(S)-2-(1,8-naphthalimido)-3-hydroxypropanoic acid | 1397997-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (S)-2-(1,8-naphthalimido)-3-hydroxypropanoic acid
• 英文别名: (2S)-2-(1,3-dioxobenzo[de]isoquinolin-2-yl)-3-hydroxypropanoic acid
• CAS: 1397997-05-5
• 化学式: C₁₅H₁₁NO₅
• 分子量: 285.256
• InChiKey: GJTMNYUAOJPCCG-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  94.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(1,8-naphthalimido)-3-hydroxypropanoic acid 在 水 作用下， 以 水 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Cesium complexes of naphthalimide substituted carboxylate ligands: Unusual geometries and extensive cation-π interactions

  摘要：

  The reactions of (1,8-naphthalimido)ethanoic acid (HLgly), and (S)-2-(1,8-naphthalimido)-3-hydroxypropanoic acid (HLser), protonated forms of ligands that contain a carboxylate donor group and a 1,8-naphthalimide pi. . .pi stacking supramolecular tecton, with cesium hydroxide followed by solvothermal treatment in ethanol led to the formation of crystalline Cs(L-gly) (1) and Cs(L-ene) (2), where the L-ene(-) ligand, 2-(1,8-naphthalimido)acrylate, is formed from the dehydration of the User starting material. The X-ray studies show that I crystallizes in the monoclinic space group C2/c with unit cell dimensions a = 30.430(7) angstrom, b = 4.9820(12) angstrom, c = 16.566(4) angstrom, beta = 101.951(4)degrees and 2 in the monoclinic space group P2(1)/n with unit cell dimensions a = 13.6049(15) angstrom, b = 6.8100(8) angstrom, c = 14.4187(16) angstrom, beta = 105.345(2)degrees. The solid state structure of 1 contains two types of 6-coordinate cesium cations linked into sheets by bridging carboxylate oxygen atoms. One cation has a distorted octahedral environment, while the other is in an unusual planar, hexagonal O-6-coordination geometry. The latter geometry is stabilized on both sides of the plane by eta(2)-coordination of naphthalimide rings. The 1,8-naphthalimide rings are involved in intra-sheet pi. . .pi stacking interactions. The O-6 coordination sphere of complex 2 is distorted and only half-filled with the oxygen atoms, which link the cations into rods that are further linked into sheets by bridging interactions of naphthalimide carbonyls with cesium cations from adjacent rods. The open face on the cation has unique eta(2):eta(1) interactions with two methylene groups in the ligands. These sheets are linked into a 3D supramolecular structure by interdigitated 1,8-naphthalimide rings involved in strong pi. . .pi interactions. Both complexes show naphthalimide based fluorescence. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2015.01.046

文献信息

• Homochiral Helical Metal–Organic Frameworks of Group 1 Metals
  作者：Daniel L. Reger、Andrew Leitner、Mark D. Smith、T. Thao Tran、P. Shiv Halasyamani

  DOI：10.1021/ic401327h

  日期：2013.9.3

  state structure based on six-coordinate metals linked into homochiral helical rod secondary building unit (SBU) central cores. In addition to the bonding of the carboxylate and solvent (in the case of Lser the ligand alcohol) to the metals, both oxygens on the 1,8-naphthalimide act as donor groups. One naphthalimide oxygen bonds to the same helical rod SBU as the carboxylate group of that ligand forming

  （S）-2-（1,8-萘二甲酰亚胺）丙酸（H L ala）与（S）-2-（1,8-萘二甲酰亚胺）-3-羟基丙酸（H L ser）的反应呈质子化形式含有羧酸盐供体基团，对映体纯手性中心和1,8-萘二甲酰亚胺π··π堆积超分子构造的配体，在H L ser情况下为醇官能团，其后加适当的碱金属氢氧化物多种结晶方法导致形成晶体K（L ala）（MeOH）（1），K（L ala）（H 2 O）（2），Na（L ala）（H 2 O）（3），K L ser（4），Cs L ser（5）和Cs L ala（6）。这些新复合物均具有基于六配位金属的固态结构，这些金属与同手性螺旋杆二级构建单元（SBU）中央核心相连。除了羧酸盐和溶剂的键合（在L ser的情况下）1，8-萘二甲酰亚胺上的两个氧都充当供体基团。一个萘二甲酰亚胺氧键与该配体的羧酸根基团键合在相同的螺旋杆SBU上，形成螯合物环。另一个萘二甲酰亚胺氧键与相邻的SBU连接。在配合物1
• Homochiral, Helical Coordination Complexes of Lanthanides(III) and Mixed-Metal Lanthanides(III): Impact of the 1,8-Naphthalimide Supramolecular Tecton on Structure, Magnetic Properties, and Luminescence
  作者：Daniel L. Reger、Andrew Leitner、Mark D. Smith

  DOI：10.1021/acs.cgd.5b01387

  日期：2015.11.4

  stacking supramolecular tecton and an alcohol functional group, with La(NO3)3, Ce(NO3)3, SmCl3, Eu(NO3)3, Gd(NO3)3, Tb(NO3)3, and Dy(NO3)3 under solvothermal conditions (water/ethanol) produced single crystals (characterized by single-crystal X-ray crystallography) of [La3(Lser)8(OH)(H2O)]·(H2O,EtOH)x (1), [Ce3(Lser)8(OH)(H2O)]·(H2O,EtOH)x (2), [Sm3(Lser)8(OEt)]·(H2O,EtOH)x (3), [Eu3(Lser)8(OEt)]·(H2O,EtOH)x

  （S）-2-（1,8-萘二甲酰亚胺）-3-羟基丙酸酯（L ser –）的锂盐的反应，这是一种对映体纯的羧酸盐配体，包含1,8-萘二甲酰亚胺π···π堆积的超分子构造和带有La（NO 3）3，Ce（NO 3）3，SmCl 3，Eu（NO 3）3，Gd（NO 3）3，Tb（NO 3）3和Dy（NO 3）的醇官能团3在溶剂热条件下（水/乙醇）制得[La 3（L ser）8（OH）（H 2 O）]·（H 2 O，EtOH）x（1），[Ce 3（L ser）8（OH）（H 2 O）]·（H 2 O，EtOH）x（2），[Sm 3（L ser）8（OEt）]·（H 2 O ，EtOH）x（3），[Eu 3（L ser）8（OEt）]·（H 2 O，EtOH）x（4），[Gd 3（L ser）8（OEt）]·（H 2 O，EtOH）x（5），[Tb 3（L ser）8（OEt）]·（H 2 O，EtOH）x（6），和[Dy