(R)-2-[(2-nitrophenyl)amino]-2-phenylethanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-[(2-nitrophenyl)amino]-2-phenylethanol
• 英文别名: (2R)-2-(2-nitroanilino)-2-phenylethanol
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: ATKUJXZWUKRLIQ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-[(2-nitrophenyl)amino]-2-phenylethanol 在 氯化亚砜 、 iron(III) chloride hexahydrate 、 potassium carbonate 、 甲烷 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 36.33h， 生成 (1R)-(5H)-1-phenyl-1,2-dihydro-5-methyl-4,6-dioxobenzo[g]imidazo[1,2,3-ij]pteridin-12-ium chloride
  参考文献：
  名称：

  Chiral ethylene-bridged flavinium salts: the stereoselectivity of flavin-10a-hydroperoxide formation and the effect of substitution on the photochemical properties

  摘要：

  A series of chiral non-racemic N-1,N-10-ethylene bridged flavinium salts 4 was prepared using enantiomerically pure 2-substituted 2-aminoethanols (R = isopropyl, phenyl, benzyl, 4-methoxybenzyl, 4-benzyloxybenzyl) derived from amino acids as the sole source of chirality. The flavinium salts were shown to form 10a-hydroperoxy- and 10a-methoxy-adducts with moderate to high diastereoselectivity depending on the ethylene bridge substituent originating from the starting amino acid. High diastereoselectivities (dr values from 80:20 to >95:5) were observed for flavinium salts bearing benzyl substituents attached to the ethylene bridge. The benzyl group preferred the face-to-face (syn) orientation relative to the flavinium unit; thereby effectively preventing nucleophilic attack from one side. This conformation was found to be the most stable according to the DFT calculations. Consequently, the presence of benzyl groups causes intermolecular fluorescence quenching resulting in a significant decrease in the fluorescence quantum yield from 11% for 4a bearing an isopropyl substituent to 0.3% for 4c containing a benzyl group and to a value lower than 0.1% for the benzyloxybenzyl derivative 4e. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.10.029
• 作为产物：
  描述：

  D-苯甘氨醇 、 1-氟-2-硝基苯 在 三乙烯二胺 作用下， 以 正丁醇 为溶剂， 以80%的产率得到(R)-2-[(2-nitrophenyl)amino]-2-phenylethanol
  参考文献：
  名称：

  Chiral ethylene-bridged flavinium salts: the stereoselectivity of flavin-10a-hydroperoxide formation and the effect of substitution on the photochemical properties

  摘要：

  A series of chiral non-racemic N-1,N-10-ethylene bridged flavinium salts 4 was prepared using enantiomerically pure 2-substituted 2-aminoethanols (R = isopropyl, phenyl, benzyl, 4-methoxybenzyl, 4-benzyloxybenzyl) derived from amino acids as the sole source of chirality. The flavinium salts were shown to form 10a-hydroperoxy- and 10a-methoxy-adducts with moderate to high diastereoselectivity depending on the ethylene bridge substituent originating from the starting amino acid. High diastereoselectivities (dr values from 80:20 to >95:5) were observed for flavinium salts bearing benzyl substituents attached to the ethylene bridge. The benzyl group preferred the face-to-face (syn) orientation relative to the flavinium unit; thereby effectively preventing nucleophilic attack from one side. This conformation was found to be the most stable according to the DFT calculations. Consequently, the presence of benzyl groups causes intermolecular fluorescence quenching resulting in a significant decrease in the fluorescence quantum yield from 11% for 4a bearing an isopropyl substituent to 0.3% for 4c containing a benzyl group and to a value lower than 0.1% for the benzyloxybenzyl derivative 4e. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.10.029

文献信息

• A Convergent Approach to Cyclopeptide Alkaloids:  Total Synthesis of Sanjoinine G1
  作者：Taoues Temal-Laïb、Jacqueline Chastanet、Jieping Zhu

  DOI：10.1021/ja0170807

  日期：2002.1.1

  A general strategy for the synthesis of cyclopeptide alkaloids containing an endocyclic aryl-alkyl ether bond has been developed featuring a key intramolecular S(N)Ar reaction. The importance of the N-terminal protective group in the realization of such a strategy is documented. From the appropriate amino acid constituents, the natural sanjoinine G1, a 14-membered para cyclophane, has been synthesized

  已开发出合成包含环内芳基-烷基醚键的环肽生物碱的一般策略，其特征在于关键的分子内 S(N)Ar 反应。N-末端保护基团在实现这种策略中的重要性被记录在案。从适当的氨基酸成分中，天然三连宁 G1，一种 14 元对环芳烷，已分七个步骤合成，总产率为 21%。