(Z)-3-((S)-1-Naphthalen-1-yl-ethylcarbamoyl)-acrylic acid | 176315-05-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-3-((S)-1-Naphthalen-1-yl-ethylcarbamoyl)-acrylic acid
• 英文别名: (Z)-4-[[(1S)-1-naphthalen-1-ylethyl]amino]-4-oxobut-2-enoic acid
• CAS: 176315-05-2
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: GXCHUCYDXROWNE-JUDLJHIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-((S)-1-Naphthalen-1-yl-ethylcarbamoyl)-acrylic acid 在 sodium acetate 、 乙酸酐 、 (S,S)-trans-2,5-bis(hydroxymethyl)pyrrolidine 作用下， 反应 50.0h， 生成
  参考文献：
  名称：

  Asymmetric cycloaddition of anthrone with N-substituted maleimides with C2-chiral pyrrolidines

  摘要：

  Base-catalyzed asymmetric cycloaddition of anthrone with achiral and chiral N-substituted maleimides was carried out in the presence of C-2-chiral pyrrolidines in almost quantitative yields. Chiral, non-racemic [4+2] adducts up to 61% ee were produced with achiral N-methyl and N-benzylmaleimide using the chiral catalysts. De's of the adducts up to 38% were observed in the cases of chiral N-substituted maleimides and achiral pyrrolidine, in which the absolute configuration of the major product was established by X-ray analysis. The combination of chiral maleimides and chiral catalysts afforded the adducts having up to 80% de. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(96)00473-9
• 作为产物：
  描述：

  马来酸酐 、 (S)-(-)-1-(1-萘基)乙胺 以 乙醚 为溶剂， 生成 (Z)-3-((S)-1-Naphthalen-1-yl-ethylcarbamoyl)-acrylic acid
  参考文献：
  名称：

  探测酶的立体特异性。手性胺和氨基醇衍生物对α-胰凝乳蛋白酶和枯草杆菌蛋白酶Carlsberg的抑制作用

  摘要：

  已经评估了各种对映体胺和氨基醇酰胺以及α-酮酰胺衍生物作为代表性丝氨酸蛋白酶α-胰凝乳蛋白酶（CT）和枯草杆菌蛋白酶Carlsberg（SC）的竞争性抑制剂。研究的每种化合物都是两种酶的有效竞争抑制剂。然而，仅对于最佳抑制剂，N-丙酮酰-1-（1-萘基）乙胺（对于CT的S-对映异构体，K 1 27μM）是值得注意的对映异构体区别，其中S-对映异构体明显更有效CT和SC的抑制剂比R-分别对应12.6和73倍的因子。通过分子模型分析揭示了负责这种强结合和对映异构的酶-抑制剂相互作用。

  DOI：

  10.1016/0040-4020(96)00078-6

文献信息

• Probing enzyme stereospecificity. Inhibition of α-chymotrypsin and subtilisin Carlsberg by chiral amine- and aminoalcohol-derivatives
  作者：Ernesto Occhiato、J. Bryan Jones

  DOI：10.1016/0040-4020(96)00078-6

  日期：1996.3

  and aminoalcohol amide and α-ketoamide derivatives have been evaluated as competitive inhibitors of the representative serine proteases α-chymotrypsin (CT) and subtilisin Carlsberg (SC). Each compound studied was an effective competitive inhibitor of both enzymes. However, only for the best inhibitor, N-pyruvoyl-1-(1-naphthyl)ethylamine (K1 27 μM for the S-enantiomer with CT), was noteworthy enantiomeric

  已经评估了各种对映体胺和氨基醇酰胺以及α-酮酰胺衍生物作为代表性丝氨酸蛋白酶α-胰凝乳蛋白酶（CT）和枯草杆菌蛋白酶Carlsberg（SC）的竞争性抑制剂。研究的每种化合物都是两种酶的有效竞争抑制剂。然而，仅对于最佳抑制剂，N-丙酮酰-1-（1-萘基）乙胺（对于CT的S-对映异构体，K 1 27μM）是值得注意的对映异构体区别，其中S-对映异构体明显更有效CT和SC的抑制剂比R-分别对应12.6和73倍的因子。通过分子模型分析揭示了负责这种强结合和对映异构的酶-抑制剂相互作用。
• Asymmetric cycloaddition of anthrone with N-substituted maleimides with C2-chiral pyrrolidines
  作者：Kyohei Tokioka、Satoshi Masuda、Tomomi Fujii、Yasuo Hata、Yukio Yamamoto

  DOI：10.1016/s0957-4166(96)00473-9

  日期：1997.1

  Base-catalyzed asymmetric cycloaddition of anthrone with achiral and chiral N-substituted maleimides was carried out in the presence of C-2-chiral pyrrolidines in almost quantitative yields. Chiral, non-racemic [4+2] adducts up to 61% ee were produced with achiral N-methyl and N-benzylmaleimide using the chiral catalysts. De's of the adducts up to 38% were observed in the cases of chiral N-substituted maleimides and achiral pyrrolidine, in which the absolute configuration of the major product was established by X-ray analysis. The combination of chiral maleimides and chiral catalysts afforded the adducts having up to 80% de. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.