((3aS,5aS,6S,8S,9bR)-8-Methoxy-2,2-dimethyl-4-methylene-4,5,5a,6,8,9b-hexahydro-3aH-[1,3]dioxolo[4,5-f]isochromen-6-yl)-methanol | 206262-64-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((3aS,5aS,6S,8S,9bR)-8-Methoxy-2,2-dimethyl-4-methylene-4,5,5a,6,8,9b-hexahydro-3aH-[1,3]dioxolo[4,5-f]isochromen-6-yl)-methanol
• 英文别名: [(3aS,5aS,6S,8S,9bR)-8-methoxy-2,2-dimethyl-4-methylidene-3a,5,5a,6,8,9b-hexahydro-[1,3]dioxolo[4,5-f]isochromen-6-yl]methanol
• CAS: 206262-64-8
• 化学式: C₁₅H₂₂O₅
• 分子量: 282.337
• InChiKey: WTAUHSGPLUBZAZ-KLIAIHJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((3aS,5aS,6S,8S,9bR)-8-Methoxy-2,2-dimethyl-4-methylene-4,5,5a,6,8,9b-hexahydro-3aH-[1,3]dioxolo[4,5-f]isochromen-6-yl)-methanol 在 selenium(IV) oxide 、 N-甲基吲哚酮 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 4.0h， 以60%的产率得到(3aS,5R,5aR,6S,8S,9bR)-6-Hydroxymethyl-8-methoxy-2,2-dimethyl-4-methylene-4,5,5a,6,8,9b-hexahydro-3aH-[1,3]dioxolo[4,5-f]isochromen-5-ol
  参考文献：
  名称：

  Stereoelectronic and steric control in chiral cyclohexane synthesis toward (−)-tetrodotoxin

  摘要：

  The synthesis of important intermediates for tetrodotoxin has been explored. The chiral cyclohexane ring was constructed by electrocyclization from a triene precursor and by conversion to the highly oxygenated cyclohexane ring. In particular, the introduction of an a-hydroxy group at the 5 position (toxin-numbering) in tetrodotoxin was achieved by allylic oxidation with SeO(2). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00331-7
• 作为产物：
  描述：

  甲基三苯基碘化膦 、 Acetic acid (3aR,5aS,6S,8S,9bR)-8-methoxy-2,2-dimethyl-4-oxo-4,5,5a,6,8,9b-hexahydro-3aH-[1,3]dioxolo[4,5-f]isochromen-6-ylmethyl ester 在 苯基锂 作用下， 生成 ((3aS,5aS,6S,8S,9bR)-8-Methoxy-2,2-dimethyl-4-methylene-4,5,5a,6,8,9b-hexahydro-3aH-[1,3]dioxolo[4,5-f]isochromen-6-yl)-methanol
  参考文献：
  名称：

  Stereoelectronic and steric control in chiral cyclohexane synthesis toward (−)-tetrodotoxin

  摘要：

  The synthesis of important intermediates for tetrodotoxin has been explored. The chiral cyclohexane ring was constructed by electrocyclization from a triene precursor and by conversion to the highly oxygenated cyclohexane ring. In particular, the introduction of an a-hydroxy group at the 5 position (toxin-numbering) in tetrodotoxin was achieved by allylic oxidation with SeO(2). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00331-7