(3aR,7S,8aS,Z)-7-methyl-6-vinyl-3a,4,8,8a-tetrahydro-3H-cyclohepta[b]furan-2(7H)-one | 862387-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aR,7S,8aS,Z)-7-methyl-6-vinyl-3a,4,8,8a-tetrahydro-3H-cyclohepta[b]furan-2(7H)-one
• 英文别名: (3aR,7S,8aS)-7-methyl-6-vinyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one；(3aR,7S,8aS)-6-ethenyl-7-methyl-3,3a,4,7,8,8a-hexahydrocyclohepta[b]furan-2-one
• CAS: 862387-28-8
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: ILWIEGLOFNUUQA-GDPRMGEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aR,7S,8aS,Z)-7-methyl-6-vinyl-3a,4,8,8a-tetrahydro-3H-cyclohepta[b]furan-2(7H)-one 在 六甲基磷酰三胺 、 Hoveyda-Grubbs catalyst second generation 、 二苯基二硒醚 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.33h， 生成 xanthatin
  参考文献：
  名称：

  Asymmetric total syntheses of xanthatin and 11,13-dihydroxanthatin using a stereocontrolled conjugate allylation to γ-butenolide

  摘要：

  The stereocontrolled conjugate allylation to an optically pure gamma-butenolide provided direct and reliable access to a trans-fused series of xanthanolide sesquiterpenoids and allowed for the enantioselective total syntheses of xanthatin and 11,13-dihydroxanthatin to be efficiently achieved. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.077
• 作为产物：
  描述：

  (S,E)-7-(tert-butyldimethylsilyloxy)-6-methylhept-2-en-4-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium diacetate 吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 copper diacetate 、 dimethyl sulfide borane 、 potassium tert-butylate 、 四丁基氟化铵 、 铬酸 、 戴斯-马丁氧化剂 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 29.58h， 生成 (3aR,7S,8aS,Z)-7-methyl-6-vinyl-3a,4,8,8a-tetrahydro-3H-cyclohepta[b]furan-2(7H)-one
  参考文献：
  名称：

  Asymmetric Synthesis of (−)-Dihydroxanthatin by the Stereoselective Oshima−Utimoto Reaction

  摘要：

  The catalytic stereoselective Oshima-Utimoto reaction is useful for the construction of five-membered oxacycles from simple starting materials and was employed for the preparation of the lactone group in the asymmetric synthesis of (-)-11 alpha,13-dihydroxanthatin. Completion of the synthesis is facilitated by ring-closing enyne metathesis and alkene cross metathesis reactions.

  DOI：

  10.1021/ol051276k

文献信息

• Total synthesis of (−)-xanthatin
  作者：Hiromasa Yokoe、Masahiro Yoshida、Kozo Shishido

  DOI：10.1016/j.tetlet.2008.03.081

  日期：2008.5

  The first enantioselective total synthesis of xanthatin, a xanthanolide sesquiterpenoid exhibiting potent antibacterial activity against MRSA, has been accomplished from an optically pure bicyclic lactone, previously synthesized by our group.

  黄嘌呤酮的第一种对映选择性全合成是一种黄嘌呤类倍半萜类化合物，对MRSA表现出强效的抗菌活性，它是由我们小组先前合成的光学纯的双环内酯完成的。
• Asymmetric Synthesis of (−)-Dihydroxanthatin by the Stereoselective Oshima−Utimoto Reaction
  作者：Michael A. Evans、James P. Morken

  DOI：10.1021/ol051276k

  日期：2005.7.1

  The catalytic stereoselective Oshima-Utimoto reaction is useful for the construction of five-membered oxacycles from simple starting materials and was employed for the preparation of the lactone group in the asymmetric synthesis of (-)-11 alpha,13-dihydroxanthatin. Completion of the synthesis is facilitated by ring-closing enyne metathesis and alkene cross metathesis reactions.
• Asymmetric total syntheses of xanthatin and 11,13-dihydroxanthatin using a stereocontrolled conjugate allylation to γ-butenolide
  作者：Kenji Matsumoto、Kuniyoshi Koyachi、Mitsuru Shindo

  DOI：10.1016/j.tet.2012.11.077

  日期：2013.1

  The stereocontrolled conjugate allylation to an optically pure gamma-butenolide provided direct and reliable access to a trans-fused series of xanthanolide sesquiterpenoids and allowed for the enantioselective total syntheses of xanthatin and 11,13-dihydroxanthatin to be efficiently achieved. (C) 2012 Elsevier Ltd. All rights reserved.