[(4S,5S)-4,5-dihydro-4,5-bis(4-methylphenyl)isoxazol-3-yl][(3aS,6R,7aR)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1,(4H)-yl]methanone | 1182735-00-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: [(4S,5S)-4,5-dihydro-4,5-bis(4-methylphenyl)isoxazol-3-yl][(3aS,6R,7aR)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1,(4H)-yl]methanone
• 英文别名: [(4S,5S)-4,5-bis(4-methylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]methanone；[(4S,5S)-4,5-bis(4-methylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]methanone
• CAS: 1182735-00-7
• 化学式: C₂₈H₃₂N₂O₄S
• 分子量: 492.639
• InChiKey: KDIALHHGCCVEAR-VRQWGWBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,4'-二甲基-反-二苯乙烯 、 在 potassium hydrogencarbonate 作用下， 以 氯仿 为溶剂， 以44%的产率得到[(4S,5S)-4,5-dihydro-4,5-bis(4-methylphenyl)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

文献信息

• 1,3-Dipolar Cycloadditions of a 2-Oxoethanenitrile Oxide Derived from (2<i>R</i>)-Bornane-10,2-sultam to Electronically Modified 4,4′-Disubstituted Stilbenes
  作者：Jan Romanski、Christian Chapuis、Janusz Jurczak

  DOI：10.1002/hlca.200800412

  日期：2009.6

  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.