(3S,4R,1'S,3'R,4'R,6'R)-3-[4'-bromo-3',7',7'-trimethylbicyclo(4.1.0)hept-3'-yloxy]-1,4-diphenylazetidin-2-one | 283177-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3S,4R,1'S,3'R,4'R,6'R)-3-[4'-bromo-3',7',7'-trimethylbicyclo(4.1.0)hept-3'-yloxy]-1,4-diphenylazetidin-2-one
• 英文别名: (3R,4S)-3-[[(1S,3R,4R,6R)-4-bromo-3,7,7-trimethyl-3-bicyclo[4.1.0]heptanyl]oxy]-1,4-diphenylazetidin-2-one
• CAS: 283177-14-0
• 化学式: C₂₅H₂₈BrNO₂
• 分子量: 454.407
• InChiKey: VJGWOIJRKVSBQW-NZDKRQHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4R,1'S,3'R,4'R,6'R)-3-[4'-bromo-3',7',7'-trimethylbicyclo(4.1.0)hept-3'-yloxy]-1,4-diphenylazetidin-2-one 在 溶剂黄146 、 锌 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以96%的产率得到cis-3-hydroxy-1,4-diphenylazetidin-2-one
  参考文献：
  名称：

  An efficient synthesis of enantiomerically pure 3-hydroxy-β-lactams via zinc induced removal of a chiral auxiliary

  摘要：

  The diastereoselective synthesis of various beta-lactams 6a-d and 7a-d has been achieved using a chiral acid derived from (+)-+-carene. An efficient zinc induced cleavage of the o-halo ether linkage of these beta-lactams to give enantiomerically pure 3-hydroxy-cis-beta-lactams 8a,b and 9a-d is described. (C) 2000 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0957-4166(00)00098-7
• 作为产物：
  描述：

  (+)-3-蒈烯 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 jones reagent 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 10.0h， 生成 (3S,4R,1'S,3'R,4'R,6'R)-3-[4'-bromo-3',7',7'-trimethylbicyclo(4.1.0)hept-3'-yloxy]-1,4-diphenylazetidin-2-one
  参考文献：
  名称：

  An efficient synthesis of enantiomerically pure 3-hydroxy-β-lactams via zinc induced removal of a chiral auxiliary

  摘要：

  The diastereoselective synthesis of various beta-lactams 6a-d and 7a-d has been achieved using a chiral acid derived from (+)-+-carene. An efficient zinc induced cleavage of the o-halo ether linkage of these beta-lactams to give enantiomerically pure 3-hydroxy-cis-beta-lactams 8a,b and 9a-d is described. (C) 2000 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0957-4166(00)00098-7

文献信息

• An efficient synthesis of enantiomerically pure 3-hydroxy-β-lactams via zinc induced removal of a chiral auxiliary
  作者：Sudhir N Joshi、A.R.A.S Deshmukh、B.M Bhawal

  DOI：10.1016/s0957-4166(00)00098-7

  日期：2000.4

  The diastereoselective synthesis of various beta-lactams 6a-d and 7a-d has been achieved using a chiral acid derived from (+)-+-carene. An efficient zinc induced cleavage of the o-halo ether linkage of these beta-lactams to give enantiomerically pure 3-hydroxy-cis-beta-lactams 8a,b and 9a-d is described. (C) 2000 Elsevier Science Ltd. Ail rights reserved.