(4aS,8aR)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-5-methylidenenaphthalen-2(1H)-one | 71883-98-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,8aR)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-5-methylidenenaphthalen-2(1H)-one
• 英文别名: trans-5-Methylen-9-methyl-2-decalon；9-Methyl-5-methylen-trans-dekalon-(2)；1-Methylen-10-methyl-6-decalon；9-Methyl-5-methylen-trans-2-decalon；(4aS,8aR)-8a-methyl-5-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-one
• CAS: 71883-98-2
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: DFBOKKAGBIDLKC-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4aS,8aR)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-5-methylidenenaphthalen-2(1H)-one 在 氢氧化钾 、 sodium acetate 、 乙酸酐 、 二异丁基氢化铝 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 苍术酮
  参考文献：
  名称：

  Dimerization of Butenolide Structures. A Biomimetic Approach to the Dimeric Sesquiterpene Lactones (±)-Biatractylolide and (±)-Biepiasterolide

  摘要：

  The biomimetic synthesis of the bisesquiterpene lactones (+/-)-biatractylolide 1 and (+/-)-biepiasterolide 2 via dimerization of the captodative stabilized radical 8 is reported. Atractylon 7 has also been shown to be a possible intermediate during the biosynthesis of biatractylolide 1, biepiasterolide 2, atractylolide 3, and hydroxyatractylolide 4.

  DOI：

  10.1021/jo0488053
• 作为产物：
  描述：

  芹烷二烯酮 在 aluminum oxide 作用下， 生成 (4aS,8aR)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-5-methylidenenaphthalen-2(1H)-one
  参考文献：
  名称：

  倍半萜类。丽芙。Eudesma-4(14),7(11)-dien-8-one 的绝对构型

  摘要：

  从白术根茎中分离的 (+)-Eudesma-4(14),7(11)-dien-8-one (1) 已被碱性氧化铝降解为 trisnor 酮 (3)。从 1 和 3 的 CD 光谱，已确定 1 的绝对构型为 5S、10R，迄今为止已将其分配给 (-)-对映异构体。

  DOI：

  10.1246/bcsj.52.2439

文献信息

• A general, concise, ‘collective’ approach to eudesmanolide sesquiterpenoids: total synthesis of bioactive atractylenolides I–IV and related natural products
  作者：Subburethinam Ramesh、Goverdhan Mehta

  DOI：10.1016/j.tetlet.2015.08.045

  日期：2015.10

  Total synthesis of seven bioactive atractylenolide-type eudesmanolides from Hagemann’s ester, following, a short, scalable, adaptable, and diversity oriented protocol, has been accomplished. This effort opens a gateway to access through synthesis an exceptionally potent and promising group of natural products and their congeners of contemporary interest.

  按照一个简短，可扩展，适应性强和面向多样性的方案，由哈格曼酯完成了七个生物活性白术内酯型大麦醇内酯的全合成。这项工作为通过合成获得一组异常有效和有前途的天然产物及其具有当代意义的同类产品打开了大门。
• Total synthesis of (±)-atractylon and (±)-lindestrene
  作者：Matthew C. Honan

  DOI：10.1016/s0040-4039(01)84607-4

  日期：——

  The total synthesis of the eudesmane furanosesquiterpenes (±)-atractylon (1) and (±)-lindestrene (2) is described. Both 1 and 2 were synthesized via the methyl xanthate intermediate (10).

  描述了呋喃倍半萜（±）-白术（1）和（±）-林地雌烯（2）的总合成。1和2都是通过黄原酸甲酯中间体（10）合成的。
• Structure-Activity Relationship in Ambergris-Type Woody Odorants possessing a hydronaphthalene skeleton
  作者：Christian Vial、Walter Thommen、Ferdinand Näf

  DOI：10.1002/hlca.19890720628

  日期：1989.9.20

  A series of methyl hydronaphthyl alcohols, formates, acetates, and ketones were prepared and their odour properties evaluated. Minor structural changes, even opposite to the osmophoric group, were found to have major effects on the odour. 13CNMR shift assignments of the hydronaphthyl derivatives are presented.

  制备了一系列甲基氢萘醇，甲酸酯，乙酸酯和酮，并评估了它们的气味特性。发现微小的结构变化，甚至与渗透族相反，对气味有重大影响。给出了萘衍生物的13 CNMR位移分配。
• Banerjee, Ajoy Kumar; Caraballo, Pedro C., Journal of Chemical Research, Miniprint, 1984, # 9, p. 2501 - 2532
  作者：Banerjee, Ajoy Kumar、Caraballo, Pedro C.

  DOI：——

  日期：——
• Biomimetic Synthesis of Biatractylolide and Biepiasterolide
  作者：Sharanjeet K. Bagal、Robert M. Adlington、Jack E. Baldwin、Rodolfo Marquez、Andrew Cowley

  DOI：10.1021/ol035022f

  日期：2003.8.1

  graphicThe biomimetic synthesis of the bisesquiterpenoids biatractylolide 1 and bieplasterolide 2 is reported.