(3aS)-2,3,3a,4-tetrahydro-1H-5-oxa-9b-aza-cyclopenta[a]naphthalene | 896462-42-3

• 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: (3aS)-2,3,3a,4-tetrahydro-1H-5-oxa-9b-aza-cyclopenta[a]naphthalene
• 英文别名: (3aS)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzoxazine
• CAS: 896462-42-3
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: DNQVLAAXSKWFGI-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aS)-2,3,3a,4-tetrahydro-1H-5-oxa-9b-aza-cyclopenta[a]naphthalene 、 二苯基氯化膦 在 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 为溶剂， 以34%的产率得到[(3aS)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzoxazin-6-yl]-diphenylphosphane
  参考文献：
  名称：

  Chiral P,O-ligands derived from N,O-phenylene prolinols for palladium-catalyzed asymmetric allylic alkylation

  摘要：

  CuI-catalyzed N,O-arylation of (S)-prolinols and 1-bromo-2-iodobenzene afforded cyclic N,O-(1,2-phenylene)prolinols, and subsequent ortho-lithiation and phosphination provided a new type of chiral P,O-ligands. Their palladium-complex-catalyzed asymmetric allylic alkylation of dimethyl malonate with 1,3-diphenyl 2-propenyl acetate gave high yields and good enantioselectivities. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.057
• 作为产物：
  描述：

  L-脯氨酸 在 copper(l) iodide 、 lithium aluminium tetrahydride 、 正丁基锂 、 四甲基乙二胺 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (3aS)-2,3,3a,4-tetrahydro-1H-5-oxa-9b-aza-cyclopenta[a]naphthalene
  参考文献：
  名称：

  Preparation of N-phenyl-(S)-prolinol-derived P,N-ligands and their application in Pd-catalyzed asymmetric allylic alkylation

  摘要：

  Several NPN-type ligands bearing two chiral pyrrolidinyl groups derived from N-phenyl-(S)-prolinol were prepared by two synthetic methods. Their palladium-complex-catalyzed asymmetric allylic alkylation of malonates with 1,3-diphenyl 2-propenyl acetate delivered the products with good to high enantioselectivities (84-97% ee), including an optically active fluorine-containing compound. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.010

文献信息

• Preparation of N-phenyl-(S)-prolinol-derived P,N-ligands and their application in Pd-catalyzed asymmetric allylic alkylation
  作者：Biao Jiang、Zuo-Gang Huang、Ke-Jun Cheng

  DOI：10.1016/j.tetasy.2006.03.010

  日期：2006.3

  Several NPN-type ligands bearing two chiral pyrrolidinyl groups derived from N-phenyl-(S)-prolinol were prepared by two synthetic methods. Their palladium-complex-catalyzed asymmetric allylic alkylation of malonates with 1,3-diphenyl 2-propenyl acetate delivered the products with good to high enantioselectivities (84-97% ee), including an optically active fluorine-containing compound. (c) 2006 Elsevier Ltd. All rights reserved.
• Chiral P,O-ligands derived from N,O-phenylene prolinols for palladium-catalyzed asymmetric allylic alkylation
  作者：Biao Jiang、Zuo-Gang Huang

  DOI：10.1016/j.tetlet.2007.01.057

  日期：2007.3

  CuI-catalyzed N,O-arylation of (S)-prolinols and 1-bromo-2-iodobenzene afforded cyclic N,O-(1,2-phenylene)prolinols, and subsequent ortho-lithiation and phosphination provided a new type of chiral P,O-ligands. Their palladium-complex-catalyzed asymmetric allylic alkylation of dimethyl malonate with 1,3-diphenyl 2-propenyl acetate gave high yields and good enantioselectivities. (c) 2007 Elsevier Ltd. All rights reserved.