(R)-methyl 2-(2,5,5,8a-tetramethyl-3-oxo-3,5,6,7,8,8a-hexahydronaphthalen-1-yl)acetate | 176238-57-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-methyl 2-(2,5,5,8a-tetramethyl-3-oxo-3,5,6,7,8,8a-hexahydronaphthalen-1-yl)acetate
• 英文别名: methyl 7-oxo-11-homodrima-5,8(9)-dien-12-oate；methyl 7-oxo-11-homodrima-5,8-dien-12-oate；methyl 7-oxo-13,14,15,16-tetranorlabd-5,8(9)-dien-12-oate；methyl 2-[(8aR)-2,5,5,8a-tetramethyl-3-oxo-7,8-dihydro-6H-naphthalen-1-yl]acetate
• CAS: 176238-57-6
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: LSPIOZBHWPANRN-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-(2,5,5,8a-tetramethyl-3-oxo-3,5,6,7,8,8a-hexahydronaphthalen-1-yl)acetate 在 氢氧化钾 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 、 乙醇 、 水 、 乙二醇 为溶剂， 反应 5.75h， 生成 11,12-dibromo-drim-5,8(9)-dien-7-one
  参考文献：
  名称：

  Synthesis of drim-8(9)-en-7-one, drima-5,8(9)-dien-7-one, and their 11,12-dibromo derivatives from norambreinolide

  摘要：

  A method was elaborated for the synthesis of polyfunctional compounds of the drimane series, viz., drim-8(9)-en-7-one, drima-5,8(9)-dien-7-one, and their 11,12-dibromo derivatives, potential intermediates for the synthesis of natural biologically active drimane sesquiterpenoids starting from norambreinolide. The key intermediate of the above drimane compounds is methyl 7-oxo-11-homodrim-8(9)-en-12-oate, prepared by electrochemical oxidation of a mixture of isomeric methyl bicyclohomofamesenoates obtained from norambreinolide.

  DOI：

  10.1007/bf01433763
• 作为产物：
  描述：

  methyl 7-oxo-13,14,15,16-tetranorlabd-8-en-12-oate 在 氧气 、 tetraphenylporphyrin 、 对甲苯磺酸 作用下， 以 四氯化碳 为溶剂， 反应 8.0h， 生成 (R)-methyl 2-(2,5,5,8a-tetramethyl-3-oxo-3,5,6,7,8,8a-hexahydronaphthalen-1-yl)acetate
  参考文献：
  名称：

  Photooxidative dehydrogenation of Δ8-drimen-and Δ8-11-homodrimen-7-ones into α,α ′-dienones

  摘要：

  研究人员详细阐述了将含有 8-en-7-one 结构单元的 drimane 和 11-homodrimane 化合物光氧化脱氢为 α,α′-二烯酮的高效两步法。该方法基于将酮转化为相应的烯醇乙酸酯，然后进行光敏加氧。7-oxo-11-homodrima-5,8-dien-12-oate 甲基、5,6-dehydro-7-ketoisodrimenine、11-acetoxydrima-5,8-dien-7-one 和 11,12-diacetoxydrima-5、分别以 7-oxo-11-homodrim-8-en-12-oate 甲基、7-oxoisodrimenine、11-hydroxydrim-8-en-7-one 和 11,12-diacetoxydrim-8-en-7-one 为起始原料，高产率地制备出了 8-二烯-7-酮。

  DOI：

  10.1007/s11172-006-0316-x

文献信息

• Synthesis of Novel Tetranorlabdane Derivatives with Unprecedented Carbon Skeleton
  作者：Alexandru Ciocarlan、Aculina Aricu、Lidia Lungu、Carolina Edu、Alic Barba、Sergiu Shova、Ionel Mangalagiu、Michele D’Ambrosio、Alina Nicolescu、Calin Deleanu、Nicoleta Vornicu

  DOI：10.1055/s-0036-1588651

  日期：——

  Synthesis of novel tetranorlabdane derivatives including hybride with terpeno-(1,2)-diazine units and dimers with an unprecedented carbon skeleton, was performed based on methyl 7-oxo-13,14,15,16-tetranorlabd-8-en-12-oate intermediate. The structures of the synthesized compounds have been fully confirmed, including by X-ray diffraction, and their antifungal and antibacterial activity was tested. A

  基于甲基 7-oxo-13,14,15,16-tetranorlabd-8-en-12 合成了新型四去甲酸酐衍生物，包括与萜烯-(1,2)-二嗪单元和具有前所未有的碳骨架的二聚体的混合物-燕麦中间体。合成化合物的结构已经得到充分证实，包括通过X射线衍射，并测试了它们的抗真菌和抗菌活性。考虑了环加成反应的可能机制途径。
• Transcription factor modulating compounds and methods of use thereof
  申请人：Levy Stuart B.

  公开号：US20090131401A1

  公开（公告）日：2009-05-21

  Substituted benzoimidazole compounds useful as anti-infectives that decrease resistance, virulence, or growth of microbes are provided. Methods of making and using substituted benzoimidazole compounds, as well as pharmaceutical preparations thereof, in, e.g., reducing antibiotic resistance and inhibiting biofilms.

  本发明提供了可用作抗感染剂的取代苯并咪唑化合物，其可降低微生物的耐药性、毒力或生长。本发明还提供了制备和使用取代苯并咪唑化合物的方法，以及其制备的药物制剂，例如用于减少抗生素耐药性和抑制生物膜的制剂。
• Synthesis of drim-8(9)-en-7-one, drima-5,8(9)-dien-7-one, and their 11,12-dibromo derivatives from norambreinolide
  作者：M. N. Koltsa、G. N. Mironov、S. T. Malinovskii、P. F. Vlad

  DOI：10.1007/bf01433763

  日期：1996.1

  A method was elaborated for the synthesis of polyfunctional compounds of the drimane series, viz., drim-8(9)-en-7-one, drima-5,8(9)-dien-7-one, and their 11,12-dibromo derivatives, potential intermediates for the synthesis of natural biologically active drimane sesquiterpenoids starting from norambreinolide. The key intermediate of the above drimane compounds is methyl 7-oxo-11-homodrim-8(9)-en-12-oate, prepared by electrochemical oxidation of a mixture of isomeric methyl bicyclohomofamesenoates obtained from norambreinolide.
• Photooxidative dehydrogenation of Δ8-drimen-and Δ8-11-homodrimen-7-ones into α,α ′-dienones
  作者：P. F. Vlad、M. N. Coltsa、A. N. Aricu、A. G. Ciocarlan、E. C. Gorincioi、C. G. Edu、C. Deleanu

  DOI：10.1007/s11172-006-0316-x

  日期：2006.4

  An efficient two-step procedure for photooxidative dehydrogenation of drimane and 11-homodrimane compounds containing an 8-en-7-one structural unit into α,α′-dienones was elaborated. The method is based on the transformation of ketones into the respective enol acetates followed by photosensitized oxygenation. Methyl 7-oxo-11-homodrima-5,8-dien-12-oate, 5,6-dehydro-7-ketoisodrimenine, 11-acetoxydrima-5,8-dien-7-one and 11,12-diacetoxydrima-5,8-dien-7-one were prepared in high yields starting from methyl 7-oxo-11-homodrim-8-en-12-oate, 7-oxoisodrimenine, 11-hydroxydrim-8-en-7-one and 11,12-diacetoxydrim-8-en-7-one, respectively.

  研究人员详细阐述了将含有 8-en-7-one 结构单元的 drimane 和 11-homodrimane 化合物光氧化脱氢为 α,α′-二烯酮的高效两步法。该方法基于将酮转化为相应的烯醇乙酸酯，然后进行光敏加氧。7-oxo-11-homodrima-5,8-dien-12-oate 甲基、5,6-dehydro-7-ketoisodrimenine、11-acetoxydrima-5,8-dien-7-one 和 11,12-diacetoxydrima-5、分别以 7-oxo-11-homodrim-8-en-12-oate 甲基、7-oxoisodrimenine、11-hydroxydrim-8-en-7-one 和 11,12-diacetoxydrim-8-en-7-one 为起始原料，高产率地制备出了 8-二烯-7-酮。