(3aR,7S,8aS)-7-methyl-3-methylene-6-vinyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one | 1035901-59-7

• 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)-7-methyl-3-methylene-6-vinyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one
• 英文别名: (3aR,7S,8aS)-6-ethenyl-7-methyl-3-methylidene-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
• CAS: 1035901-59-7
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: LWWRXPBUAMTDTK-AXTRIDKLSA-N

物化性质

• 熔点：
  77.2-77.7 °C(Solv: hexane (110-54-3))
• 沸点：
  355.0±41.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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)-7-methyl-3-methylene-6-vinyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 mogolide C
  参考文献：
  名称：

  仿生合成：黄嘌呤二聚体的发现

  摘要：

  从黄嘌呤开始，仿生合成了一种新型的单体黄原酸酯4β，5β-环氧黄嘌呤-1α，4α-过氧化物。此外，黄嘌呤素的三种不同二聚化以头对头或头尾相接的方式合成了四个前所未有的黄原酸内酯二聚体。值得注意的是，这些二聚体化合物首先在实验室中被鉴定为人工制品，其中两种化合物，Mogolides A和B被证明是Xanthium mogolium Kitag植物中的天然产物。

  DOI：

  10.1002/anie.201406461
• 作为产物：
  描述：

  (4R,5S)-4-allyl-5-[(2S)-3-oxo-2-methylpropyl]dihydrofuran-2(3H)-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 六甲基磷酰三胺 、 二苯基二硒醚 、 potassium tert-butylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 20.08h， 生成 (3aR,7S,8aS)-7-methyl-3-methylene-6-vinyl-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one
  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

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。
• Total synthesis of xanthanolides
  作者：Kazumasa Matsuo、Keiko Ohtsuki、Takashi Yoshikawa、Kozo Shishido、Kaori Yokotani-Tomita、Mitsuru Shindo

  DOI：10.1016/j.tet.2010.08.061

  日期：2010.10

  The total synthesis and determination of the absolute configuration of (+)- and (-)-sundiversifolide have been achieved via intramolecular acylation and Wittig-lactonization as the key steps. The xanthanolide sesquiterpene lactones, 8-epi-xanthatin (1), dihydroxanthatin (2), and xanthatin (3) were also prepared, starting from a common intermediate derived from the synthesis of sundiversifolide. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.
• Biomimetic Synthesis: Discovery of Xanthanolide Dimers
  作者：Hai Shang、Junhua Liu、Ruiyang Bao、Yu Cao、Kun Zhao、Chengqian Xiao、Bing Zhou、Lihong Hu、Yefeng Tang

  DOI：10.1002/anie.201406461

  日期：2014.12.22

  Starting from xanthatin, the biomimetic synthesis of 4β,5β‐epoxyxanthatin‐1α,4α‐endoperoxide, a novel monomeric xanthanolide, has been achieved. Moreover, four unprecedented xanthanolide dimers were synthesized by three different dimerizations of xanthatin, either in a head‐to‐head or head‐to‐tail fashion. Notably, these dimeric compounds were firstly identified as artifacts in the laboratory, and

  从黄嘌呤开始，仿生合成了一种新型的单体黄原酸酯4β，5β-环氧黄嘌呤-1α，4α-过氧化物。此外，黄嘌呤素的三种不同二聚化以头对头或头尾相接的方式合成了四个前所未有的黄原酸内酯二聚体。值得注意的是，这些二聚体化合物首先在实验室中被鉴定为人工制品，其中两种化合物，Mogolides A和B被证明是Xanthium mogolium Kitag植物中的天然产物。