(2R)-2-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-cyclobutanone | 594847-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-cyclobutanone
• 英文别名: (2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclobutan-1-one
• CAS: 594847-17-3
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: RAHVDDWGYQHVCC-POYBYMJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-cyclobutanone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到(-)-(4'R,5R)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-4,5-dihydro-2(3H)-furanone
  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：

  (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

文献信息

• 2,2-Dimethyl cyclopentanones by acid catalyzed ring expansion of isopropenylcyclobutanols. A short synthesis of (±)-α-cuparenone and (±)-herbertene
  作者：Angela M. Bernard、Angelo Frongia、Francesco Secci、Pier P. Piras

  DOI：10.1039/b505707h

  日期：——

  catalyzed ring expansion of isopropenylcyclobutanols; the method allows ready access to the family of sesquiterpenes cuparanes and herbertanes, as demonstrated by the synthesis of (+/-)-alpha-cuparenone and the direct precursor of (+/-)-herbertene.

  通过异丙烯基环丁醇的酸催化扩环可以容易地制备2，2-二甲基环戊酮。该方法使得可以容易地获得倍半萜烯铜黄酮和赫伯坦烷类，如（+/-）-α-cuparenone和（+/-）-赫伯汀的直接前体的合成所证明的。
• A highly stereocontrolled formal total synthesis of (±)- and of (−)-grandisol by 1,4-conjugated addition of organocopper reagents to cyclobutylidene derivatives
  作者：Angela M. Bernard、Angelo Frongia、Jean Ollivier、Pier Paolo Piras、Francesco Secci、Marco Spiga

  DOI：10.1016/j.tet.2007.03.134

  日期：2007.6

  Starting from suitable cyclopropanes, a formal total synthesis of racemic grandisol and of the enantiopure (−)-grandisol is presented. The racemic synthesis of the grandisol precursor was accomplished in five steps. The synthesis of the chiral non-racemic precursor (1S,2S,2′R)-cis of this pheromone was realized in 10 steps, with an overall yield of 45%, using the enantiopure cyclobutanone (R,S), previously

  从合适的环丙烷开始，提出了外消旋大扁豆酚和对映纯（-）-大扁豆酚的正式全合成。Grandisol前体的外消旋合成可通过五个步骤完成。手性非外消旋前体的合成（1小号，2小号，2' - [R此信息素） -顺在10个步骤中实现的，具有45％的总产率，使用对映纯的环丁酮（[R ，小号），先前通过光学纯的氧杂螺环戊烷的扩环获得。关键的立体定义步骤是向手性α，β-不饱和环丁烯羰基衍生物中添加二甲基铜锂。