exo-7-Phenyl-2,6-dioxabicyclo[3.2.0]heptan | 123620-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: exo-7-Phenyl-2,6-dioxabicyclo[3.2.0]heptan
• 英文别名: (1S,5R,7R)-7-phenyl-2,6-dioxabicyclo[3.2.0]heptane
• CAS: 123620-27-9
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: PAAWOMSOXYYIPD-MXWKQRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二氢呋喃 、 苯甲醛 以 苯 为溶剂， 反应 4.0h， 以76%的产率得到
  参考文献：
  名称：

  2,3-二氢呋喃和芳族羰基化合物在Paternò-Büchi反应中的非对映选择性

  摘要：

  苯甲醛和2,3-二氢呋喃之间的Paternò-Büchi反应可以在NaY沸石的空腔内进行。已经观察到增加的立体选择性。当用取代的苯甲醛衍生物进行反应时，观察到不同的立体选择性。假设在HSOMO和LSOMO之间的双自由基中间存在相互作用，可以理解立体选择性。

  DOI：

  10.1016/j.jphotochem.2016.05.001

文献信息

• Temperature and Viscosity Dependence of the Spin-Directed Stereoselectivity of the Carbonyl-Alkene Photocycloaddition
  作者：Axel G. Griesbeck、Samir Bondock、Murthy S. Gudipati

  DOI：10.1002/1521-3773(20011217)40:24<4684::aid-anie4684>3.0.co;2-9

  日期：2001.12.17

  Table. Temperature dependence of the Paterno-Buchi reaktion of 2,3-dihydrofuran (2, 1M und 5M) mit 1a (1M) and 1b (1M and 5M) in n-hexane. temperature [°C] [K] 1/T [K] endo / exo for 2+1a endo / exo for 2+1b (1M) endo / exo for 2+1b (5M) +25 293 0.00341 88 : 12 45.3 : 54.7 47.6 : 52.4 0 273 0.00366 91 : 9 50.5 : 49.5 43.8 : 56.2 -10 263 0.00380 90 : 10 54.6 : 45.4 41.4 : 58.6 -15 258 0.00388 91 : 9

  桌子。2,3-二氢呋喃（2、1M 和 5M）与 1a（1M）和 1b（1M 和 5M）在正己烷中的 Paterno-Buchi 反应的温度依赖性。温度 [°C] [K] 1/T [K] endo / exo 用于 2+1a endo / exo 用于 2+1b (1M) endo / exo 用于 2+1b (5M) +25 293 0.00341 88 : 12 45.3 : 54.7 47.6：52.4 0 27.00366 91：9 50.5：56.2 -10 263 0.00380 10 54.6：45.4：58.6 -15 258 0.0038 91：9 56.6：43.7 -7 -25 248 0.00403 88：12 57.4：42.6 35.7：64.3 -32 241 0.00415 88：121.1 37.1：62.9 -42 231 0.00433 91：9 61.5
• Griesbeck, Axel G.; Stadtmueller, Stefan, Chemische Berichte, 1990, vol. 123, # 2, p. 357 - 362
  作者：Griesbeck, Axel G.、Stadtmueller, Stefan

  DOI：——

  日期：——
• Substantial ²H-Magnetic Isotope Effects on the Diastereoselectivity of Triplet Photocycloaddition Reactions
  作者：Axel G. Griesbeck、Samir Bondock、Peter Cygon

  DOI：10.1021/ja0356232

  日期：2003.7.1

  Magnetic isotope effects (MIE) on the diastereoselectivity of the triplet [2+2]-photocycloaddition of benzaldehyde with 2,3-dihydrofuran are described for four substrate combinations. The MIE results from H/D exchange at the reactive carbons of either the aldehyde or the alkene, respectively, but also from deuteration of the aromatic positions of benzaldehyde. Weaker isotope effects on the diastereoselectivity were detected for the reaction of alpha-deuterated propionaldehyde.
• Stereoselectivity of Triplet Photocycloadditions:¹ Diene−Carbonyl Reactions and Solvent Effects
  作者：Axel G. Griesbeck、Stefan Buhr、Maren Fiege、Hans Schmickler、Johann Lex

  DOI：10.1021/jo971767l

  日期：1998.6.1

  The diastereoselectivity of the photocycloaddition of benzaldehyde to furan was determined (exo/endo = 212:1) and compared with the reaction of other carbonyl compounds and carbonyl analogues. These results were compared with Paterno-Buchi reactions of cycloalkenes and cyclic enol ethers. An increase in steric demand of the a-substituent in benzoyl compounds led to a change in exo/endo-selectivity for furan cycloadditions that was not observed for cycloalkenes or cyclic enol ethers. Different ISC-reactive conformers with enhanced spin-orbit coupling are postulated as a reasonable explanation for the stereoselectivities observed. Additionally, solvent effects were studied, demonstrating the influence of photoinduced electron-transfer steps on the regio- and diastereoselectivity of Paterno-Buchi reactions with 2,3-dihydrofuran in polar solvents. Two bicyclic oxetanes (8 and 10) were characterized by X-ray structure analysis.
• The diastereoselectivity of the Paternò-Büchi reaction between 2,3-dihydrofuran and aromatic carbonyl compounds in organized medium
  作者：Maurizio D’Auria、Francesco Pellegrino、Licia Viggiani

  DOI：10.1016/j.jphotochem.2016.05.001

  日期：2016.7

  The Paternò-Büchi reaction between benzaldehyde and 2,3-dihydrofuran can be performed within the cavity of NaY zeolite. An increased stereoselectivity has been observed. When the reaction was performed with substituted benzaldehyde derivatives, different stereoselectivity has been observed. The stereoselectivity can be understood assuming an interaction in the biradical intermediate between the HSOMO

  苯甲醛和2,3-二氢呋喃之间的Paternò-Büchi反应可以在NaY沸石的空腔内进行。已经观察到增加的立体选择性。当用取代的苯甲醛衍生物进行反应时，观察到不同的立体选择性。假设在HSOMO和LSOMO之间的双自由基中间存在相互作用，可以理解立体选择性。