6-(3-丁烯基)-7-氧杂二环[4.1.0]庚烷-2-酮 | 117959-90-7

• 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-(3-丁烯基)-7-氧杂二环[4.1.0]庚烷-2-酮
• 英文名称: 6-(3-Butenyl)-7-oxabicyclo<4.1.0>heptan-2-one
• 英文别名: 6-But-3-enyl-7-oxabicyclo[4.1.0]heptan-2-one
• CAS: 117959-90-7
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: CSTWPSSFURTCAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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-(3-丁烯基)-7-氧杂二环[4.1.0]庚烷-2-酮 在 potassium hydride 作用下， 以 甲苯 为溶剂， 反应 28.08h， 生成 10,11-Dihydro-14-methyl-(7aβ,11aβ,14α)-7a,11a-propanobenzonaphtho<1,2-d>thophen-8(9H)-one
  参考文献：
  名称：

  Tandem photocyclization-intramolecular addition reactions of aryl vinyl sulfides. Observation of a novel [2 + 2] cycloaddition-allylic sulfide rearrangement

  摘要：

  Photocyclization of aryl vinyl sulfides reportedly proceeds via thiocarbonyl ylide intermediates. The photochemical behavior of several aryl vinyl sulfides, which incorporate a pendant alkene side chain, was explored. In general, naphthyl and phenyl vinyl thioethers provided products which are consistent with photocyclization to a thiocarbonyl ylide intermediate followed by either intramolecular hydrogen shift or subsequent intramolecular ylide-alkene addition. Product distribution is influenced by solvent and temperature effects. Novel secondary photoprocesses were also observed during some reactions. Thus, irradiation of naphthyl vinyl sulfide 20 gave dihydrothiophene 22 which underwent subsequent intramolecular [2 + 2] cycloaddition to provide 24. Upon prolonged irradiation 24 undergoes a novel allylic sulfide rearrangement to provide 25.

  DOI：

  10.1021/jo00030a022
• 作为产物：
  描述：

  3-(丁-3-烯-1-基)环己-2-烯-1-酮 在 sodium hydroxide 双氧水 作用下， 以 甲醇 为溶剂， 以98%的产率得到6-(3-丁烯基)-7-氧杂二环[4.1.0]庚烷-2-酮
  参考文献：
  名称：

  Stereoselective synthesis of (.+-.)-indolizidines 167B, 205A, and 207A. Enantioselective synthesis of (-)-indolizidine 209B

  摘要：

  DOI：

  10.1021/ja00234a021

文献信息

• SMITH, ADRIAN L.;WILLIAMS, SIMON F.;HOLMES, ANDREW B.;HUGHES, LESLIE R.;L+, J. AMER. CHEM. SOC., 110,(1988) N6, C. 8696-8698
  作者：SMITH, ADRIAN L.、WILLIAMS, SIMON F.、HOLMES, ANDREW B.、HUGHES, LESLIE R.、L+

  DOI：——

  日期：——
• HOLMES, ANDREW B.;SMITH, ADRIAN L.;WILLIAMS, SIMON F.;HUGHES, LESLIE R.;L+, J. ORG. CHEM., 56,(1991) N, C. 1395-1405
  作者：HOLMES, ANDREW B.、SMITH, ADRIAN L.、WILLIAMS, SIMON F.、HUGHES, LESLIE R.、L+

  DOI：——

  日期：——