10,10-Dimethyl-7-methylenebicyclo<6.3.0>undecan-3-one | 163125-81-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 10,10-Dimethyl-7-methylenebicyclo<6.3.0>undecan-3-one
• 英文别名: 2,2-dimethyl-9-methylidene-1,3,3a,4,6,7,8,9a-octahydrocyclopenta[8]annulen-5-one
• CAS: 163125-81-3
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: RMYBJMPBKCYTOH-UHFFFAOYSA-N

物化性质

• 沸点：
  290.9±29.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  10,10-Dimethyl-7-methylenebicyclo<6.3.0>undecan-3-one 在 硫酸 、 silica gel 作用下， 以 正己烷 为溶剂， 以98%的产率得到2,10,10-trimethylbicyclo<6.3.0>undec-2-en-6-one
  参考文献：
  名称：

  Free Radical Fragmentation of [2 + 2] Photoadduct Derivatives. Formal Synthesis of Pentalenene

  摘要：

  A series of [2 + 2] photoadducts 3a-d are converted to cyclobutylcarbinyl iodides 6a-d. Free radical fragmentation of the iodides yields bicyclo[x.y.0] carbon skeletons 7a-d which are present in a variety of natural products. Application of this methodology to terpenoid synthesis is illustrated by the preparation of unsaturated ketone 19 in only six steps (33% overall yield). As 19 has been converted to pentalenene (1) this constitutes a formal synthesis of the angular triquinane sesquiterpenoid.

  DOI：

  10.1021/jo00112a043
• 作为产物：
  描述：

  4,4-二甲基环戊烯 在 咪唑 、 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 对甲苯磺酸 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 16.0h， 生成 10,10-Dimethyl-7-methylenebicyclo<6.3.0>undecan-3-one
  参考文献：
  名称：

  Free Radical Fragmentation of [2 + 2] Photoadduct Derivatives. Formal Synthesis of Pentalenene

  摘要：

  A series of [2 + 2] photoadducts 3a-d are converted to cyclobutylcarbinyl iodides 6a-d. Free radical fragmentation of the iodides yields bicyclo[x.y.0] carbon skeletons 7a-d which are present in a variety of natural products. Application of this methodology to terpenoid synthesis is illustrated by the preparation of unsaturated ketone 19 in only six steps (33% overall yield). As 19 has been converted to pentalenene (1) this constitutes a formal synthesis of the angular triquinane sesquiterpenoid.

  DOI：

  10.1021/jo00112a043

文献信息

• Free Radical Fragmentation of [2 + 2] Photoadduct Derivatives. Formal Synthesis of Pentalenene
  作者：Gordon L. Lange、Christine Gottardo

  DOI：10.1021/jo00112a043

  日期：1995.4

  A series of [2 + 2] photoadducts 3a-d are converted to cyclobutylcarbinyl iodides 6a-d. Free radical fragmentation of the iodides yields bicyclo[x.y.0] carbon skeletons 7a-d which are present in a variety of natural products. Application of this methodology to terpenoid synthesis is illustrated by the preparation of unsaturated ketone 19 in only six steps (33% overall yield). As 19 has been converted to pentalenene (1) this constitutes a formal synthesis of the angular triquinane sesquiterpenoid.