6-Oxa-7-azatricyclo[6.3.0.01,5]undec-7-ene | 575342-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 6-Oxa-7-azatricyclo[6.3.0.01,5]undec-7-ene
• CAS: 575342-65-3
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: LKFNPAXIEOIBDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Oxa-7-azatricyclo[6.3.0.01,5]undec-7-ene 在 吡啶 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 57.0h， 生成 [(4R,5R,9R)-9-(2,2-dimethylpropanoylamino)spiro[4.4]nonan-4-yl] prop-2-enoate
  参考文献：
  名称：

  Synthesis of a 1,3-spiro-amino-alcohol-derived chiral auxiliary and its application to Diels–Alder reactions

  摘要：

  A short synthesis and resolution of (1R,5R,6R)-6-aminospiro[4.4]nonan-2-ol, 11, is reported. The pivalamide derivative (+)-5 gives excellent diastereo- and regiocontrol as well as endo selectivity as a chiral auxiliary in the BCl3-catalyzed Diels-Alder reaction with a variety of symmetrical and unsymmetrical dienes. The adducts are readily cleaved by saponification, allowing recovery and reuse of (+)-5. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00051-x
• 作为产物：
  描述：

  1-(4-羟基丁基)环戊醇 在 sodium hypochlorite 、 盐酸羟胺 、 草酸 、 sodium carbonate 、 戴斯-马丁氧化剂 作用下， 以 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 33.0h， 生成 6-Oxa-7-azatricyclo[6.3.0.01,5]undec-7-ene
  参考文献：
  名称：

  Synthesis of a 1,3-spiro-amino-alcohol-derived chiral auxiliary and its application to Diels–Alder reactions

  摘要：

  A short synthesis and resolution of (1R,5R,6R)-6-aminospiro[4.4]nonan-2-ol, 11, is reported. The pivalamide derivative (+)-5 gives excellent diastereo- and regiocontrol as well as endo selectivity as a chiral auxiliary in the BCl3-catalyzed Diels-Alder reaction with a variety of symmetrical and unsymmetrical dienes. The adducts are readily cleaved by saponification, allowing recovery and reuse of (+)-5. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00051-x

文献信息

• Synthesis of a 1,3-spiro-amino-alcohol-derived chiral auxiliary and its application to Diels–Alder reactions
  作者：Susan M. Lait、Masood Parvez、Brian A. Keay

  DOI：10.1016/s0957-4166(03)00051-x

  日期：2003.3

  A short synthesis and resolution of (1R,5R,6R)-6-aminospiro[4.4]nonan-2-ol, 11, is reported. The pivalamide derivative (+)-5 gives excellent diastereo- and regiocontrol as well as endo selectivity as a chiral auxiliary in the BCl3-catalyzed Diels-Alder reaction with a variety of symmetrical and unsymmetrical dienes. The adducts are readily cleaved by saponification, allowing recovery and reuse of (+)-5. (C) 2003 Elsevier Science Ltd. All rights reserved.