(1S)-1-phenyl-3-propyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine | 259151-39-8

• 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: (1S)-1-phenyl-3-propyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine
• 英文别名: (-)-1-phenyl-3-n-propyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine
• CAS: 259151-39-8
• 化学式: C₂₁H₂₁NO
• 分子量: 303.404
• InChiKey: MHGSLRORSIBBDE-QWAKEFERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  21.26
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S)-1-phenyl-3-propyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 (S)-1-{[butyl(methyl)amino](phenyl)methyl}-2-naphthol
  参考文献：
  名称：

  Highly regioselective N-alkylation of nonracemic Betti base: a novel one-pot synthesis of chiral N-methyl-N-alkyl Betti bases

  摘要：

  A novel one-pot preparation of chiral N-methyl-N-alkyl Betti bases has been developed involving a highly regioselective N-alkylation of (S)-(+)-Betti base. The strategy involved formation-cleavage of the oxazine ring and N-methylation with BtCH(2)OH under neutral conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.006
• 作为产物：
  描述：

  正丁醛 、 (S)-(+)-1-(Alpha-氨基苄基)-2-萘酚 以 乙醇 为溶剂， 反应 24.0h， 以68%的产率得到(1S)-1-phenyl-3-propyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine
  参考文献：
  名称：

  与贝蒂碱相关的易得的手性化合物在将二乙基锌对映体选择性加成到芳基醛中的用途

  摘要：

  与Betti碱1相关的手性非外消旋氨基萘家族的现有成员在将二乙基锌催化芳对醛催化对映选择性加成反应中作为络合剂进行了测试。使用这些碱可得到较高的ee值（高达> 99％）。叔氨基萘2可获得最高的ee值。溶剂起着重要作用。还研究了性质和取代基在醛的芳环上的位置的影响。

  DOI：

  10.1016/s0040-4020(99)00914-x

文献信息

• Use of readily available chiral compounds related to the betti base in the enantioselective addition of diethylzinc to aryl aldehydes
  作者：Cosimo Cardellicchio、Giuseppe Ciccarella、Francesco Naso、Filippo Perna、Paolo Tortorella

  DOI：10.1016/s0040-4020(99)00914-x

  日期：1999.12

  complexing agents in the catalytic enantioselective addition of diethylzinc to aryl aldehydes. The use of these bases gave high ee values (up to > 99%). The highest ee values were obtained with the tertiary aminonaphthol 2. An important role was played by the solvent. The effect of the nature and the position of the substituents on the aromatic ring of the aldehyde was also investigated.

  与Betti碱1相关的手性非外消旋氨基萘家族的现有成员在将二乙基锌催化芳对醛催化对映选择性加成反应中作为络合剂进行了测试。使用这些碱可得到较高的ee值（高达> 99％）。叔氨基萘2可获得最高的ee值。溶剂起着重要作用。还研究了性质和取代基在醛的芳环上的位置的影响。
• Highly regioselective N-alkylation of nonracemic Betti base: a novel one-pot synthesis of chiral N-methyl-N-alkyl Betti bases
  作者：Yanmei Dong、Jianwei Sun、Xinyan Wang、Xuenong Xu、Liya Cao、Yuefei Hu

  DOI：10.1016/j.tetasy.2004.04.006

  日期：2004.5

  A novel one-pot preparation of chiral N-methyl-N-alkyl Betti bases has been developed involving a highly regioselective N-alkylation of (S)-(+)-Betti base. The strategy involved formation-cleavage of the oxazine ring and N-methylation with BtCH(2)OH under neutral conditions. (C) 2004 Elsevier Ltd. All rights reserved.