(1S,2R,4R)-1,7,7-trimethyl-2-(2-hydroxy-5-methylphenyl)-bicyclo[2.2.1]heptane | 496866-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R,4R)-1,7,7-trimethyl-2-(2-hydroxy-5-methylphenyl)-bicyclo[2.2.1]heptane
• 英文别名: 4-methyl-2-[(1S,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]phenol；(-)-2-isobornyl-4-methylphenol；2-isobornyl-4-methylphenol；4-methyl-2-((1S,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)phenol；(1S,2R,4R)-2-isobornyl-4-methylphenol；4-Methyl-2-isobornyl-phenol；4-methyl-2-[(1S,2R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]phenol
• CAS: 496866-15-0
• 化学式: C₁₇H₂₄O
• 分子量: 244.377
• InChiKey: ZRCLPBCDJUWMRD-IFIJOSMWSA-N

物化性质

• 沸点：
  296.9±9.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2R,4R)-1,7,7-trimethyl-2-(2-hydroxy-5-methylphenyl)-bicyclo[2.2.1]heptane 以 甲苯 、 苯 为溶剂， 反应 8.5h， 生成 methylpheophorbide a 13(2)'-N-n-octyl-N-(2-hydroxy-3-(1S,2R,4R)-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)-5-methylbenzyl)amide
  参考文献：
  名称：

  Membrane protective properties of diastereomers of methylpheophorbide a 13(2)-N-n-octyl-N-(2-hydroxy-3-isobornyl-5-methylbenzyl)amide

  摘要：

  Two diastereomers of methylpheophorbide a 13(2)-N-n-octyl-N-(2-hydroxy-3-isobornyl-5-methylbenzyl)amide were obtained from (+)- and (-)-enantiomers of 2-isobornyl-4-methylphenol. The evaluation of the membrane protective and antioxidant activity of the individual diastereomers on the model of H2O2-induced hemolysis of blood erythrocytes showed that the stereochemistry of the isobornyl substituent in the synthesized conjugates did not influence their biological activity.

  DOI：

  10.1134/s1068162013040055
• 作为产物：
  描述：

  4-methyl-2-(exo-(1S,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]-hept-2-yl)phenyl (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo-[2.2.1]heptane-1-carboxylate 在 水 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以94%的产率得到(1S,2R,4R)-1,7,7-trimethyl-2-(2-hydroxy-5-methylphenyl)-bicyclo[2.2.1]heptane
  参考文献：
  名称：

  Resolution of racemic 2-isobornyl-4-methylphenol into enantiomers

  摘要：

  通过与（1S）-樟脑酰氯反应将其转化为非对映异构体，成功将外消旋的2-异冰片基-4-甲基苯酚拆分为对映异构体。

  DOI：

  10.1007/s11172-010-0237-6

文献信息

• Synthesis and Configurational Assignment of Chiral Salicylic Aldehydes: Novel Building Blocks for Asymmetric Catalysis
  作者：Albrecht Berkessel、Matthias R. Vennemann、Johann Lex

  DOI：10.1002/1099-0690(200208)2002:16<2800::aid-ejoc2800>3.0.co;2-4

  日期：2002.8

  condensation of the racemic salicylic aldehydes with (R)-phenylglycinol. Finally, the absolute configurations of two of the salicylic aldehydes were established by X-ray crystallography. For this purpose, the (1-phenylethyl)-substituted salicylic aldehyde was condensed with L-valinamide, and the relative configuration of the resulting Schiff base diastereomer 12 was determined. In the second case, the racemic

  我们报告了三个新颖的和手性的水杨醛结构单元6-8的合成，每个都以对映体纯形式存在。这些水杨醛中的两个是从（+）-camp烯制备的，每个都带有一个与水杨酸羟基邻位的[2.2.1]双环庚基取代基。在第三种情况下，在6-位的手性元素是（1-苯乙基）基团。合成序列由的邻位的烷基化对位与任一莰或苯乙烯和随后的甲苯酚邻产物苯酚的-formylation。对映体的色谱分离是通过将外消旋水杨醛与（R）-苯基甘氨醇。最后，通过X射线晶体学确定了两个水杨醛的绝对构型。为此目的，将（1-苯乙基）-取代的水杨醛与L-缬氨酰胺缩合，并且确定所得的席夫碱非对映异构体12的相对构型。在第二种情况下，外消旋中间体苯酚rac - 15在手性固定相上通过HPLC分离，邻位溴化，并通过反常X射线散射进行分析。（©Wiley-VCH Verlag GmbH，69451 Weinheim，Germany，2002）
• Anti-inflammatory activity of isobornylphenol derivatives
  作者：I. Yu. Chukicheva、I. V. Fedorova、E. V. Buravlev、A. E. Lumpov、Yu. B. Vikharev、L. V. Anikina、V. V. Grishko、A. V. Kuchin

  DOI：10.1007/s10600-010-9651-0

  日期：2010.7

  properties [2], is highly promising. The literature teaches that phenols with a bicyclic isobornyl moiety exhibit anti-infection activity [3]. The series of studies performed by us on the synthesis and investigation of terpenophenols showed that some alkylphenols exhibit hemorheological properties and improve brain blood flow [4, 5]. Thus, the synthesis of terpenophenols is critical for further studies of their

  非甾体抗炎药和非麻醉性镇痛药广泛用于治疗各种感染性和非感染性炎症性疾病[1]。以萜酚为基础的新药开发具有独特的药理特性 [2]，前景广阔。文献教导具有双环异冰片基部分的酚类表现出抗感染活性 [3]。我们对萜酚的合成和研究进行的一系列研究表明，一些烷基酚表现出血液流变学特性并改善脑血流量 [4, 5]。因此，萜酚的合成对于进一步研究其生理特性至关重要。在此，我们展示了合成萜酚及其氨甲基衍生物抗炎活性的研究结果。
• Simple synthesis of a terpenophenol—chlorin conjugate with an amide bond
  作者：E. V. Buravlev、I. Yu. Chukicheva、D. V. Belykh、A. V. Kuchin

  DOI：10.1007/s10600-007-0226-7

  日期：2007.11

  A terpenophenol with a butylaminomethyl group was synthesized and conjugated to a chlorin macrocycle through formation of an amide bond without using activating reagents.

  在不使用活化试剂的情况下，通过形成酰胺键，将一种带有丁氨基甲基的萜烯酚与一种氯代大环共轭。
• Synthesis and Some Properties of New Bromo Derivatives of Isobornylphenols
  作者：T. A. Kolegova、I. Yu. Chukicheva、O. G. Shevchenko、A. V. Kutchin

  DOI：10.1134/s1070363223080054

  日期：2023.8

  bromine and N-bromosuccinimide as well as studied oxidative bromination of them with KBr–Oxone®. For obtained brominated derivatives, as isobornylphenols, an assessment of erythrotoxicity, membrane-protective and antioxidant activity was performed using in vitro models. Halogen derivatives of isobornylphenols containing a bromine atom in the para-position and an alkyl fragment in the ortho-position relative

  摘要 我们确定了用分子溴和N-溴代琥珀酰亚胺溴化各种异冰片基酚的最佳条件，并研究了用 KBr–Oxone® 对其进行氧化溴化。对于获得的溴化衍生物，如异冰片基酚，使用体外模型进行了红细胞毒性、膜保护和抗氧化活性的评估。相对于酚羟基在对位含有溴原子且在邻位含有烷基片段的异冰片基酚的卤素衍生物在红细胞氧化溶血模型中表现出高抗氧化活性。
• Buravlev, Evgeny V.; Chukicheva, Irina Y.; Suponitsky, Kyrill Y., Letters in Organic Chemistry, 2011, vol. 8, # 5, p. 301 - 308
  作者：Buravlev, Evgeny V.、Chukicheva, Irina Y.、Suponitsky, Kyrill Y.、Vikharev, Yurii B.、Grishko, Victoria V.、Kutchin, Aleksandr V.

  DOI：——

  日期：——