2-[(2S,3R,4S)-2-hydroxy-6-oxo-4-prop-2-enyloxan-3-yl]ethyl 2,2-dimethylpropanoate | 1147756-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2-[(2S,3R,4S)-2-hydroxy-6-oxo-4-prop-2-enyloxan-3-yl]ethyl 2,2-dimethylpropanoate
• CAS: 1147756-84-0
• 化学式: C₁₅H₂₄O₅
• 分子量: 284.353
• InChiKey: ZQYAKCPYQCSDPS-LOWVWBTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(2S,3R,4S)-2-hydroxy-6-oxo-4-prop-2-enyloxan-3-yl]ethyl 2,2-dimethylpropanoate 在 sodium tetrahydroborate 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Flexible Access to Monoterpenoid Indole Alkaloids Using a Cyclopentanoid Chiral Building Block

  摘要：

  Expedient, diasterocontrolled transformations of 1 to the key synthetic intermediate of corynanthe, iboga, and aspidosperma-class of monoterpenoid indole alkaloids which led up to a formal synthesis of (+)-20R-dihydrocleavamine, (-)-eburnamonine, and a total synthesis of (+)-aspidospermidine (2) have been demonstrated.

  DOI：

  10.3987/com-08-s(f)120
• 作为产物：
  描述：

  在 氢氟酸 作用下， 以 水 、 乙腈 为溶剂， 生成 2-[(2S,3R,4S)-2-hydroxy-6-oxo-4-prop-2-enyloxan-3-yl]ethyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Flexible Access to Monoterpenoid Indole Alkaloids Using a Cyclopentanoid Chiral Building Block

  摘要：

  Expedient, diasterocontrolled transformations of 1 to the key synthetic intermediate of corynanthe, iboga, and aspidosperma-class of monoterpenoid indole alkaloids which led up to a formal synthesis of (+)-20R-dihydrocleavamine, (-)-eburnamonine, and a total synthesis of (+)-aspidospermidine (2) have been demonstrated.

  DOI：

  10.3987/com-08-s(f)120

文献信息

• Flexible Access to Monoterpenoid Indole Alkaloids Using a Cyclopentanoid Chiral Building Block
  作者：Yoshiharu Iwabuchi、Masato Hayashi、Atsushi Satoh、Masatoshi Shibuya、Kunio Ogasawara

  DOI：10.3987/com-08-s(f)120

  日期：——

  Expedient, diasterocontrolled transformations of 1 to the key synthetic intermediate of corynanthe, iboga, and aspidosperma-class of monoterpenoid indole alkaloids which led up to a formal synthesis of (+)-20R-dihydrocleavamine, (-)-eburnamonine, and a total synthesis of (+)-aspidospermidine (2) have been demonstrated.