bicyclo<12.1.0>pentadec-1(14)-en-7-yn-15-one | 171512-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bicyclo<12.1.0>pentadec-1(14)-en-7-yn-15-one
• 英文别名: bicyclo[12.1.0]pentadeca-1(14)-en-15-one；Bicyclo[12.1.0]pentadec-1(14)-en-7-yn-15-one
• CAS: 171512-59-7
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: QPLRFUUJLAHRQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  bicyclo<12.1.0>pentadec-1(14)-en-7-yn-15-one 生成
  参考文献：
  名称：

  桥联和超桥联的环丙烯亚基亚胺盐

  摘要：

  桥联的环丙烯酮和双桥联的双环丙烯酮与氟硼酸三乙基氧鎓和胺的反应导致桥联和超桥联的环丙烯叉亚基亚胺盐的四氟硼酸酯。

  DOI：

  10.1016/s0040-4039(99)01660-3
• 作为产物：
  描述：

  氯仿 、 1,8-环十四二炔 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以36%的产率得到bicyclo<12.1.0>pentadec-1(14)-en-7-yn-15-one
  参考文献：
  名称：

  Cyclic 2-Ynones from Cyclic Alkynes via Ring Enlargement

  摘要：

  炔烃与三氯甲烷/丁基锂在-78°C 的四氢呋喃中反应，然后水解，可生成 2-炔酮和环丙烯酮。癸-5-炔、环辛炔、环十二-1,6-二炔、环十二-1,7-二炔和环十四-1,8-二炔都是如此。环辛炔首次生成了环-2-炔酮，这证明这种方法甚至适用于合成受约束的环状 2-炔酮。环烷二炔几乎只能单官能团转化为二炔和双环炔酮。

  DOI：

  10.1055/s-1995-4025

文献信息

• CpCo-Mediated Reactions of Cyclopropenones: Access to CpCo-Capped Benzoquinone Complexes
  作者：Andreea Schuster-Haberhauer、Rolf Gleiter、Olivia Körner、Adriane Leskovar、Daniel B. Werz、Felix R. Fischer、Frank Rominger

  DOI：10.1021/om701115w

  日期：2008.4.1

  The reaction of di(n-propyl)cyclopropenone (7), di(n-butyl)cyclopropenone (16), and bicyclo[12.1.0]pentadeca-1(14)-en-7-yn-15-one (21) with CpCo(CO)(2) and CpCo(cod) yielded CpCo-complexed benzoquinone and cyclopentadienone derivatives. When 16 was reacted with CPCO(CO)(2) and a 10-fold surplus of 4-octyne, a mixture of CpCo-capped benzoquinone 25 and cyclopentadienone 26 was isolated. The reaction of cyclopropenone 16 containing a C-13-labeled CO group with CPCO(CO)(2) yielded a CpCo-capped tetrakis(n-butyl)-p-benzoquinone with one C-13 nucleus per molecule as the main product. The mechanism of the formation of p-benzoquinone is discussed on the basis of the results of trapping and labeling experiments.
• Doubly Bridged Biscyclopropenones, a New Family of Phanes
  作者：Rolf Gleiter、Martin Merger、Annegret Altreuther、Hermann Irngartinger

  DOI：10.1021/jo9515539

  日期：1996.1.1

  The first representatives, 10-12, of the new species of double-decked cyclopropenonophanes were synthesized by cycloaddition reactions of dichlorocarbene to alkynylenecyclopropenonophanes 7-9 followed by hydrolysis as well as in an alternative route involving hydride abstraction from dichlorotricycloalkadienes 16 and 17 to dichlorocyclopropenyliophanes and in situ hydrolysis of the latter. The X-ray analysis of [3.3]cyclopropenonophane 10 reveals a considerable tetragonalization of the bridgehead carbon atoms, indicating a significant deformation of the cyclopropenone moieties in the phane corset, According to ab initio calculations, the it orbitals of the cyclopropenones display transannular interactions of nearly the same scale as found in 7.