中

  摘要：

  研究了一系列手性四氮杂配体，用于将二烷基锌对映体选择性加成到醛中。这些双（氨基酰胺）配体在将有机锌添加到芳族醛中时显示出高对映选择性。配体上的不同结构元素似乎在确定观察到的对映选择性中起重要作用。配体4b（N，N'-双（N -1-戊基）-1,3-二氨基丙烷，带有带有3C原子的脂族间隔基）催化Et 2的添加锌转化为苯甲醛，1-萘醛，4-甲氧基苯甲醛和4-氯苯甲醛，得到相应的醇产物，其转化率和选择性极好，对映选择性分别为99％，97％，98％和82％。DFT计算提供了对映过程的机理的理解。

  DOI：

  10.1016/j.tet.2008.07.099
• 作为产物：
  描述：

  CBZ-L-缬氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 27.0h， 生成 N,N'-bis(N-Cbz-L-valinyl)-1,6-diaminohexane
  参考文献：
  名称：

  U-Turn 预组织肽模拟物的有效大环化：分子内氢键和疏溶剂效应的作用

  摘要：

  源自氨基酸的简单拟肽分子在乙腈中与间位和对位双（溴甲基）苯反应，非常有效地产生大环结构。环化反应不需要高稀释技术，并且似乎对形成的大环的大小不敏感。通过 (1)H NMR、单晶 X 射线衍射、荧光测量和分子力学获得的数据分析表明，折叠构象可以预先组织系统以实现有效的环化。分析了在折叠构象存在下分子内氢键和疏溶剂效应所起的作用。

  DOI：

  10.1021/ja0284759

文献信息

• New chiral tetraaza ligands for the efficient enantioselective addition of dialkylzinc to aromatic aldehydes
  作者：M. Isabel Burguete、Jorge Escorihuela、Santiago V. Luis、Agustí Lledós、Gregori Ujaque

  DOI：10.1016/j.tet.2008.07.099

  日期：2008.10

  enantioselective addition of dialkylzinc to aldehydes. These bis(amino amide) ligands show high enantioselectivity in the addition of organozincs to aromatic aldehydes. Different structural elements on the ligands seem to play an important role in determining the observed enantioselectivity. Ligand 4b (N,N′-bis(N-l-valinyl)-1,3-diaminopropane, with an aliphatic spacer with 3C atoms) catalyzed the addition of Et2Zn

  研究了一系列手性四氮杂配体，用于将二烷基锌对映体选择性加成到醛中。这些双（氨基酰胺）配体在将有机锌添加到芳族醛中时显示出高对映选择性。配体上的不同结构元素似乎在确定观察到的对映选择性中起重要作用。配体4b（N，N'-双（N -1-戊基）-1,3-二氨基丙烷，带有带有3C原子的脂族间隔基）催化Et 2的添加锌转化为苯甲醛，1-萘醛，4-甲氧基苯甲醛和4-氯苯甲醛，得到相应的醇产物，其转化率和选择性极好，对映选择性分别为99％，97％，98％和82％。DFT计算提供了对映过程的机理的理解。
• Fabrication of helical hybrid silica bundles
  作者：Yonggang Yang、Miho Nakazawa、Masahiro Suzuki、Hirofusa Shirai、Kenji Hanabusa

  DOI：10.1039/b700615b

  日期：——

  A series of C2-symmetric bridged silsesquioxanes derived from L- and D-valine have been designed and synthesized. They were capable of forming physical gels in organic solvents such as ethanol, THF, and 1,4-dioxane. These silsesquioxanes formed helical bundles in 1,4-dioxane. With respect to the helical sense, a clear odd–even effect was found in the carbon number of the central alkylene segment. The silsesquioxanes with odd number alkylene segments derived from L-valine tended to self-assemble into right-handed helical bundles. On the contrary, those with even number alkylene segments tended to form left-handed helical bundles. Moreover, enantiomers derived from D-valine showed the opposite helical sense. The p : d ratio played an important role in the determination of helical sense. After sol–gel polycondensation under catalysts such as HCl, NaOH, and TBAF, helical hybrid silica bundles were identified in FESEM images. The helical sense of the bundles was sensitive to the catalysts and reaction conditions. Hybrid silica sponges showing both superoleophilic and superhydrophobic properties were obtained under a HCl diffusion procedure.

  一系列源自L-和D-缬氨酸的C2对称桥接硅烷氧烷已被设计和合成。这些化合物能够在乙醇、四氢呋喃和1,4-二氧烷等有机溶剂中形成物理凝胶。这些硅烷氧烷在1,4-二氧烷中形成螺旋束。在螺旋方向上，发现中央烷基段的碳原子数存在明显的奇偶效应。源自L-缬氨酸的奇数烷基段硅烷氧烷倾向于自组装成右手螺旋束。相反，偶数烷基段的则倾向于形成左手螺旋束。此外，源自D-缬氨酸的对映体表现出相反的螺旋方向。p : d 比例在确定螺旋方向上发挥了重要作用。在HCl、NaOH和TBAF等催化剂的作用下，经过溶胶-凝胶聚缩合后，通过FESEM图像可以识别出螺旋混合硅氧化物束。这些束的螺旋方向对催化剂和反应条件敏感。在HCl扩散过程中获得了显示超级亲油和超级疏水特性的混合硅海绵。
• Synthetic Macrocyclic Peptidomimetics as Tunable pH Probes for the Fluorescence Imaging of Acidic Organelles in Live Cells
  作者：Francisco Galindo、M. Isabel Burguete、Laura Vigara、Santiago V. Luis、Nurul Kabir、Jelena Gavrilovic、David A. Russell

  DOI：10.1002/anie.200501920

  日期：2005.10.14
• Coordination of Cu²⁺ Ions to <i>C</i>₂ Symmetric Pseudopeptides Derived from Valine
  作者：Salvador Blasco、M. Isabel Burguete、M. Paz Clares、Enrique García-España、Jorge Escorihuela、Santiago V. Luis

  DOI：10.1021/ic100748g

  日期：2010.9.6

  The acid base and coordination properties of a family of pseudopeptidic ligands with C-2 symmetry derived from valine (4a-e) have been studied using a variety of techniques as a model for metal coordination in peptides and proteins. The Cu2+ cation has been selected for coordination studies, although, for comparison, some results for Zn2+ are also presented. Good agreement has been obtained between the results obtained by potentiometric titrations, spectroscopic analysis, and mass spectrometry (ESI) studies. These results highlight the potential for the use of ESI MS for characterizing the nature of the complex species formed. Clearly, the Cu2+ complexes are much more stable than the Zn2+ complexes. While the role of the aliphatic spacer seems to be very minor in the case of the Zn2+ complexes, revealing the ability of this cation to accommodate different coordination environments, this role is critical in the case of Cu2+. Different complexes with 1:1 or 2:2 Cu2+;L stoichiometries can be formed according to the length of the spacer and the basicity of the media. This is fully illustrated by the resolution of the X-ray structures of two different Cu2+ complexes corresponding to the ligands containing a spacer with two methylene groups (ligand 4a, complex 6a [Cu-2(H_L-1)(2)](ClO4)(2) with a 2:2 stoichiometry) and a propylene spacer (4b, complex 5b [CuH_L-2)center dot CH3CH2OH with a 1:1 stoichiometry).
• Schroeder,E. et al., Justus Liebigs Annalen der Chemie, 1961, vol. 646, p. 101 - 118
  作者：Schroeder,E. et al.

  DOI：——

  日期：——