6-(4-戊烯基)-7-氧杂二环[4.1.0]庚烷-2-酮 | 135525-28-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 中文名称: 6-(4-戊烯基)-7-氧杂二环[4.1.0]庚烷-2-酮
• 英文名称: 6-(4-Pentenyl)-7-oxabicyclo<4.1.0>heptan-2-one
• 英文别名: 6-(pent-4-en-1-yl)-7-oxabicyclo[4.1.0]heptan-2-one；6-Pent-4-enyl-7-oxabicyclo[4.1.0]heptan-2-one
• CAS: 135525-28-9
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: RYVUBSZEVYGXBV-UHFFFAOYSA-N

物化性质

• 沸点：
  265.4±23.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(4-戊烯基)-7-氧杂二环[4.1.0]庚烷-2-酮 在 N,N-二甲基丙烯基脲 、 potassium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 25.5h， 生成 6-(Phenyloxy)<6.3.0.0>undecan-5-one
  参考文献：
  名称：

  Intramolecular addition reactions of carbonyl ylides formed during photocyclization of aryl vinyl ethers

  摘要：

  Photocyclization of aryl vinyl ethers reportedly proceeds via carbonyl ylide intermediates. The photochemical behavior of several aryl vinyl ethers, which incorporate a pendant alkene side chain, was explored. Naphthyl vinyl ethers 1c and 1d provided products that are consistent with photocyclization and subsequent intramolecular ylide-alkene addition. Product distribution is influenced by solvent and temperature effects. Thus, irradiation of 1c in toluene provides 9a in 87% yield. However, irradiation of 1c in methanol/toluene (1:1) provides 3c (45%), 11 (24%), and 12 (23%). Product 12 results from photoinitiated intramolecular [2 + 2] cycloaddition of the butenoate ester side chain to the naphthalene system.

  DOI：

  10.1021/jo00019a020
• 作为产物：
  描述：

  3-乙氧基-2-环己烯-1-酮 在 盐酸 、 sodium hydroxide 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 1.75h， 生成 6-(4-戊烯基)-7-氧杂二环[4.1.0]庚烷-2-酮
  参考文献：
  名称：

  Intramolecular addition reactions of carbonyl ylides formed during photocyclization of aryl vinyl ethers

  摘要：

  Photocyclization of aryl vinyl ethers reportedly proceeds via carbonyl ylide intermediates. The photochemical behavior of several aryl vinyl ethers, which incorporate a pendant alkene side chain, was explored. Naphthyl vinyl ethers 1c and 1d provided products that are consistent with photocyclization and subsequent intramolecular ylide-alkene addition. Product distribution is influenced by solvent and temperature effects. Thus, irradiation of 1c in toluene provides 9a in 87% yield. However, irradiation of 1c in methanol/toluene (1:1) provides 3c (45%), 11 (24%), and 12 (23%). Product 12 results from photoinitiated intramolecular [2 + 2] cycloaddition of the butenoate ester side chain to the naphthalene system.

  DOI：

  10.1021/jo00019a020

文献信息

• Enantioselective photocyclisation reactions of 2-aryloxycyclohex-2-enones mediated by a chiral copper-bisoxazoline complex
  作者：Verena Edtmüller、Alexander Pöthig、Thorsten Bach

  DOI：10.1016/j.tet.2017.05.005

  日期：2017.8

  The photocyclisation of the title compounds leads upon direct irradiation at λ = 366 nm in dichloromethane solution to racemic cis-2,3,4a,9b-tetrahydro-1H-dibenzofuran-4-ones (nine examples, 37–74% yield). Since it was found that the substrates show a significant bathochromic absorption shift upon treatment with EtAlCl2, it was attempted to perform the reactions enantioselectively in the presence of

  标题化合物的光环化作用是在二氯甲烷溶液中以λ= 366 nm的直接照射导致外消旋的顺式-2,3,4a，9b-四氢-1 H-二苯并呋喃-4-酮（9个实例，产率37-74％） 。由于发现在用EtAlCl 2处理时底物显示出显着的红移吸收位移，因此试图在手性路易斯酸的存在下对映选择性地进行反应。Cu（ClO 4）2 ·6H 2 O和双恶唑啉配体的络合物具有最佳的对映选择性（最高ee为60％））。据报道对映选择性光环化有两种方法。第一种方案是基于在λ= 368 nm（LED）处直接照射，催化剂负载量为50 mol％，它以26–76％的收率提供了22–40％ee的产物。第二种方案适用于富含电子的2-芳氧基环己-2-烯酮（31-62％收率，29-46％ee），并依赖于噻吨酮（50 mol％）在λ= 419 nm处的敏化作用。
• Radical cyclization of epoxyketones via a 1,5-Bun 3Sn group or a 1,5-H atom transfer
  作者：Sunggak Kim、Jae Suk Koh

  DOI：10.1039/c39920001377

  日期：——

  Radical cyclization of epoxyketones is initiated by Bun3Sn radical addition to epoxyketones, followed by epoxide fragmentation, 1,5-H- or 1,5-Bun3Sn transfer, and cyclization.

  环氧酮的自由基环化由 Bun3Sn 自由基加成环氧酮开始，然后是环氧化物破碎、1,5-H- 或 1,5-Bun3Sn 转移和环化。