L-phenylalaninal dimethyl acetal | 55707-43-2

• 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: L-phenylalaninal dimethyl acetal
• 英文别名: (S)-1-benzyl-2,2-dimethoxyethylamine；(S)-1-benzyl-2,2-dimethoxyethan-1-amine；L-phenylalanine dimethyl acetal；(2S)-1,1-dimethoxy-3-phenylpropan-2-amine
• CAS: 55707-43-2
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: IFUOZMQFLICJQQ-JTQLQIEISA-N

物化性质

• 沸点：
  291.1±40.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-phenylalaninal dimethyl acetal 在 碘甲烷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 36.5h， 生成 (S)-1-benzyl-3-(1-benzyl-2,2-dimethoxyethyl)-1-dimethylaminourea
  参考文献：
  名称：

  Modular construction of quaternary hemiaminal-based inhibitor candidates and their in cellulo assessment with HIV-1 protease

  摘要：

  Non-peptidomimetic drug-like protease inhibitors have potential for circumventing drug resistance. We developed a much-improved synthetic route to our previously reported inhibitor candidate displaying an unusual quaternized hemi-aminal. This functional group forms from a linear precursor upon passage into physiological media. Seven variants were prepared and tested in cellulo with our HIV-1 fusion-protein technology that result in an eGFP-based fluorescent readout. Three candidates showed inhibition potency above 20 mu M and toxicity at higher concentrations, making them attractive targets for further refinement. Importantly, our class of original inhibitor candidates is not recognized by two major multidrug resistance pumps, quite in contrast to most clinically applied HIV-1 protease inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.018
• 作为产物：
  描述：

  (S)-1-benzyl-2,2-dimethoxyethylammonium N-acetyl-D-phenylalaninate 以 异丙醇 为溶剂， 反应 1.5h， 生成 L-phenylalaninal dimethyl acetal
  参考文献：
  名称：

  某些α-氨基缩醛的拆分和绝对构型：对映纯N保护的α-氨基醛

  摘要：

  据报道，通过与光学纯的N-保护的氨基酸形成非对映异构体盐，成功地分离了rac - α-氨基缩醛。α-氨基缩醛对映异构体的绝对构型分配是通过涉及N-保护的完全非消旋化学相关方法和新的有效水解步骤，然后还原所得的N-保护的α-氨基醛中间体进行的。举例说明了光学富集的α-氨基缩醛的消旋方法，以使两种对映异构体均价。

  DOI：

  10.1007/s00726-011-1117-6

文献信息

• Solid-phase synthesis of C-terminal peptide aldehydes from amino acetals anchored to a backbone amide linker (BAL) handle
  作者：Fanny Guillaumie、Joseph C Kappel、Nicholas M Kelly、George Barany、Knud J Jensen

  DOI：10.1016/s0040-4039(00)00950-3

  日期：2000.8

  Peptide aldehydes were synthesized, starting from amino acetals, by a solid-phase backbone amide linker (BAL) strategy.

  通过固相主链酰胺接头（BAL）策略从氨基缩醛开始合成肽醛。
• Diversity-Oriented Synthesis of a Drug-Like System Displaying the Distinctive N→C═O Interaction
  作者：Michael Waibel、Jens Hasserodt

  DOI：10.1021/jo800719j

  日期：2008.8.1

  describes the syntheses and characterization of two hydrazino ureas. These fold into a six-membered ring by virtue of the infrequently observed δ+N→C═Oδ− interaction when solvated by polar protic media. The highly polar functional group resulting from this interaction is hypothesized to especially reproduce electronic but also steric features of the transition states of peptide hydrolysis. The urea moiety

  这项研究描述了两种肼基脲的合成和表征。这些凭借很少观察到折叠成六元环δ+ Ñ→C = O δ-被极性质子质子介质溶解时发生相互作用。据推测，由这种相互作用产生的高极性官能团可特别重现肽水解过渡态的电子特征和空间特征。尿素部分构成了现代HIV-1蛋白酶（HIV PR）抑制剂的另一个关键要素，并且意在与酶瓣相互作用。我们已经开发出一种高效，聚合的对映纯化合物合成路线，该路线使用CDI偶联两个独立的构件，一个独立于氨基酸，另一个独立于易获得的肼。因此，为了筛选新的HIV PR抑制剂，需要快速产生多样性。7和8在甲醇中。传递至非极性介质后，观察到完全转化为线性醛形式。
• [EN] PROCESS OF PREPARATION OF OPTICALLY ACTIVE ALPHA AMINOACETALS<br/>[FR] PRÉPARATION D'ALPHA AMINOCÉTALS OPTIQUEMENT ACTIFS
  申请人：CLARIANT SPECIALTY FINE CHEM

  公开号：WO2009106386A1

  公开（公告）日：2009-09-03

  The invention relates to a process for preparing optically active α-aminoacetals by resolution of a racemic mixture or of a mixture of enantiomers via the formation of diastereoisomeric salts, and also novel intermediates in the form of diastereoisomeric salts.

  该发明涉及一种制备光学活性α-氨基缩醛的方法，通过分离外消旋混合物或对映异构体混合物，通过形成二对映异构盐，并且还涉及以二对映异构盐形式存在的新型中间体。
• Catalytic Diastereoselective Petasis Reactions
  作者：Giovanni Muncipinto、Philip N. Moquist、Stuart L. Schreiber、Scott E. Schaus

  DOI：10.1002/anie.201103271

  日期：2011.8.22

  Multicomponent Petasis reactions: The first diastereoselective Petasis reaction catalyzed by chiral biphenols that enables the synthesis of syn and anti β‐amino alcohols in pure form has been developed. The reaction exploits a multicomponent approach that involves boronates, α‐hydroxy aldehydes, and amines (see scheme).

  多组分 Petasis 反应：第一个由手性联苯酚催化的非对映选择性 Petasis 反应已经开发出来，该反应能够合成纯形式的顺式和反式 β-氨基醇。该反应采用多组分方法，涉及硼酸盐、α-羟基醛和胺（参见方案）。
• N-quaternary compounds—IXL
  作者：M. Gacek、K. Undheim

  DOI：10.1016/s0040-4020(01)97413-7

  日期：1974.1

  (S)-α-Trimethylammonio aldehydes have been synthesised over several steps from corresponding amino acids. The dichroic carbonyl absorption can be rationalised in terms of the Octant Rule with the assumption of a preferred conformation. The chiroptical properties of intermediate α-phthalimido aldehydes have also been investigated.

  （S）-α-三甲基氨醛已经从相应的氨基酸经过数步合成。假设优选构象，则可以根据Octant法则合理化二色性羰基吸收。还已经研究了中间α-邻苯二甲酰亚胺基醛的手性。