2-hydroxy-5-methyl-3-((1R,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl)benzaldehyde

• 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: 2-hydroxy-5-methyl-3-((1R,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl)benzaldehyde
• 英文别名: 2-hydroxy-5-methyl-3-{(1R,2S,4S)-1,7,7-trimethylbiyclo[2.2.1]hept-exo-2-yl}benzaldehyde；2-hydroxy-5-methyl-3-[(1R,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]benzaldehyde；2-hydroxy-5-methyl-3-{(1R,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl}benzaldehyde；2-hydroxy-5-methyl-3-[(1R,2S,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]benzaldehyde
• 化学式: C₁₈H₂₄O₂
• 分子量: 272.387
• InChiKey: DRLLUSPWXGBKPT-JCKWVBRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  (1R,2R,3R,5R)-3-(2-aminoethylamino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 、 2-hydroxy-5-methyl-3-((1R,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl)benzaldehyde 以 甲醇 为溶剂， 反应 4.0h， 生成 (1R,2R,3R,5R)-3-[2-(2-hydroxy-5-methyl-3-{(1R,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl}-benzylideneamino)ethylamino]-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol
  参考文献：
  名称：

  Synthesis of chiral 1,2-diamines from α-pinene and their use in asymmetric nitroaldol reaction

  摘要：

  Chiral diamines with C (1) and C (2) symmetry have been synthesized from 2-hydroxypinan-3-one and tested as ligands in Cu-catalyzed asymmetric nitroaldol reaction of nitromethane with 4-nitrobenzaldehyde.

  DOI：

  10.1134/s1070428015040041
• 作为产物：
  描述：

  4-methyl-2-(((R)-1-phenylethylimino)methyl)-6-((1R,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl)phenol 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以98%的产率得到2-hydroxy-5-methyl-3-((1R,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl)benzaldehyde
  参考文献：
  名称：

  具有异冰片基取代基的外消旋水杨醛的简单拆分

  摘要：

  摘要 已通过与 (R)-1-苯乙胺形成非对映异构体对外消旋水杨醛与异冰片基片段 2 进行拆分。

  DOI：

  10.1080/00397910902792648

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）
• Separation of racemic salycylaldehydes containing isobornyl substituent using (R)-1-phenylethylamine
  作者：E. V. Buravlev、I. Yu. Chukicheva、F. M. Dolgushin、A. V. Kuchin

  DOI：10.1134/s1070428010050088

  日期：2010.5

  Racemic salicylaldehydes containing isobornyl substituent were separated by their conversion into diastereomers by the reaction with (R)-1-phenylethylamine. The absolute configuration of the intermediate Schiff bases and separated aldehyde eneatiomers was established by XRD analysis.
• Synthesis of chiral 1,2-diamines from α-pinene and their use in asymmetric nitroaldol reaction
  作者：I. A. Dvornikova、E. V. Buravlev、K. Yu. Suponitskii、I. Yu. Chukicheva、A. V. Kutchin

  DOI：10.1134/s1070428015040041

  日期：2015.4

  Chiral diamines with C (1) and C (2) symmetry have been synthesized from 2-hydroxypinan-3-one and tested as ligands in Cu-catalyzed asymmetric nitroaldol reaction of nitromethane with 4-nitrobenzaldehyde.
• Simple Resolution of Racemic Salicylic Aldehydes Having an Isobornyl Substituent
  作者：Evgeny V. Buravlev、Irina Y. Chukicheva、Aleksandr V. Kutchin

  DOI：10.1080/00397910902792648

  日期：2009.9.18

  Abstract The resolution of the racemic salicylic aldehydes with isobornyl fragment 2 via diastereomer formation with (R)-1-phenylethylamine has been carried out.

  摘要 已通过与 (R)-1-苯乙胺形成非对映异构体对外消旋水杨醛与异冰片基片段 2 进行拆分。