10-Hydroxy-(1R)-fenchone | 124509-23-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 10-Hydroxy-(1R)-fenchone
• 英文别名: (1R)-10-hydroxyfenchone；(1S)-10-hydroxyfenchone；10-hydroxyfenchone；(1R,4S)-1-(hydroxymethyl)-3,3-dimethylbicyclo[2.2.1]heptan-2-one
• CAS: 124509-23-5
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: DXBZHTQWANLTPY-OIBJUYFYSA-N

物化性质

• 沸点：
  258.8±13.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-Hydroxy-(1R)-fenchone 在 草酰氯 、 叔丁基锂 、 双(三甲基硅烷基)氨基钾 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 97.25h， 生成
  参考文献：
  名称：

  Paquette, Leo A.; Teleha, Christopher A.; Taylor, Richard T., Journal of the American Chemical Society, 1990, vol. 112, # 1, p. 265 - 277

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R)-1,3,3-三甲基二环[2.2.1]庚-2-酮 在 lithium aluminium tetrahydride 、 hydroxide 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 10-Hydroxy-(1R)-fenchone
  参考文献：
  名称：

  A novel enantiospecific route to 10-hydroxyfenchone: a convenient intermediate for C(10)-O-substituted fenchones

  摘要：

  DOI：

  10.1016/s0957-4166(02)00037-x

文献信息

• Substituent effects on carbon-13 chemical shifts in 1-substituted camphenilones and some derived N-nitro-imines
  作者：Frances C. Brown、David G. Morris

  DOI：10.1039/p29770000125

  日期：——

  In a series of 1-substituted camphenilones (1)–(11) the carbonyl C(2) is markedly shielded by electron-withdrawing substituents. With respect to these camphenilones the corresponding C(2) in a limited series of derived N-nitro-imines (12)–(14) is shielded by ca. 30 p.p.m. The 13C behaviour of fenchone N-nitro-imine is consistent with the existence of configurational isomerism about the C(2)N bond.

  在一系列的1个取代的camp烯（1）–（11）中，羰基C（2）被吸电子取代基显着屏蔽。对于这些樟脑酮，在有限的一系列N-硝基亚胺（12）-（14）中，相应的C（2）被ca屏蔽。30 ppm Fenchone N-硝基亚胺的13 C行为与关于C（2）N键的构型异构现象的存在是一致的。
• Komppa; Klami, Chemische Berichte, 1935, vol. 68, p. 2001
  作者：Komppa、Klami

  DOI：——

  日期：——
• C(10)-Substituted Camphors and Fenchones by Electrophilic Treatment of 2-Methylenenorbornan-1-ols:  Enantiospecificity, Scope, and Limitations
  作者：Santiago de la Moya Cerero、Antonio García Martínez、Enrique Teso Vilar、Amelia García Fraile、Beatriz Lora Maroto

  DOI：10.1021/jo026566i

  日期：2003.2.1

  Valuable chiral sources of C(10)-substituted camphors and C(10)-substituted fenchones can be straightforwardly obtained by treatment of an appropriate, easily obtainable, camphor- or fenchone-derived 2-methylenenorbornan-1-ol with an electrophilic reagent. The process takes place via a tandem regioselective carbon-carbon double-bond addition/stereocontrolled Wagner-Meerwein rearrangement. A complete study of the enantiospecificity, scope, and limitations of this process, as well as about the role played by the hydroxyl group attached at the C(1) bridgehead position of the starting 2-methylenenorbornan-1-ols, has been realized. The feasibility of the described methodology has been exemplified by the highly efficient enantiospecific preparation of several interesting C(10)-halogen-, (C10)-O-, C(10)-S-, C(10)-Se-, or C(10)-C-substituted camphors and fenchones.
• Metabolism of (<b>−</b>)-fenchone by CYP2A6 and CYP2B6 in human liver microsomes
  作者：M. Miyazawa、K. Gyoubu

  DOI：10.1080/00498250600917256

  日期：2007.2

  The in vitro metabolism of (-)-fenchone was examined in human liver microsomes and recombinant enzymes. The biotransformation of (-)-fenchone was investigated by gas chromatography-mass spectrometry. (-)-Fenchone was found to be oxidized to 6-exo-hydroxyfenchone, 6-endo-hydroxyfenchone and 10-hydroxyfenchone by human liver microsomal P450 enzymes. The formation of metabolites was determined by the relative abundance of mass fragments and retention times on gas chromatography (GC). CYP2A6 and CYP2B6 were major enzymes involved in the hydroxylation of (-)-fenchone by human liver microsomes, based on the following lines of evidence. First, of 11 recombinant human P450 enzymes tested, CYP2A6 and CYP2B6 catalysed the oxidation of (-)-fenchone. Second, oxidation of (-)-fenchone was inhibited by thioTEPA and (+)-menthofuran. Finally, there was a good correlation between CYP2A6, CYP2B6 contents and (-)-fenchone hydroxylation activities in liver microsomes of 11 human samples. CYP2A6 may be more important than CYP2B6 in human liver microsomes. Kinetic analysis showed that the V-max/K-m values for (-)fenchone 6-endo-, 6-exo- and 10-hydroxylation catalysed by liver microsomes of human sample HG-03 were 24.3, 44.0 and 1.3nM(-1) min(-1), respectively. Human recombinant CYP2A6 and CYP2B6 catalysed (-)-fenchone 6-exo-hydroxylation with V-max values of 2.7 and 12.9 nmol min(-1) nmol(-1) P450 and apparent K-m values of 0.18 and 0.15 mM and (-)-fenchone 6-endo-hydroxylation with Vmax values of 1.26 and 5.33 nmol min(-1) nmol(-1) P450 with apparent K. values of 0.29 and 0.26 mM. (-)-Fenchone 10-hydroxylation was catalysed by CYP2B6 with K-m and V-max values of 0.2mM and 10.66 nmol min(-1) nmol(-1) P450, respectively.
• A new type of anomalous ozonolysis in strained allylic bicycloalkan-1-ols
  作者：Antonio García Martínez、Enrique Teso Vilar、Amelia García Fraile、Santiago de la Moya Cerero、Beatriz Lora Maroto

  DOI：10.1016/j.tetlet.2005.05.136

  日期：2005.8