N,N-di(tert-butoxycarbonyl)-5-amino-1-pentanal | 177899-22-8

• 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-di(tert-butoxycarbonyl)-5-amino-1-pentanal
• 英文别名: Imidodicarbonic acid, 2-(5-oxopentyl)-, 1,3-bis(1,1-dimethylethyl) ester；tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]-N-(5-oxopentyl)carbamate
• CAS: 177899-22-8
• 化学式: C₁₅H₂₇NO₅
• 分子量: 301.383
• InChiKey: OQKYKSTUUZERJP-UHFFFAOYSA-N

物化性质

• 沸点：
  368.8±44.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-di(tert-butoxycarbonyl)-5-amino-1-pentanal 在 哌啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyl N-[(E)-6-(benzenesulfonyl)-4-hydroxyhex-5-enyl]carbamate
  参考文献：
  名称：

  De Vicente, Lavier; Arrayas, Ramön Gömez; Canada, Lavier, Synlett, 2000, # 1, p. 53 - 56

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(N-叔丁氧羰基氨基)-1-戊醇 在 咪唑 、 正丁基锂 、 四丁基氟化铵 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 N,N-di(tert-butoxycarbonyl)-5-amino-1-pentanal
  参考文献：
  名称：

  通过γ-氧化的α，β-不饱和砜环化的立体选择性合成羟基吡咯烷和羟基哌啶

  摘要：

  顺式和反式2，3-二取代的吡咯烷和哌啶已通过分子内共轭添加N-取代的γ-氧化的-α，β-不饱和苯基砜而立体制备。从醇获得最佳的顺式选择性，从OTIPS衍生物获得最佳的反式选择性。

  DOI：

  10.1016/0040-4039(96)00551-5

文献信息

• Stereoselective synthesis of hydroxypyrrolidines and hydroxypiperidines by cyclization of γ-oxygenated-α,β-unsaturated sulfones
  作者：Juan Carlos Carretero、Ramón Gómez Arrayás、Isabel Storch de Gracia

  DOI：10.1016/0040-4039(96)00551-5

  日期：1996.5

  cis and trans 2,3-disubstituted pyrrolidines and piperidines have been prepared stereoselectively by intramolecular conjugate addition of N-substituted γ-oxygenated-α,β-unsaturated phenyl sulfones. The best cis-selectivities were obtained from the alcohols and the best trans-selectivities from the OTIPS derivatives.

  顺式和反式2，3-二取代的吡咯烷和哌啶已通过分子内共轭添加N-取代的γ-氧化的-α，β-不饱和苯基砜而立体制备。从醇获得最佳的顺式选择性，从OTIPS衍生物获得最佳的反式选择性。
• De-novo designed β-lysine derivatives can both augment and diminish the proliferation rates of E. coli through the action of Elongation Factor P
  作者：Ciara M. McDonnell、Magda Ghanim、J. Mike Southern、Vincent P. Kelly、Stephen J. Connon

  DOI：10.1016/j.bmcl.2022.128545

  日期：2022.3

  An investigation into the effect of modified β-lysines on the growth rates of eubacterial cells is reported. It is shown that the effects observed are due to the post translational modification of Elongation Factor P (EFP) with these compounds catalysed by PoxA. PoxA was found to be remarkably promiscuous, which allowed the activity of a wide range of exogenous β-lysines to be examined. Two chain-elongated

  报道了一项研究修饰的β-赖氨酸对真细菌细胞生长速率的影响。结果表明，观察到的效果是由于用 PoxA 催化的这些化合物对延伸因子 P (EFP) 进行了翻译后修饰。PoxA 被发现是非常混杂的，这使得可以检查广泛的外源 β-赖氨酸的活性。两种在氨基烷基链长度上仅相差 2 个碳单位的链延长的 β-赖氨酸衍生物表现出相反的生物活性——一种促进生长，另一种延缓生长。两种化合物均显示通过 EFP 的修饰起作用。
• Design, synthesis, and biological evaluation of cytotoxic 11-aminoalkenylindenoisoquinoline and 11-diaminoalkenylindenoisoquinoline topoisomerase I inhibitors
  作者：Xiangshu Xiao、Smitha Antony、Glenda Kohlhagen、Yves Pommier、Mark Cushman

  DOI：10.1016/j.bmc.2004.07.027

  日期：2004.10

  The cytotoxic indenoisoquinolines are a novel class of noncamptothecin topoisomerase I inhibitors having certain features that compare favorably with the camptothecins. A new strategy was adopted to attach aminoalkenyl substituents at C-11 of the indenoisoquinoline ring system, which, according to molecular modeling, would orient the side chains toward the DNA minor groove. All of the newly synthesized compounds were more cytotoxic than the parent indenoisoquinoline NSC 314622. Despite an imperfect correlation between cytotoxicities and topoisomerase I inhibition results, the hypothetical structural model of the cleavage complex presented here provides a conceptual framework to explain the structure-activity relationships. (C) 2004 Elsevier Ltd. All rights reserved.
• Palladium-catalyzed synthesis of tryptamines and tryptamine homologues: synthesis of psilocin
  作者：Chunmei Hu、Hua Qin、Yuxin Cui、Yanxing Jia

  DOI：10.1016/j.tet.2009.09.050

  日期：2009.11

  A new Pd-catalyzed method for the synthesis of tryptamines is developed, and its applications to the synthesis of Corey's aspidophytine tryptamine 15 and psilocin 20 are also described. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism
  作者：Markus Baumann、Lina Marie Nome、Zack G. Zachariassen、Stefanie Karlshøj、Torgils Fossen、Mette M. Rosenkilde、Jon Våbenø、Bengt Erik Haug

  DOI：10.1016/j.tet.2017.05.057

  日期：2017.7

  preparation of a new 2,6,8-trisubstituted bicyclic tripeptidomimetic scaffold through TFA-mediated cyclization of a linear precursor containing three side chains. The introduction of a triphenylmethyl-protected thiol into carboxylic acid containing building blocks through sulfa Michael additions onto α,β-unsaturated hexafluoroisopropyl esters is described. The stereoselectivity of the bicycle formation was found

  我们在这里报告通过TFA介导的包含三个侧链的线性前体的环化，制备新的2,6,8-三取代双环三肽模拟支架。描述了通过在α，β-不饱和六氟异丙基酯上的磺胺迈克尔加成将三苯甲基保护的硫醇引入到含羧酸的结构单元中。发现自行车结构的立体选择性略低于先前报道的类似的3,6,8-三取代支架的立体选择性。此外，当R 1时，线性前体的构型以不同的方式指导环化的立体化学结果侧链位于自行车的C2（当前工作）而不是C3（先前的工作）上。合成了基于新支架的三肽模拟化合物，并评估了其对CXCR4的拮抗力，其中一种化合物（45a）的活性与早期报道的3,6,8三肽模拟自行车相似。