(-)-8-Phenylmenthyl (R)-2-phenylpropionate | 138291-10-8

• 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: (-)-8-Phenylmenthyl (R)-2-phenylpropionate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (2R)-2-phenylpropanoate
• CAS: 138291-10-8
• 化学式: C₂₅H₃₂O₂
• 分子量: 364.528
• InChiKey: KDZHNLPJGDSPHN-DAVBRLECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-8-Phenylmenthyl (R)-2-phenylpropionate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以76%的产率得到(R)-(+)-2-苯基-1-丙醇
  参考文献：
  名称：

  Stereogenic reactions of the α-carbon radicals of 8-phenylmenthyl esters

  摘要：

  描述了 8-苯基苯甲酯的立体选择性自由基还原和环化过程；主要产物被认为来自于具有与酯的烷氧基对立的较大取代基构象的过渡态。

  DOI：

  10.1039/c39910001603
• 作为产物：
  描述：

  (1'R,2'S,5'R)-2'-(1-methyl-1-phenylethyl)-5'-methylcyclohexyl (R)-2-hydroxy-2-phenylpropanoate 在 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 (-)-8-Phenylmenthyl (R)-2-phenylpropionate
  参考文献：
  名称：

  Stereogenic reactions of the α-carbon radicals of 8-phenylmenthyl esters

  摘要：

  描述了 8-苯基苯甲酯的立体选择性自由基还原和环化过程；主要产物被认为来自于具有与酯的烷氧基对立的较大取代基构象的过渡态。

  DOI：

  10.1039/c39910001603

文献信息

• Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates
  作者：Matthias C Letzel、Hans J Schäfer、Roland Fröhlich

  DOI：10.3762/bjoc.13.5

  日期：——

  Diastereoselective radical coupling was achieved with chiral auxiliaries. The radicals were generated by anodic decarboxylation of five malonic acid derivatives. These were prepared from benzyl malonates and four menthol auxiliaries. Coelectrolyses with 3,3-dimethylbutanoic acid in methanol at platinum electrodes in an undivided cell afforded hetero-coupling products in 22-69% yield with a diastereoselectivity

  非对映选择性自由基偶联是通过手性助剂实现的。这些自由基是通过五种丙二酸衍生物的阳极脱羧反应生成的。它们是由丙二酸苄酯和四种薄荷醇助剂制备的。在未分开的电池中，在铂电极上与甲醇中的3,3-二甲基丁酸进行共电解，可得到杂耦合产物，产率为22-69％，非对映选择性为5至65％de。没有助酸的电解质以21-50％的产率产生非对映异构体均偶联产物，非对映异构体的比率为1.17：2.00：0.81至7.03：2.00。X射线结构分析和13 C NMR数据证实了新的立体异构中心的立体化学。
• Samarium diiodide-mediated asymmetric reactions of 8-phenylmenthyl esters
  作者：Jim-Min Fang、Ming-Yi Chen、Jiann-Shyng Shiue、Ling Lu、Jue-Liang Hsu

  DOI：10.1016/s0040-4039(00)00680-8

  日期：2000.6

  (-)-8-Phenylmenthol was used as a chiral auxiliary to direct asymmetric reactions of its preformed carboxylates. Reduction of xanthates la and Ib by SmI2 likely proceeded via HMPA-bound samarium enolate intermediates. Self- and cross-pinacolic coupling reactions of 8-phenylmenthyl alpha-oxoesters were achieved in a highly stereoselective manner by treatment with SmI2 at -78 degrees C. The stereochemical outcome was consistent with a chelated mode of transition states. (C) 2000 Elsevier Science Ltd. All rights reserved.

  (-)-8-苯基薄荷醇被用作手性辅助剂，用于指导其预先形成的羧酸酯的不对称反应。色烷酸酯la和Ib在SmI2的还原作用下，可能通过HMPA稳定的钐（samarium）烯醇式（enolate）中间体进行反应。在-78°C下，8-苯基薄荷基α-酮酯与SmI2反应，实现了自偶联和交叉偶联反应，且具有高度的立体选择性。其立体化学结果与过渡态的螯合模式一致。©2000 Elsevier Science Ltd. 保留所有权利。
• Diastereoselective Alkylation of 8-Phenylmenthyl Phenylacetate: Aggregated Lithium Enolate versus "Naked" Enolate
  作者：Arlette Solladie-Cavallo、Aurelio G. Csaky、Ingo Gantz、Jean Suffert

  DOI：10.1021/jo00097a041

  日期：1994.9

  It is shown that monoalkylation of 8-phenylmenthyl phenylacetate using lithiated bases leads to poor or no diastereoselectivities (50/50 to 69/31) and high yields (75 to 98%) while alkylation using tBu-P4 (a strong and cation free base, known to provide ''naked'' anion) leads to high diastereoselectivities (92/8 to 98/2) and high yields (65 to 95%). It is postulated that, in the case of phenylacetates, the degree of aggregation of the lithium enolate is responsible of the poor diastereoselectivities.
• Solladie-Cavallo Arlette, Csaky Aurelio G., Gantz Ingo, Suffert Jean, J. Org. Chem, 59 (1994) N 18, S 5343-5346
  作者：Solladie-Cavallo Arlette, Csaky Aurelio G., Gantz Ingo, Suffert Jean

  DOI：——

  日期：——
• Stereogenic reactions of the α-carbon radicals of 8-phenylmenthyl esters
  作者：Ming-Yi Chen、Jim-Min Fang、Yeun-Min Tsai、Ru-Long Yeh

  DOI：10.1039/c39910001603

  日期：——

  The stereoselective free-radical type reduction and cyclisation of 8-phenylmenthyl esters is described; the predominant products are considered to be derived from the transition states with conformations having the larger substituent anti to the alkoxy group of the ester.

  描述了 8-苯基苯甲酯的立体选择性自由基还原和环化过程；主要产物被认为来自于具有与酯的烷氧基对立的较大取代基构象的过渡态。