9-oxatricyclo[4.2.1.12,5]dec-7-en-10-one | 84525-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 9-oxatricyclo[4.2.1.12,5]dec-7-en-10-one
• 英文别名: (1R,2R,5S,6S)-9-oxatricyclo[4.2.1.12,5]dec-7-en-10-one
• CAS: 84525-43-9
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: FHOHBNNKNDJQNB-KVFPUHGPSA-N

物化性质

• 沸点：
  80-110 °C(Press: 0.6 Torr)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-oxatricyclo[4.2.1.12,5]dec-7-en-10-one 以81%的产率得到
  参考文献：
  名称：

  FOHLISCH, BALDUR;JOACHIMI, ROLAND, CHEM. BER., 120,(1987) N 12, 1951-1960

  摘要：

  DOI：
• 作为产物：
  描述：

  环戊酮 在 三乙胺 作用下， 以 2,2,2-三氟乙醇 、 乙腈 为溶剂， 生成 9-oxatricyclo[4.2.1.12,5]dec-7-en-10-one
  参考文献：
  名称：

  α-Tosyloxyketones: Convenient [4+3] Cycloaddition Precursors

  摘要：

  开发了一种简明、简便的两步法，用于从酮制备[4+3]环加成产物，采用Koser试剂和三氟乙醇-三乙胺体系。该序列提供的产率与使用α-卤代和α-甲磺酰氧基酮相当，但具有制备简便和中间体稳定性高的优点。

  DOI：

  10.1055/s-2002-20474

文献信息

• Model Studies for the Preparation of Oxepanes and Fused Compounds by Tandem [4+3] Cycloaddition/Ring-Opening Metathesis/Cross Metathesis
  作者：Paolo Disetti、Linda Piras、Maria Moccia、Michele Saviano、Mauro F. A. Adamo

  DOI：10.1002/ejoc.201700994

  日期：2017.11.9

  Functionalised medium-sized ether rings were prepared in an efficient manner by [4+3] cycloaddition followed by ring-opening metathesis. This procedure provided medium-sized rings, which were shown to be useful for the assembly of fused bicyclic structures present in complex natural compounds. The potential of the chemistry described in this paper to be used in synthesis has been demonstrated by the

  通过 [4+3] 环加成和开环复分解以有效的方式制备功能化的中等大小的醚环。该过程提供了中等大小的环，这些环被证明可用于组装复杂天然化合物中存在的稠合双环结构。本文中描述的化学用于合成的潜力已通过功能化的大环醚和双环结构的制备得到证明。
• Lithiumperchlorat/Triethylamin, ein neues Reagens zur Synthese von 3-Oxo-8-oxabicyclo[3.2.1] oct-6-enen aus α-Haloketonen und Furan
  作者：Rolf Herter、Baldur Föhlisch

  DOI：10.1055/s-1982-30033

  日期：——
• Attempted Generation of an Observable Ethano-Bridged (Cyclopentyl) Oxyallyl. The Pericyclic Nature of an Oxyallyl-Oxyallyl Dimerization Reaction
  作者：A. P. Masters、M. Parvez、T. S. Sorensen、F. Sun

  DOI：10.1021/ja00086a013

  日期：1994.4

  An attempt is made to directly observe an ethano-bridged (cyclopentyl) oxyallyl using a synthetic methodolgy which employs aprotic solvents and homogeneous conditions involving a novel organometallic reagent and which can be carried out at very low temperatures. However, even with preparation temperatures of -120 degrees C, the 2,5-dimethylcyclopentyl oxyallyl is not observable by in situ NMR spectroscopy. Products corresponding to an oxyallyl + oxyallyl dimerization are observed instead. The major dimer is a cis-dioxane compound, and the formation of this suggests a process under pericyclic control. An analysis of the allowed molecular orbital overlaps is presented, and it is concluded that the mutual overlap involves all three terminal orbitals (overlap 2 in Figure 2), with preferential bond formation taking place between carbon(A)-oxygen(B), oxygen(A)-carbon(B), where A and B are the two oxyallyl monomers. The dioxane product represents only one of four possible double-connectivity ways in which two oxyallyl units can be joined (see Figure 1). The initially formed cis-dioxane product is quite labile and is easily transformed in a sequential and stereospecific manner into products representative of two of the other three connectivity modes. The formation of the parent cyclopentyl oxyallyl was also studied under the same reaction conditions. In this case one sees no dimeric products, but the formation of the oxyallyl is indicated because [4 + 3] diene adducts of the putative oxyallyl can be trapped, in; accord with previous work in this area.
• Camps, Pelayo; Castane, Joan; Feliz, Miguel, Chemische Berichte, 1989, vol. 122, p. 1313 - 1322
  作者：Camps, Pelayo、Castane, Joan、Feliz, Miguel、Jaime, Carlos、Minguillon, Cristina

  DOI：——

  日期：——
• HERTER, R.;FOEHLISCH, B., SYNTHESIS, BRD, 1982, N 11, 976-979
  作者：HERTER, R.、FOEHLISCH, B.

  DOI：——

  日期：——