(+/-)-(1R*,5R*)-2,2-(Ethylenedioxy)bicyclo<3.1.0>hexane-1-methanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-(1R*,5R*)-2,2-(Ethylenedioxy)bicyclo<3.1.0>hexane-1-methanol
• 英文别名: [(1'R,5'S)-spiro[1,3-dioxolane-2,2'-bicyclo[3.1.0]hexane]-1'-yl]methanol
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: QZYLNCXGYMAFQE-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-(1R*,5R*)-2,2-(Ethylenedioxy)bicyclo<3.1.0>hexane-1-methanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (1'R,5'S)-spiro[1,3-dioxolane-2,2'-bicyclo[3.1.0]hexane]-1'-carbaldehyde
  参考文献：
  名称：

  Ring Contraction of Cyclobutanes and a Novel Cascade Reaction: Application to Synthesis of (.+-.)-Anthoplalone and (.+-.)-Lepidozene

  摘要：

  Two efficient and practical synthetic methodologies for the construction of small ring systems have been developed. The first method involves a novel rearrangement of cyclobutanes 10 and 14 leading to cyclopropanes 11 and 15 employing BF3.OEt(2) or POCl3 in the presence of pyridine or Raney nickel. The second method utilizes a novel cascade reaction of alpha,beta-unsaturated esters 25 and 36 possessing a cyclopropyl ketone moiety with TMSI in the presence of(TMS)(2)NH to afford polycyclic cyclobutane derivatives 26 and 38. A synthesis of(+/-)-anthoplalone (41) and a formal synthesis of (+/-)-lepidozene (42) were achieved utilizing 15, obtained by the above method.

  DOI：

  10.1021/jo00105a028
• 作为产物：
  描述：

  Methyl (+/-)-(1R*,5R*)-2,2-(ethylenedioxy)bicyclo<3.1.0>hexane-1-carboxylate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以96%的产率得到(+/-)-(1R*,5R*)-2,2-(Ethylenedioxy)bicyclo<3.1.0>hexane-1-methanol
  参考文献：
  名称：

  Ring Contraction of Cyclobutanes and a Novel Cascade Reaction: Application to Synthesis of (.+-.)-Anthoplalone and (.+-.)-Lepidozene

  摘要：

  Two efficient and practical synthetic methodologies for the construction of small ring systems have been developed. The first method involves a novel rearrangement of cyclobutanes 10 and 14 leading to cyclopropanes 11 and 15 employing BF3.OEt(2) or POCl3 in the presence of pyridine or Raney nickel. The second method utilizes a novel cascade reaction of alpha,beta-unsaturated esters 25 and 36 possessing a cyclopropyl ketone moiety with TMSI in the presence of(TMS)(2)NH to afford polycyclic cyclobutane derivatives 26 and 38. A synthesis of(+/-)-anthoplalone (41) and a formal synthesis of (+/-)-lepidozene (42) were achieved utilizing 15, obtained by the above method.

  DOI：

  10.1021/jo00105a028