8-Phenylmenthyl phenylacetate | 156208-22-9

• 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 phenylacetate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-phenylacetate
• CAS: 156208-22-9
• 化学式: C₂₄H₃₀O₂
• 分子量: 350.501
• InChiKey: XCJZCOXJVHBSEH-STZQEDGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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 phenylacetate 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.75h， 生成 (R)-2-phenyl-butan-1-ol
  参考文献：
  名称：

  Diastereoselective Alkylation of 8-Phenylmenthyl Phenylacetate: Aggregated Lithium Enolate versus "Naked" Enolate

  摘要：

  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.

  DOI：

  10.1021/jo00097a041
• 作为产物：
  描述：

  苯乙酸 、 (-)-8-苯基薄荷醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到8-Phenylmenthyl phenylacetate
  参考文献：
  名称：

  丙酮氰醇在α-芳基重氮乙酸铜的铜催化氢氰化反应中作为HCN的来源

  摘要：

  已经开发了使用丙酮氰醇作为氰化氢（HCN）源的Cu催化α-芳基重氮酸酯氢氰化的方法。已经发现，添加三甲基甲硅烷基氰化物（TMSCN）可以通过原位释放游离氰离子来显着加速转化，从而在温和条件下以高收率生产各种类型的α-芳基氰乙酸酯。

  DOI：

  10.1021/jo100356d

文献信息

• Palladium-catalyzed carbenoid based N–H bond insertions: application to the synthesis of chiral α-amino esters
  作者：Gang Liu、Jian Li、Lin Qiu、Li Liu、Guangyang Xu、Bing Ma、Jiangtao Sun

  DOI：10.1039/c3ob41331d

  日期：——

  A highly efficient palladium-catalyzed carbenoid based N–H bond insertion has been developed. The α-amino esters were obtained in high isolated yields. Moreover, by choosing a suitable chiral auxiliary, stereoselective Pd-catalyzed N–H insertion has been realized. The chiral α-amino esters were obtained in high yields (up to 91%) and with excellent diastereoselectivities (d.r. > 19 : 1).

  开发了一种高效的钯催化基于卡宾的N–H键插入反应。得到了高产率的α-氨基酸酯。此外，通过选择合适的立体辅助剂，实现了立体选择性的Pd催化N–H插入反应。得到了高产率（高达91%）和优异的非对映选择性（d.r. > 19:1）的手性α-氨基酸酯。
• Stereochemistry of Silyl Ketene Acetals of Some 8-Phenylmenthyl Arylacetates
  作者：Arlette Solladie-Cavallo、Aurelio G. Csaky

  DOI：10.1021/jo00088a048

  日期：1994.5

  Trimethylsilyl ketene acetals derived from 8-phenylmenthyl phenyl-, p-fluorophenyl, and p-(trifluoromethyl)phenylacetates, methyl phenylacetate, and isopropyl phenylacetate have been studied. It was shown that it is not possible, under kinetic conditions, to form exclusively the desired E-isomer and that the thermodynamic Z-isomer is also obtained as the major product under reaction conditions which can be considered kinetic. The results could be rationalized using the Ireland's and Dauben's models on the basis of the changes in the acidity of the proton to be abstracted and the strength of the base. Dimethyl-tert-butylsilyl ketene acetals have also been studied. It appeared that reaction of TBDMSCl onto the Li-enolates favored the E-isomer. We proposed that, at the temperature (above -20 degrees C) at which the reaction occurs, the E-Z equilibrium between the Li-enolates starts to play a role, and therefore the silyl ketene acetals E/Z ratios are kinetically controlled but by the second step (reaction of the reagent onto the Li-enolate).
• Solladie-Cavallo Arlette, Csaky Aurelio G., J. Org. Chem, 59 (1994) N 9, S 2585-2589
  作者：Solladie-Cavallo Arlette, Csaky Aurelio G.

  DOI：——

  日期：——
• 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：——
• 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.