(2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-oxaspiropentane | 287205-34-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-oxaspiropentane
• 英文别名: (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-oxaspiro[2.2]pentane
• CAS: 287205-34-9
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: DRJGIYDYKMSLEP-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-oxaspiropentane 在 lithium perchlorate 作用下， 以 苯 为溶剂， 反应 24.0h， 以85%的产率得到(2S)-2-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-cyclobutanone
  参考文献：
  名称：

  Unexpected Stereochemistry in the Lithium Salt Catalyzed Ring Expansion of Nonracemic Oxaspiropentanes. Formal Syntheses of (−)-(4R,5R)-Muricatacin and the Pheromone (R)-Japonilure

  摘要：

  The stereochemistry of the cyclobutanones 3, obtained by lithium salt catalyzed ring expansion of the optically pure oxaspiropentanes 2, depends not only on the lithium salt but also on the stereochemistry of 2. They constitute the starting material for the syntheses of the acetogenin (-)-(4R,5R)-muricatacin and the pheromone (R)-japonllure.

  DOI：

  10.1021/ol035061r
• 作为产物：
  描述：

  (S)-4-cyclopropylidene-2,2-dimethyl-1,3-dioxolane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到(2R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-oxaspiropentane
  参考文献：
  名称：

  格氏试剂诱导的氧杂螺环戊烷的立体选择性扩环合成叔环丁醇

  摘要：

  研究了格列雅试剂对氧杂螺环戊烷对环丁醇的扩环立体选择性。已经发现该反应通过立体定向形成的环丁酮的中间发生，而格氏试剂对环丁酮羰基的攻击仅在醛衍生的氧杂螺环戊烷的情况下是立体定向的。

  DOI：

  10.1016/s0040-4020(00)00369-0

文献信息

• Synthesis of Tertiary Cyclobutanols through Stereoselective Ring Expansion of Oxaspiropentanes Induced by Grignard Reagents
  作者：Angela M Bernard、Costantino Floris、Angelo Frongia、Pier P Piras

  DOI：10.1016/s0040-4020(00)00369-0

  日期：2000.6

  The stereoselectivity of the ring expansion of oxaspiropentanes to cyclobutanols induced by Grignard reagents has been studied. It has been found that the reaction occurs through the intermediacy of a cyclobutanone, formed stereospecifically, whereas the attack of the Grignard reagent on the carbonyl group of the cyclobutanone is stereospecific only in the case of the oxaspiropentanes derived from

  研究了格列雅试剂对氧杂螺环戊烷对环丁醇的扩环立体选择性。已经发现该反应通过立体定向形成的环丁酮的中间发生，而格氏试剂对环丁酮羰基的攻击仅在醛衍生的氧杂螺环戊烷的情况下是立体定向的。
• Unexpected Stereochemistry in the Lithium Salt Catalyzed Ring Expansion of Nonracemic Oxaspiropentanes. Formal Syntheses of (−)-(4<i>R</i>,5<i>R</i>)-Muricatacin and the Pheromone (<i>R</i>)-Japonilure
  作者：Angela M. Bernard、Angelo Frongia、Pier P. Piras、Francesco Secci

  DOI：10.1021/ol035061r

  日期：2003.8.1

  The stereochemistry of the cyclobutanones 3, obtained by lithium salt catalyzed ring expansion of the optically pure oxaspiropentanes 2, depends not only on the lithium salt but also on the stereochemistry of 2. They constitute the starting material for the syntheses of the acetogenin (-)-(4R,5R)-muricatacin and the pheromone (R)-japonllure.