(1R,4R,5S,6R)-4-acetoxy-5-bromo-7-oxabicyclo[4.1.0]hept-2-ene | 69945-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1R,4R,5S,6R)-4-acetoxy-5-bromo-7-oxabicyclo[4.1.0]hept-2-ene
• 英文别名: [(1R,2S,3R,6R)-2-bromo-7-oxabicyclo[4.1.0]hept-4-en-3-yl] acetate
• CAS: 69945-46-6
• 化学式: C₈H₉BrO₃
• 分子量: 233.062
• InChiKey: MTYAIYXTDKDYNM-OOJXKGFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4R,5S,6R)-4-acetoxy-5-bromo-7-oxabicyclo[4.1.0]hept-2-ene 、 溶剂黄146 生成 Acetic acid (1R,4S,5R,6R)-4-acetoxy-6-bromo-5-hydroxy-cyclohex-2-enyl ester
  参考文献：
  名称：

  ALTENBACH H.-J.; STEGELMEIER H.; VOGEL E., TETRAHEDRON LETT., 1978, NO 36, 3333-3336

  摘要：

  DOI：
• 作为产物：
  描述：

  (5RS,6RS)-5,6-dibromocyclohex-2-ene-1,4-dione 在 氢氧化钾 、 sodium tetrahydroborate 、 磷脂酶B 作用下， 以 甲苯 为溶剂， 反应 144.0h， 生成 (1R,4R,5S,6R)-4-acetoxy-5-bromo-7-oxabicyclo[4.1.0]hept-2-ene
  参考文献：
  名称：

  Enantioselective Synthesis of (−)-LL-C10037α from Benzoquinone

  摘要：

  The enantioselective total synthesis of the Streptomyces metabolite (-)-LL-C10037 alpha has been accomplished in 10 steps and 20% overall yield. An early chiral intermediate was resolved with Candida rugosa lipase to provide (+)-5 with an enantiomeric excess greater than or equal to 98%. The synthesis is notable in that no protecting groups are required and that all carbons in the core structure of LL-C10037 alpha are derived from the readily available p-benzoquinone.

  DOI：

  10.1021/ol991038n

文献信息

• Highly Functionalized Cyclohexenyl Systems:  Enzymatic Resolution and Selective Oxirane Opening Reactions of <i>p</i>-Benzoquinone Derivatives
  作者：Jeffrey T. Kohrt、Jian-Xin Gu、Carl R. Johnson

  DOI：10.1021/jo980270o

  日期：1998.7.1

  Diol 2, derived in two steps from p-benzoquinone, was converted to epoxy alcohol 3. The latter was resolved with crude Candida rugosa lipase in isopropenyl acetate/toluene to give acetate (-)-4 and residual alcohol (+)-3. Oxirane ring opening reactions of 3 and the corresponding acetate and TBDMS derivatives with a variety of nucleophiles gave diastereomerically pure 3,4,5,6-tetrasubstituted cyclohexene derivatives of type 6. X-ray crystal structures were obtained on compounds 6e, 6m and the diacetate prepared from 6l. Nitrogen nucleophiles provided entry in various aziridines 10. Pd(0)-catalyzed nucleophilic additions to substrate 5 cleanly provided the diastereomeric pattern of type 11. trans-5,6-Disubstituted cyclohexadienes 13 were obtained by an unusual syn-reductive elimination on bromocarbonates 12 utilizing Pd or Zn.