methyl 7-oxo-13,14,15,16-tetranorlabd-8-en-12-oate | 72446-40-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 7-oxo-13,14,15,16-tetranorlabd-8-en-12-oate
• 英文别名: methyl 7-oxo-11-homodrim-8-en-12-oate；(8aS)-Δ¹-carbomethoxymethyl-3-oxo-trans-octahydronaphthalene；methyl 2-[(4aS,8aS)-2,5,5,8a-tetramethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]acetate
• CAS: 72446-40-3
• 化学式: C₁₇H₂₆O₃
• 分子量: 278.392
• InChiKey: YTAQULCZDXWXPY-WMLDXEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  methyl 7-oxo-13,14,15,16-tetranorlabd-8-en-12-oate 在 氢氧化钾 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 四氯化碳 、 乙醇 、 水 、 乙二醇 为溶剂， 反应 6.25h， 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：

  香紫苏醇 在 重氮甲烷 、 氧气 、 铬酸 、 臭氧 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 methyl 7-oxo-13,14,15,16-tetranorlabd-8-en-12-oate
  参考文献：
  名称：

  Vlad, P. F.; Ungur, N. D.; Vorob'eva, E. A., Journal of general chemistry of the USSR, 1986, vol. 56, p. 618 - 629

  摘要：

  DOI：

文献信息

• New Types of Potentially Antimalarial Agents: Epidioxy-substituted norditerpene and norsesterpenes from the marine spongeDiacarnus levii
  作者：Michele D'Ambrosio、Antonio Guerriero、Eric Deharo、C�cile Debitus、Victoria Munoz、Francesco Pietra

  DOI：10.1002/hlca.19980810539

  日期：——

  Natural free carboxylic acids from the hadromerid sponge Diacarnus levii (Kelly-Borges and Vacelet) were esterified to yield the new cyclic norditerpene peroxides ent-muqubilin benzyl ester (= (αR,3S,6R)-α,6-dimethyl-6-[(E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-en-1-yl)hex-3-enyl]-1,2-dioxan-3-acetic acid benzyl ester; 6, diacarnoate B methyl ester(= (αS,3R,6R)-α,6-dimethyl-6-2-(4aS,8aS)-3,4,4a,5

  从hadromerid海绵天然游离羧酸Diacarnus LEVII（凯利-博尔赫斯和Vacelet）进行酯化，以产生新的环状norditerpene过氧化物ENT -muqubilin苄酯（=（α [R，3小号，6 - [R）-α，6-二甲基6-[（（E））-4-甲基-6-（2,6,6-三甲基-环己-1-烯-1-基）己-3-烯基] -1,2-二恶烷-3-乙酸苄基酯; 6，壬烯酸酯B甲酯（=（αS，3 R，6 R）-α，6-二甲基-6- 2-（4a S，8a S）-3,4,4a，5,6， 7,8,8a-八氢-3-氧代-2,5,5,8a-四甲基萘-1-基）乙基} -1,2-二恶烷-3-乙酸甲酯; 9）和脱氧二壬酸酯B苄基酯（=（αS，3 R，6 R）-α，6-二甲基-6- 2-[（（4a S，8a S）-3,4,4a，5,6， 7,8,8a-八氢-2,5,5,8a-四甲基-1-萘基]乙基}
• Synthesis, antibacterial, and antifungal activities of new drimane sesquiterpenoids with azaheterocyclic units
  作者：Aculina Aricu、Alexandru Ciocarlan、Lidia Lungu、Alic Barba、Sergiu Shova、Gheorghita Zbancioc、Ionel I. Mangalagiu、Michele D’Ambrosio、Nicoleta Vornicu

  DOI：10.1007/s00044-016-1665-0

  日期：2016.10

  In order to find new biologically active compounds and in continuation of our work on the synthesis of the novel compounds containing both terpenic and heterocyclic fragments, herein we report the synthesis and assessment of the in vitro antifungal and antibacterial activities of some new drimane sesquiterpenoids with azaheterocyclic fragments. The structures of the synthesized compounds were confirmed

  为了找到新的生物活性化合物，并在我们继续合成包含萜烯和杂环片段的新型化合物的工作中，我们在此报告了一些新的具有氮杂杂环的drimane倍半萜类化合物的体外抗真菌和抗菌活性的合成和评估。碎片。使用核磁共振波谱，质谱，气相色谱和单晶X射线衍射分析确认了合成化合物的结构。进行了微波辅助转换与经典条件的比较研究。已评估了具有氮杂杂环骨架的drimane倍半萜类化合物的体外抗真菌和抗菌活性。分别为-3和3.2×10 -2  µg / ml，在MIC值为1.5 µg / ml时具有另一种良好的抗真菌活性。还报道了与提到的生物活性有关的构效关系。
• 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。
• Vlad, P. F.; Ungur, N. D.; Vorob'eva, E. A., Journal of general chemistry of the USSR, 1986, vol. 56, p. 618 - 629
  作者：Vlad, P. F.、Ungur, N. D.、Vorob'eva, E. A.、Sibirtseva, V. E.

  DOI：——

  日期：——
• 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.