(1R,2R,4R)-Bicyclo[2.2.2]oct-5-ene-2-carboxylic acid (1R,5R,6R)-6-(2,2-dimethyl-propionylamino)-spiro[4.4]non-1-yl ester | 575343-51-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2R,4R)-Bicyclo[2.2.2]oct-5-ene-2-carboxylic acid (1R,5R,6R)-6-(2,2-dimethyl-propionylamino)-spiro[4.4]non-1-yl ester
• CAS: 575343-51-0
• 化学式: C₂₃H₃₅NO₃
• 分子量: 373.536
• InChiKey: MADFWMDEKYQGKZ-BIKUQWCGSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  528.9±39.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,4R)-Bicyclo[2.2.2]oct-5-ene-2-carboxylic acid (1R,5R,6R)-6-(2,2-dimethyl-propionylamino)-spiro[4.4]non-1-yl ester 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 以93.2%的产率得到bicyclo<2.2.2>octa-5-ene-2-endo-carboxylic acid
  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：

  4-(cyclopent-1-en-1-yl)butan-1-ol 在 吡啶 、 sodium hypochlorite 、 lithium aluminium tetrahydride 、 盐酸羟胺 、 三氯化硼 、 sodium carbonate 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 96.0h， 生成 (1R,2R,4R)-Bicyclo[2.2.2]oct-5-ene-2-carboxylic acid (1R,5R,6R)-6-(2,2-dimethyl-propionylamino)-spiro[4.4]non-1-yl ester
  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