(S) tert-butyl 3-methyl-1-(naphthalen-1-ylamino)-1-oxobutan-2-ylcarbamate | 870533-25-8

• 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: (S) tert-butyl 3-methyl-1-(naphthalen-1-ylamino)-1-oxobutan-2-ylcarbamate
• CAS: 870533-25-8
• 化学式: C₂₀H₂₆N₂O₃
• 分子量: 342.438
• InChiKey: KUSPWAAFFLNPTO-KRWDZBQOSA-N

物化性质

• 熔点：
  145-146 °C
• 沸点：
  545.9±33.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.43
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S) tert-butyl 3-methyl-1-(naphthalen-1-ylamino)-1-oxobutan-2-ylcarbamate 在 盐酸 、 sodium tetrahydroborate 、 magnesium sulfate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 41.0h， 生成 (S)-2-((2-hydroxybenzyl)amino)-3-methyl-N-(naphthalen-1-yl)butanamide
  参考文献：
  名称：

  通过开环-不对称重合羟基内酰胺开发基于亚甲基内酰胺的N，O-螺环化合物的新催化对映选择性形成

  摘要：

  开发了基于亚甲基内酰胺的N，O-螺环化合物的催化对映选择性形成。由N-羰基邻苯二甲酰亚胺和β-氨基官能化的烯丙基硼酸酯制备的羟基内酰胺在催化量的MgBr 2和手性氨基苯酚存在下进行开环-不对称重合反应，从而以优异的收率和高对映选择性提供相应的N，O-螺环化合物。

  DOI：

  10.1016/j.tet.2020.131252
• 作为产物：
  描述：

  N-Boc-L-缬氨酸 、 1-萘肼 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S) tert-butyl 3-methyl-1-(naphthalen-1-ylamino)-1-oxobutan-2-ylcarbamate
  参考文献：
  名称：

  用于靛红与酮的对映选择性羟醛反应的简单伯氨基酰胺有机催化剂

  摘要：

  发现使用新设计的氨基酰胺有机催化剂，各种靛红与酮的对映选择性羟醛反应可提供手性 3-取代 3-羟基-2-羟吲哚，收率良好至极好，立体选择性（高达 99 %，高达 98 % ee，同步/反 = 99:1); 一种催化剂，3i，证明特别成功。所得羟吲哚中的一种，3-羟基-3-(2-氧代环己基)-2-吲哚酮可用作药学上重要化合物的合成中间体，并且就其本身而言，显示出有趣的抗惊厥活性。

  DOI：

  10.1002/ejoc.201600414

文献信息

• Isomeric chiral pyrrole diamides and their efficacy in enantioselective sensing of tartrate in sol–gel medium
  作者：Kumaresh Ghosh、Anupam Majumdar

  DOI：10.1016/j.tetlet.2016.06.128

  日期：2016.8

  synthesized for chiral recognition of hydroxycarboxylates in sol–gel medium. Of the two isomeric chiral receptors, receptor 1 shows selective sensing of d-tetrabutylammonium tartrate over its mirror image isomer in CH3CN. The isomeric receptor 2 did not show any enantioselectivity in the recognition. Moreover, the receptor 1 validates prompt visual sensing of d-tartrate through gelation. The recognition

  设计并合成了基于吡啶基序的手性吡咯二酰胺裂隙1和2，用于在溶胶-凝胶介质中手性识别羟基羧酸盐。在两个异构的手性受体中，受体1在其CH 3 CN中的镜像异构体上显示出酒石酸d-丁酯的选择性传感。异构体受体2在识别中没有显示任何对映选择性。此外，受体1通过凝胶验证了酒石酸d-酒石的迅速视觉感测。通过荧光，紫外可见，1 H NMR和CD光谱法研究了受体的识别特性。
• Amino Amide Organocatalysts for Asymmetric Michael Addition of β-Keto Esters with β-Nitroolefins
  作者：Isiaka Alade Owolabi、Madhu Chennapuram、Chigusa Seki、Yuko Okuyama、Eunsang Kwon、Koji Uwai、Michio Tokiwa、Mitsuhiro Takeshita、Hiroto Nakano

  DOI：10.1246/bcsj.20180302

  日期：2019.3.15

  Asymmetric Michael addition of β-keto esters with trans-β-nitroolefins using chiral amino amide organocatalyst was tried and afforded synthetically useful chiral Michael adducts in both excellent c...

  使用手性氨基酰胺有机催化剂尝试了β-酮酯与反式-β-硝基烯烃的不对称迈克尔加成，并以两种优异的方式提供了合成有用的手性迈克尔加合物。
• Inhibitory effect of novel somatostatin peptide analogues on human cancer cell growth based on the selective inhibition of DNA polymerase β
  作者：Isoko Kuriyama、Anna Miyazaki、Yuko Tsuda、Hiromi Yoshida、Yoshiyuki Mizushina

  DOI：10.1016/j.bmc.2012.11.024

  日期：2013.1

  The present study was designed to investigate the anticancer activity of novel nine small peptides (compounds 1-9) derived from TT-232, a somatostatin structural analogue, by analyzing the inhibition of mammalian DNA polymerase (pol) and human cancer cell growth. Among the compounds tested, compounds 3 [tert-butyloxycarbonyl (Boc)-Tyr-Phe-1-naphthylamide], 4 (Boc-Tyr-Ile-1-naphthylamide), 5 (Boc-Tyr-Leu-1-naphthylamide) and 6 (Boc-Tyr-Val-1-naphthylamide) containing tyrosine (Tyr) but no carboxyl groups, selectively inhibited the activity of rat pol beta, which is a DNA repair-related pol. Compounds 3-6 strongly inhibited the growth of human colon carcinoma HCT116 p53(+/+) cells. The influence of compounds 1-9 on HCT116 p53(+/+) cell growth was similar to that observed for HCT116 p53(+/+) cells. These results suggest that the cancer cell growth suppression induced by these compounds might be related to their inhibition of pol. Compound 4 was the strongest inhibitor of pol beta and cancer cell growth among the nine compounds tested. This compound specifically inhibited rat pol beta activity, but had no effect on the other 10 mammalian pols investigated. Compound 4 combined with methyl methane sulfonate (MMS) treatment synergistically suppressed HCT116 p53(+/+) cell growth compared with MMS alone. This compound also induced apoptosis in HCT116 cells with or without p53. From these results, the influence of compound 4, a specific pol beta inhibitor, on the relationship between DNA repair and cancer cell growth is discussed. (C) 2012 Elsevier Ltd. All rights reserved.
• Pyrrole-based tetra-amide for hydrogen pyrophosphate (HP₂O₇³⁻) and F⁻ ions in sol-gel medium
  作者：Sumit Ghosh、Koushik Goswami、Kumaresh Ghosh

  DOI：10.1080/10610278.2017.1348603

  日期：2017.12.2

  A simple pyrrole-based tetra-amide 1 shows selective fluorescence sensing of HP2O73- over a series of other anions in CH3CN by exhibiting excimer emission at similar to 450nm. In DMSO:CHCl3 (1:5 v/v), compound 1 forms gel that undergoes disintegration to sol in the presence of basic anions such as F-, AcO- and H2PO4-. However, the gel state of 1 under a particular condition is observed to be selective to F- over AcO- and H2PO4- anions. The recognition properties of the receptor have been studied by fluorescence, UV-vis and H-1 NMR spectroscopic methods.