(S)-tert-butyl 4-(methoxy(methyl)amino)-4-oxo-1-phenylbutan-2-ylcarbamate | 210533-63-4

• 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: (S)-tert-butyl 4-(methoxy(methyl)amino)-4-oxo-1-phenylbutan-2-ylcarbamate
• 英文别名: tert-butyl N-[(2S)-4-[methoxy(methyl)amino]-4-oxo-1-phenylbutan-2-yl]carbamate
• CAS: 210533-63-4
• 化学式: C₁₇H₂₆N₂O₄
• 分子量: 322.404
• InChiKey: BMCGAOJVGPWKDU-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 4-(methoxy(methyl)amino)-4-oxo-1-phenylbutan-2-ylcarbamate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 3-[(tert-butoxycarbonyl)amino]-4-phenylbutanaldehyde
  参考文献：
  名称：

  骨干修饰的短杂种δ-肽的发散超分子凝胶化。

  摘要：

  由于它们在生物学和材料科学中的广泛应用，短肽的有序超分子组装近来获得了发展势头。与α-肽相反，骨架修饰的肽仅获得了有限的成功。可以探索由β-，γ-和δ-氨基酸组成的主链修饰肽的蛋白水解稳定性和构象柔韧性，以设计有序的超分子凝胶和自组装材料。在本文中，我们报道了由一类新的短杂交二肽发散的超分子凝胶，该短二肽由构象灵活的新β（O）-δ5-氨基酸组成。由β3-和β（O）-δ5-Phe组成的杂二肽显示出由芳族溶剂形成的透明凝胶，而由β（O）-δ5-Phe组成的二肽在磷酸盐缓冲盐水（PBS）中显示出触变性凝胶。相反，从由交替的α-和β（O）-δ5-Phe以及γ4和β（O）-δ5-Phe组成的二肽中未观察到有机或水凝胶。进一步探索了β3，β（O）-δ5-苯丙氨酸二肽所表现出的有机胶凝特性，以从油水混合物中回收溢油。由β（O）-δ5，β（O）-δ5-Phe二肽显示的触变水凝胶与细胞培养基一起进一步用作基

  DOI：

  10.1021/acs.biomac.8b01684
• 作为产物：
  描述：

  Boc-Phe-O-COO-isoBu 在 silver benzoate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 10.0h， 生成 (S)-tert-butyl 4-(methoxy(methyl)amino)-4-oxo-1-phenylbutan-2-ylcarbamate
  参考文献：
  名称：

  Direct synthesis of N-protected β-amino dimethylhydroxamates: Application to the solid-phase synthesis of a peptide incorporating a new amide bond surrogate Ψ[CH2CH2NH]

  摘要：

  A rapid and efficient one-step synthesis of N-protected beta-amino dimethylhydroxamates starting from diazo ketones is reported A Fmoc-protected beta-amino aldehyde obtained by reduction of its corresponding dimethylhydroxamate was incorporated during solid phase assembly of an antigenic peptide. The resulting pseudopeptide containing an ethylene amino bond Psi[CH2CH2NH] was efficiently recovered. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00675-3

文献信息

• Synthesis and γ-secretase activity of APP substrate-based hydroxyethylene dipeptide isosteres
  作者：Alan Nadin、Andrew P. Owens、José L. Castro、Timothy Harrison、Mark S. Shearman

  DOI：10.1016/s0960-894x(02)00840-5

  日期：2003.1

  Two new APP substrate-based hydroxyethylene isosteres (AT and VI) were prepared and their dipeptide conjugates shown not to inhibit the gamma-secretase-mediated formation of either Abeta1-40 or Abeta1-42. The FG isostere and a des-hydroxy hydroxyethylene isostere also gave inactive compounds. Conversely, a number of compounds containing the intact substrate-unrelated Phe-Phe (FF) hydroxyethylene isostere

  制备了两个新的基于APP底物的羟乙烯等聚体（AT和VI），显示它们的二肽共轭物不抑制γ-分泌酶介导的Abeta1-40或Abeta1-42的形成。FG等排物和脱羟基羟乙烯等排物也得到非活性化合物。相反，许多含有完整的底物无关的Phe-Phe（FF）羟乙烯等排物的化合物被证明是有效的抑制剂（ED（50）= 14-732 nM）。这些结果表明，控制γ-分泌酶抑制剂基于底物设计的因素比最初想像的要复杂。
• Synthesis of 6- and 7-Membered Cyclic Enaminones: Scope and Mechanism
  作者：Micah J. Niphakis、Brandon J. Turunen、Gunda I. Georg

  DOI：10.1021/jo100907u

  日期：2010.10.15

  Six- and seven-membered cyclic enaminones can be prepared using common. environmentally benign reagents. Ammo acids are used as synthetic precursors allowing diversification and the incorporation of chirality The key reaction in this multistep process involves deprotection Boc-amino ynones and subsequent treatment with methanolic K2CO3 to induce cyclization. A beta-amino elimination side reaction was identified in a few labile substrates that led to loss of stereochemical purity of degradation. This process can be mitigated in specific cases using mild deprotection conditions NMR and deuteitum-labeling experiments provided valuable insight into the work kings and limitations of this reaction Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond-making and bond-breaking. thus changing die mode of addition to a 6-endo-trig cyclization This method can be used to construct an array of monocyclic and bicyclic scaffolds. many of which me found in well-known natural products (e g indolizidine, quinolizidine, and Stemona alkaloids).
• Amino Acid-Derived Enaminones:  A Study in Ring Formation Providing Valuable Asymmetric Synthons
  作者：Brandon J. Turunen、Gunda I. Georg

  DOI：10.1021/ja0609046

  日期：2006.7.1

  A new reaction for the preparation of enaminones has been discovered. This method employs beta-amino acids as starting materials to allow diversification as well as incorporation of chirality. The beta-amino acids, once converted to ynones, are readily cyclized to the desired six-membered enaminone via a two-step, one-pot protocol. Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond making and bond breaking, thus changing the mode of addition.
• Direct synthesis of N-protected β-amino dimethylhydroxamates: Application to the solid-phase synthesis of a peptide incorporating a new amide bond surrogate Ψ[CH2CH2NH]
  作者：David Limal、Anne Quesnel、Jean-Paul Briand

  DOI：10.1016/s0040-4039(98)00675-3

  日期：1998.6

  A rapid and efficient one-step synthesis of N-protected beta-amino dimethylhydroxamates starting from diazo ketones is reported A Fmoc-protected beta-amino aldehyde obtained by reduction of its corresponding dimethylhydroxamate was incorporated during solid phase assembly of an antigenic peptide. The resulting pseudopeptide containing an ethylene amino bond Psi[CH2CH2NH] was efficiently recovered. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Divergent Supramolecular Gelation of Backbone Modified Short Hybrid δ-Peptides
  作者：Rahi M. Reja、Rajat Patel、Vivek Kumar、Anjali Jha、Hosahudya N. Gopi

  DOI：10.1021/acs.biomac.8b01684

  日期：2019.3.11

  success has been achieved from the backbone modified peptides. The proteolytic stability and conformational flexibility of the backbone modified peptides composed of β-, γ-, and δ-amino acids can be explored to design ordered supramolecular gels and self-assembled materials. In this article, we are reporting the divergent supramolecular gels from a new class of short hybrid dipeptides composed of conformationally

  由于它们在生物学和材料科学中的广泛应用，短肽的有序超分子组装近来获得了发展势头。与α-肽相反，骨架修饰的肽仅获得了有限的成功。可以探索由β-，γ-和δ-氨基酸组成的主链修饰肽的蛋白水解稳定性和构象柔韧性，以设计有序的超分子凝胶和自组装材料。在本文中，我们报道了由一类新的短杂交二肽发散的超分子凝胶，该短二肽由构象灵活的新β（O）-δ5-氨基酸组成。由β3-和β（O）-δ5-Phe组成的杂二肽显示出由芳族溶剂形成的透明凝胶，而由β（O）-δ5-Phe组成的二肽在磷酸盐缓冲盐水（PBS）中显示出触变性凝胶。相反，从由交替的α-和β（O）-δ5-Phe以及γ4和β（O）-δ5-Phe组成的二肽中未观察到有机或水凝胶。进一步探索了β3，β（O）-δ5-苯丙氨酸二肽所表现出的有机胶凝特性，以从油水混合物中回收溢油。由β（O）-δ5，β（O）-δ5-Phe二肽显示的触变水凝胶与细胞培养基一起进一步用作基