[(4S,5S)-4,5-dihydro-4,5-bis[4-(phenylmethoxy)phenyl]isoxazol-3-yl][(3aS,6R,7aR)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1,(4H)-yl]methanone | 1182735-07-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(4S,5S)-4,5-dihydro-4,5-bis[4-(phenylmethoxy)phenyl]isoxazol-3-yl][(3aS,6R,7aR)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1,(4H)-yl]methanone
• CAS: 1182735-07-4
• 化学式: C₄₀H₄₀N₂O₆S
• 分子量: 676.833
• InChiKey: NZBMKTUBOHDWGU-JYEJRJEKSA-N

反应信息

• 作为产物：
  描述：

  1-苯基甲氧基-4-[2-(4-苯基甲氧基苯基)乙烯基]苯 、 在 potassium hydrogencarbonate 作用下， 以 氯仿 为溶剂， 生成 、 [(4S,5S)-4,5-dihydro-4,5-bis[4-(phenylmethoxy)phenyl]isoxazol-3-yl][(3aS,6R,7aR)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1,(4H)-yl]methanone
  参考文献：
  名称：

  由（2 R）-Bornane-10,2-sultam衍生的2-氧乙烷腈的1,3-偶极环加成反应与电子修饰的4,4'-双取代的对苯二酚

  摘要：

  Abstractmagnified imageThanks to its type‐II dipole nature, we were able to demonstrate the higher reactivity of the SO2/CO syn‐conformer for the uncatalyzed 1,3‐dipolar cycloaddition of the 2‐oxoethanenitrile oxide 2 derived from bornane‐10,2‐sultam to the symmetric 4,4′‐disubstituted trans‐stilbenes 3a–3i. The C(α)‐si dipolarophile πy approach along the CO bond precludes the use of the steric rules formerly expressed for this pseudo‐C2‐symmetric auxiliary. The observed diastereoselectivity is related to the electronic nature of the dipolarophile and may be predicted on the basis of its σpara Hammett constant. The absolute configuration was based on the X‐ray structure analysis of cycloadduct (4S,5S)‐4b, which exhibits an SO2/CO anti‐conformation. Finally, the results obtained with cis‐stilbene suggest a nonsynchronous mechanism.

  DOI：

  10.1002/hlca.200800412