(R)-3,3-dimethyl-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine | 869116-46-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (R)-3,3-dimethyl-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine
• 英文别名: (1R)-3,3-dimethyl-1-phenyl-1,2-dihydrobenzo[f][1,3]benzoxazine
• CAS: 869116-46-1
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: UICWFECGTWAQEM-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-3,3-dimethyl-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine 在 D-酒石酸 、 sodium carbonate 作用下， 以 水 、 丙酮 为溶剂， 生成 (R)-(-)-1-(Alpha-氨基苄基)-2-萘酚
  参考文献：
  名称：

  柔性自折叠空腔中的对映选择性分子识别

  摘要：

  我们报告了一种基于杯 [5] 芳烃的手性深腔受体，该受体通过氢键协同网络稳定并具有高度灵活的结构。cavitand 显示出对一系列手性季铵盐的对映选择性分子识别，在相应的非对映体主客体复合物之间提供前所未有的稳定性比。分子动力学模拟证实了新宿主的更高灵活性以及与间苯二酚 [4] 芳烃衍生的自折叠腔体有关的优异诱导拟合行为的出现。

  DOI：

  10.1021/acs.orglett.3c00463
• 作为产物：
  描述：

  1-[氨基(苯基)甲基]-2-萘酚 在 硫酸 、 三乙胺 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 生成 (R)-3,3-dimethyl-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine
  参考文献：
  名称：

  An Efficient Kinetic Resolution of Racemic Betti Base Based on an Enantioselective N,O-Deketalization

  摘要：

  [GRAPHIC]An efficient kinetic resolution of racemic Betti base with L-(+)-tartaric acid in acetone was developed based on a novel enantioselective N,O-deketalization, by which the enantiopure R- and S-enantiomers of Betti base were obtained as the corresponding NO-ketal compound and salt with L-(+)-tartaric acid, respectively, in excellent yields with a practically foolproof operation.

  DOI：

  10.1021/jo051328j

文献信息

• Acid promoted CIDT for the deracemization of dihydrocinnamic aldehydes with Betti's base
  作者：Goffredo Rosini、Claudio Paolucci、Francesca Boschi、Emanuela Marotta、Paolo Righi、Francesco Tozzi

  DOI：10.1039/c0gc00013b

  日期：——

  Racemic α-epimerizable and unfunctionalized aldehydes have been converted into enantiomerically enriched mixtures through a sequence of (i) a conversion into the diastereoisomeric 3-substituted 1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines by reaction with the (R)- or (S)-1-(α-aminobenzyl)-2-naphthol (Betti's base), (ii) an acid promoted crystallization-induced diastereoisomer transformation (CIDT), and (iii) a clean cleavage of the dihydro-1,3-naphthoxazinic ring of the enriched diastereoisomer, easily collected by filtration, allowing the recovery of the enantiomerically enriched aldehydes and the chiral auxiliary.

  对映体的α-可互变和未功能化的醛通过以下步骤转化为富含对映体的混合物：(i) 与(R)-或(S)-1-(α-氨基苄基)-2-萘酚（Betti碱）反应，转化为二面体异构体的3-取代1-苯基-2,3-二氢-1H-萘并[1,2-e][1,3]氧杂啉；(ii) 促酸的结晶诱导二面体异构体转化（CIDT）；(iii) 清洁地切割富集的二面体异构体的二氢-1,3-萘氧杂烯环，易于过滤收集，从而回收富含对映体的醛和手性辅助剂。
• Synthesis and characterization of some novel copper(II) complexes with an optically active Betti base
  作者：Shardul Bhatt、Bhavna Trivedi

  DOI：10.1016/j.poly.2011.12.034

  日期：2012.3

  Novel Cu(II) complexes with racemic as well as optically pure 1-(alpha-amino benzyl)-2-napthol, commonly known as Betti base, and its derivative 1-(alpha-pyrrolidinyl benzyl)-2-napthol have been synthesized. The general composition of all the isolated complexes, as determined by elemental analysis, thermal analysis and FAB mass spectra, is found to be Cu(L-H)(2). The coordination of the ligand with metal has been confirmed by IR and ESR spectra of the complexes. The CD spectra of complexes with the S-form of the ligands exhibit a mirror image relationship with the CD spectra of the complexes with the corresponding R-form of the ligands. The Cu(II) complex with racemic Betti base has been characterized structurally. It crystallizes in the monoclinic space group P2(1)/c. The complexes display quasi reversible redox behavior due to the Cu(II)/Cu(I) reduction process. (C) 2012 Elsevier Ltd. All rights reserved.
• An Efficient Kinetic Resolution of Racemic Betti Base Based on an Enantioselective <b><i>N</i></b>,<b><i>O</i></b>-Deketalization
  作者：Yanmei Dong、Rui Li、Jun Lu、Xuenong Xu、Xinyan Wang、Yuefei Hu

  DOI：10.1021/jo051328j

  日期：2005.10.1

  [GRAPHIC]An efficient kinetic resolution of racemic Betti base with L-(+)-tartaric acid in acetone was developed based on a novel enantioselective N,O-deketalization, by which the enantiopure R- and S-enantiomers of Betti base were obtained as the corresponding NO-ketal compound and salt with L-(+)-tartaric acid, respectively, in excellent yields with a practically foolproof operation.