(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 | 206262-67-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• 英文别名: (3aS,5R,5aR,6S,8S,9bR)-6-(hydroxymethyl)-8-methoxy-2,2-dimethyl-4-methylidene-3a,5,5a,6,8,9b-hexahydro-[1,3]dioxolo[4,5-f]isochromen-5-ol
• CAS: 206262-67-1
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: MMOJUKWXAWJBOD-PMMQCXHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  21
• 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：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (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 在 disodium hydrogenphosphate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成
  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：

  ((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