(S)-2-amino-N-(anthracene-1-yl)-3-phenylpropan-amide | 615580-71-7

• 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)-2-amino-N-(anthracene-1-yl)-3-phenylpropan-amide
• 英文别名: [(S)-2-amino-N-(anthracen-1-yl)-3-phenylpropanamide]*HBr；(2S)-2-amino-N-anthracen-1-yl-3-phenylpropanamide
• CAS: 615580-71-7
• 化学式: C₂₃H₂₀N₂O
• 分子量: 340.425
• InChiKey: IYGWEQDZEJYALU-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 (S)-2-amino-N-(anthracene-1-yl)-3-phenylpropan-amide 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以51%的产率得到(bis-[(S)-2-amino-N-(anthracen-1-yl)-3-phenylpropanamidato])copper(II)
  参考文献：
  名称：

  A turn-on fluorescent indicator for citrate with micromolar sensitivity

  摘要：

  一种用于柠檬酸（柠檬酸盐）的激发型荧光指示剂已被开发出来，其荧光发射增强度高（+1500%），且对其他羧酸盐的干扰较低。该传感器基于一种非发光性的铜(II)荧光氨基酸酰胺复合物，当加入柠檬酸盐时，该复合物会解离生成发光的配体。据估计，这一新型化学传感系统的检测限约为0.5 µM。与基于柠檬酸裂解酶的标准方法相比，这一新颖的柠檬酸盐分析方法的灵敏度大约是其102-103倍。

  DOI：

  10.1039/b711139h
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 N-羟基琥珀酰亚胺酯 在 氢溴酸 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (S)-2-amino-N-(anthracene-1-yl)-3-phenylpropan-amide
  参考文献：
  名称：

  Nickel complexes from α-amino amides as efficient catalysts for the enantioselective Et2Zn addition to benzaldehyde

  摘要：

  Ni2+ complexes derived from simple alpha-amino amides catalyze very efficiently the addition of Et2Zn to benzaldehyde, giving (S)-1-phenylethanol as the major isomer in most cases (94% yield, 97% ee for R=Bn). The nature of the substituent on the amide nitrogen atom seems to play a key role in determining the asymmetric induction observed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01705-2

文献信息

• Simple Primary Amino Amide Organocatalyst for Enantioselective Aldol Reactions of Isatins with Ketones
  作者：Jo Kimura、Ummareddy Venkata Subba Reddy、Yoshihito Kohari、Chigusa Seki、Yasuteru Mawatari、Koji Uwai、Yuko Okuyama、Eunsang Kwon、Michio Tokiwa、Mitsuhiro Takeshita、Tatsuo Iwasa、Hiroto Nakano

  DOI：10.1002/ejoc.201600414

  日期：2016.8

  Enantioselective aldol reactions of various isatins with ketones using newly designed amino amide organocatalysts were found to provide chiral 3-substituted 3-hydroxy-2-oxindoles in good to excellent yields and with excellent stereoselectivities (up to 99 %, up to 98 % ee, syn/anti = 99:1); one catalyst, 3i, proved particularly successful. One of the resulting oxindoles, 3-hydroxy-3-(2-oxocyclohexyl)-2-indolinone

  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。
• Enantioselective nickel-catalyzed conjugate addition of dialkylzinc to chalcones using chiral α-amino amides
  作者：Jorge Escorihuela、M. Isabel Burguete、Santiago V. Luis

  DOI：10.1016/j.tetlet.2008.09.120

  日期：2008.11

  A series of alpha-amino amides derived from natural amino acids (alanine, valine, phenylalanine, isoleucine, and phenylglycine) have been synthesized and fully characterized. Their Ni(II) complexes prepared from Ni(acac)(2) catalyze the enantioselective conjugate addition of diethylzinc to chalcones in high yields and in good enantioselectivities (up to 84%). The side chain of the amino acid and the substituents in the amide nitrogen govern the enantioselectivity of the catalytic process. (c) 2008 Elsevier Ltd. All rights reserved.
• A turn-on fluorescent indicator for citrate with micromolar sensitivity
  作者：M. Isabel Burguete、Francisco Galindo、Santiago V. Luis、Laura Vigara

  DOI：10.1039/b711139h

  日期：——

  A turn-on fluorescent indicator for citric acid (citrate) has been developed, displaying high emission enhancement (+1500%) and low interference by other carboxylates. The sensor is based on the non-emissive copper(II) complex of a fluorescent amino amide, which, upon addition of citrate decomplexates to yield the emissive ligand. The detection limit estimated for this new chemosensing system is about 0.5 µM. This novel approach to the analysis of citrate constitutes an alternative ca. 102–103 times more sensitive than the standard method based on the enzyme citrate lyase.

  一种用于柠檬酸（柠檬酸盐）的激发型荧光指示剂已被开发出来，其荧光发射增强度高（+1500%），且对其他羧酸盐的干扰较低。该传感器基于一种非发光性的铜(II)荧光氨基酸酰胺复合物，当加入柠檬酸盐时，该复合物会解离生成发光的配体。据估计，这一新型化学传感系统的检测限约为0.5 µM。与基于柠檬酸裂解酶的标准方法相比，这一新颖的柠檬酸盐分析方法的灵敏度大约是其102-103倍。
• Nickel complexes from α-amino amides as efficient catalysts for the enantioselective Et2Zn addition to benzaldehyde
  作者：M.Isabel Burguete、Manuel Collado、Jorge Escorihuela、Francisco Galindo、Eduardo Garcı́a-Verdugo、Santiago V Luis、Marı́a J Vicent

  DOI：10.1016/s0040-4039(03)01705-2

  日期：2003.9

  Ni2+ complexes derived from simple alpha-amino amides catalyze very efficiently the addition of Et2Zn to benzaldehyde, giving (S)-1-phenylethanol as the major isomer in most cases (94% yield, 97% ee for R=Bn). The nature of the substituent on the amide nitrogen atom seems to play a key role in determining the asymmetric induction observed. (C) 2003 Elsevier Ltd. All rights reserved.