<(1S)-endo>-Bornyl 2-oxophenylacetate | 88195-30-6

• 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: <(1S)-endo>-Bornyl 2-oxophenylacetate
• 英文别名: [(1S,2R,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] 2-oxo-2-phenylacetate
• CAS: 88195-30-6
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: MIWIKSVXLGLTMC-PMUMKWKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  <(1S)-endo>-Bornyl 2-oxophenylacetate 在 rhodium(II) acetate dimer 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 <(1S)-endo>-Bornyl 2-isopropoxyphenylacetate
  参考文献：
  名称：

  Diastereoselectivity in the OH insertion reactions of rhodium carbenoids derived from phenyldiazoacetates of homochiral alcohols

  摘要：

  Rhodium(II) acetate catalysed decomposition of the phenyldiazoacetates 3 in the presence of alcohols (methanol, propan-2-ol, tert-butanol) led to the O-II insertion products 4-6 in varying yields; the diastercomeric excess of the product ranged from 5-53%.

  DOI：

  10.1016/s0040-4039(00)78227-x
• 作为产物：
  描述：

  冰片 、 苯甲酰甲酸 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以91%的产率得到<(1S)-endo>-Bornyl 2-oxophenylacetate
  参考文献：
  名称：

  Diastereoselectivity in the O-H Insertion Reactions of Rhodium Carbenoids Derived from Phenyldiazoacetates of Chiral Alcohols. Preparation of .alpha.-Hydroxy and .alpha.-Alkoxy Esters

  摘要：

  A series of phenyldiazoacetates 3 derived from enantiomerically pure alcohols ((-)-borneol, (+)menthol, (-)-menthol, (-)-8-phenylmenthol, (-)-trans-2-phenylcyclohexanol, (+)-trans-2-phenyl-cyclohexanol, and (-)10-(dicyclohexylsulfamoyl)-D-isoborneol) were prepared from the corresponding alpha-keto esters 1 by way of the tosylhydrazones 2. Rhodium(II)-catalyzed decomposition of the diazoacetates 3 in the presence of water or alcohols resulted in carbenoid O-H insertion reactions to give the corresponding 2-hydroxy- or 2-alkoxyphenylacetates in good yield, but with varying degrees of diastereoselectivity. A range of rhodium(II) and other metal catalysts were investigated, with rhodium(II) acetate and rhodium(II) acetamide giving the best results. The stereochemistry of the major diastereomer was proved in most cases by independent synthesis from a mandelic acid derivative of known configuration. Possible mechanisms are discussed.

  DOI：

  10.1021/jo00119a023

文献信息

• Investigation of chiral induction in photochemical oxetane formation
  作者：H. Koch、J. Runsink、H.-D. Scharft

  DOI：10.1016/s0040-4039(00)88139-3

  日期：1983.1

  The formation of oxetanes from photochemical addition of tetramethylethylene (TME) or diethylketeneacetal with phenylglyoxylic acid esters in the “concave” position leads to high diastereomeric excess (de).

  在“凹”位置通过光化学加成四甲基乙烯（TME）或二乙基酮缩醛与苯乙醛酸酯形成氧杂环丁烷会导致很高的非对映异构体过量（d e）。
• M DMAP-mediated oxidative esterification of α-bromoaryl ketones with alcohols: A facile route to synthesize α-ketoesters
  作者：Ya-jun Zou、Xiang-yu Lu、Li-ji Wu、Xiao-yu Zhang、Ying-wei Wang、Gang Zhao

  DOI：10.1016/j.tetlet.2024.155050

  日期：2024.4

  The use of α-bromoacetophenone and alcohols as starting materials provides easy access to a variety of α-ketoesters, which are important building blocks in organic synthesis. Additionally, metal-free conditions make this methodology more cost-effective compared to traditional metal-catalyzed methods. The wide substrate scope of this methodology means that a variety of different a-ketoesters can be

  使用 α-溴苯乙酮和醇作为起始原料可以轻松获得各种 α-酮酯，它们是有机合成中的重要组成部分。此外，与传统的金属催化方法相比，无金属条件使该方法更具成本效益。该方法的底物范围广泛，意味着可以以优异的产率获得多种不同的α-酮酯，使其成为一种通用且实用的有机合成方法。
• Diastereoselectivity in the O-H Insertion Reactions of Rhodium Carbenoids Derived from Phenyldiazoacetates of Chiral Alcohols. Preparation of .alpha.-Hydroxy and .alpha.-Alkoxy Esters
  作者：Enrique Aller、David S. Brown、Geoffrey G. Cox、David J. Miller、Christopher J. Moody

  DOI：10.1021/jo00119a023

  日期：1995.7

  A series of phenyldiazoacetates 3 derived from enantiomerically pure alcohols ((-)-borneol, (+)menthol, (-)-menthol, (-)-8-phenylmenthol, (-)-trans-2-phenylcyclohexanol, (+)-trans-2-phenyl-cyclohexanol, and (-)10-(dicyclohexylsulfamoyl)-D-isoborneol) were prepared from the corresponding alpha-keto esters 1 by way of the tosylhydrazones 2. Rhodium(II)-catalyzed decomposition of the diazoacetates 3 in the presence of water or alcohols resulted in carbenoid O-H insertion reactions to give the corresponding 2-hydroxy- or 2-alkoxyphenylacetates in good yield, but with varying degrees of diastereoselectivity. A range of rhodium(II) and other metal catalysts were investigated, with rhodium(II) acetate and rhodium(II) acetamide giving the best results. The stereochemistry of the major diastereomer was proved in most cases by independent synthesis from a mandelic acid derivative of known configuration. Possible mechanisms are discussed.
• Diastereoselectivity in the OH insertion reactions of rhodium carbenoids derived from phenyldiazoacetates of homochiral alcohols
  作者：Enrique Aller、Geoffrey G. Cox、David J. Miller、Christopher J. Moody

  DOI：10.1016/s0040-4039(00)78227-x

  日期：1994.8

  Rhodium(II) acetate catalysed decomposition of the phenyldiazoacetates 3 in the presence of alcohols (methanol, propan-2-ol, tert-butanol) led to the O-II insertion products 4-6 in varying yields; the diastercomeric excess of the product ranged from 5-53%.