[(2S)-2-methylbutyl] 2-benzoyladamantane-2-carboxylate | 314041-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S)-2-methylbutyl] 2-benzoyladamantane-2-carboxylate
• CAS: 314041-56-0
• 化学式: C₂₃H₃₀O₃
• 分子量: 354.489
• InChiKey: JEXCSRPDFPSVHD-VBVZNHOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2S)-2-methylbutyl] 2-benzoyladamantane-2-carboxylate 在 NaY faujasite type zeolite 作用下， 以 正己烷 为溶剂， 生成 4-Benzoyl-adamantane-2-carboxylic acid (S)-2-methyl-butyl ester
  参考文献：
  名称：

  The influence of chiral auxiliaries is enhanced within zeolites

  摘要：

  Zeolites significantly enhance the influence of chiral auxiliaries during photochemical reactions. The generality of this phenomenon has been tested with three independent examples. Chiral auxiliaries that lead to 1:1 mixtures of diastereomers in solution give products in up to 80% diastereomeric excess in the presence of faujasite type zeolites. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01459-3
• 作为产物：
  描述：

  2-methoxymethylene adamantane 在 chromium(VI) oxide 、 草酰氯 、 硫酸 、 水 、 potassium diisopropylamide 、 N,N-二甲基甲酰胺 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 7.5h， 生成 [(2S)-2-methylbutyl] 2-benzoyladamantane-2-carboxylate
  参考文献：
  名称：

  Enhanced Enantio- and Diastereoselectivity via Confinement and Cation Binding:  Yang Photocyclization of 2-Benzoyladamantane Derivatives within Zeolites

  摘要：

  Irradiation of 2-benzoyladamantane derivatives in zeolites yields the endo-cyclobutanols as the only photoproduct via a gamma-hydrogen abstraction process. The cyclobutanols readily undergo retro-aldol reaction to give delta-ketoesters. The enantiomeric excess (ee) in the endo-cyclobutanols is measured by monitoring the ee in the ketoesters. Whereas in solution the ee in the product ketoester is zero, within achiral NaY zeolite, in the presence of a chiral inductor such as pseudoephedrine, ee's up to 28% have been obtained. The influence of zeolite on several chiral esters of 2-benzoyladamantane-2-carboxylic acids has also been examined. Whereas in solution the diastereomeric excess is <15%, in zeolite the delta-ketoesters are obtained in 79% de (best examples). Ab initio computations suggest that enhancement of chiral induction within zeolites is likely to be due to cation complexation with the reactant ketone. Alkali ion-organic interaction, a powerful tool, is waiting to be fully exploited in photochemical and thermal reactions. In this context zeolites could be a useful medium as one could view them as a reservoir of "naked" alkali ions that are only partially coordinated to the zeolite walls.

  DOI：

  10.1021/jo0260793

文献信息

• Enhanced Enantio- and Diastereoselectivity via Confinement and Cation Binding:  Yang Photocyclization of 2-Benzoyladamantane Derivatives within Zeolites
  作者：Arunkumar Natarajan、Abraham Joy、Lakshmi S. Kaanumalle、John R. Scheffer、V. Ramamurthy

  DOI：10.1021/jo0260793

  日期：2002.11.1

  Irradiation of 2-benzoyladamantane derivatives in zeolites yields the endo-cyclobutanols as the only photoproduct via a gamma-hydrogen abstraction process. The cyclobutanols readily undergo retro-aldol reaction to give delta-ketoesters. The enantiomeric excess (ee) in the endo-cyclobutanols is measured by monitoring the ee in the ketoesters. Whereas in solution the ee in the product ketoester is zero, within achiral NaY zeolite, in the presence of a chiral inductor such as pseudoephedrine, ee's up to 28% have been obtained. The influence of zeolite on several chiral esters of 2-benzoyladamantane-2-carboxylic acids has also been examined. Whereas in solution the diastereomeric excess is <15%, in zeolite the delta-ketoesters are obtained in 79% de (best examples). Ab initio computations suggest that enhancement of chiral induction within zeolites is likely to be due to cation complexation with the reactant ketone. Alkali ion-organic interaction, a powerful tool, is waiting to be fully exploited in photochemical and thermal reactions. In this context zeolites could be a useful medium as one could view them as a reservoir of "naked" alkali ions that are only partially coordinated to the zeolite walls.
• The influence of chiral auxiliaries is enhanced within zeolites
  作者：Sivaguru Jayaraman、Sundararajan Uppili、Arunkumar Natarajan、Abraham Joy、Kenneth C.W. Chong、Matthew R. Netherton、Alla Zenova、J.R. Scheffer*、V. Ramamurthy

  DOI：10.1016/s0040-4039(00)01459-3

  日期：2000.10

  Zeolites significantly enhance the influence of chiral auxiliaries during photochemical reactions. The generality of this phenomenon has been tested with three independent examples. Chiral auxiliaries that lead to 1:1 mixtures of diastereomers in solution give products in up to 80% diastereomeric excess in the presence of faujasite type zeolites. (C) 2000 Elsevier Science Ltd. All rights reserved.