3β-hydroperoxy-6α-hydroxy-allohimachal-1-ene | 258268-38-1

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氢过氧化物
• 英文名称: 3β-hydroperoxy-6α-hydroxy-allohimachal-1-ene
• 英文别名: (6R,9R,9aR)-6-hydroperoxy-4,4,6,9a-tetramethyl-1,2,3,7,8,9-hexahydrobenzo[7]annulen-9-ol
• CAS: 258268-38-1
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: OJHMQSCAAKMCMD-BPLDGKMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-hydroperoxy-6α-hydroxy-allohimachal-1-ene 以 氘代氯仿 为溶剂， 生成 (1R,2R,10S)-2,6,6,10-Tetramethyl-9,13-dioxa-tricyclo[8.2.1.0^2,7]tridec-7-ene
  参考文献：
  名称：

  Autoxidation of allohimachalol

  摘要：

  The tri-substituted (2,3)-double bond in allohimachalol (1) undergoes autoxidation in the presence of singlet molecular oxygen, resulting in tertiary and secondary allylic hydroperoxides 6 and 7. These autoxidation products may then participate in complex rearrangement reactions to yield seco-allohimachalanes, which have undergone carbon-carbon bond cleavage at the 2,3- or 3,4-positions. The observed autoxidation/reanangement reactions of 1 in vitro would account for the biogenesis of several allohimachalanes recently reported from the medicinal plant Illicium tsangii as natural products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00938-2
• 作为产物：
  描述：

  allohimachalol 在 氧气 、 亚甲兰 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以47%的产率得到3β-hydroperoxy-6α-hydroxy-allohimachal-1-ene
  参考文献：
  名称：

  Autoxidation of allohimachalol

  摘要：

  The tri-substituted (2,3)-double bond in allohimachalol (1) undergoes autoxidation in the presence of singlet molecular oxygen, resulting in tertiary and secondary allylic hydroperoxides 6 and 7. These autoxidation products may then participate in complex rearrangement reactions to yield seco-allohimachalanes, which have undergone carbon-carbon bond cleavage at the 2,3- or 3,4-positions. The observed autoxidation/reanangement reactions of 1 in vitro would account for the biogenesis of several allohimachalanes recently reported from the medicinal plant Illicium tsangii as natural products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00938-2

文献信息

• Autoxidation of allohimachalol
  作者：Koon-Sin Ngo、Geoffrey D. Brown

  DOI：10.1016/s0040-4020(99)00938-2

  日期：1999.12

  The tri-substituted (2,3)-double bond in allohimachalol (1) undergoes autoxidation in the presence of singlet molecular oxygen, resulting in tertiary and secondary allylic hydroperoxides 6 and 7. These autoxidation products may then participate in complex rearrangement reactions to yield seco-allohimachalanes, which have undergone carbon-carbon bond cleavage at the 2,3- or 3,4-positions. The observed autoxidation/reanangement reactions of 1 in vitro would account for the biogenesis of several allohimachalanes recently reported from the medicinal plant Illicium tsangii as natural products. (C) 1999 Elsevier Science Ltd. All rights reserved.