(R)-2-benzoyloxy-4,4-dimethylcyclooctanone

• 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: (R)-2-benzoyloxy-4,4-dimethylcyclooctanone
• 英文别名: (R)-2-(benzoyloxy)cyclooctanone；(R)-2-oxocyclooctyl benzoate；[(1R)-2-oxocyclooctyl] benzoate
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: VUEOPCKULZLDFV-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R,R)-1-benzoyloxy-1,2-epoxycyclooctane 在 ytterbium(III) chloride 作用下， 以 硝基甲烷 为溶剂， 反应 2.0h， 生成 (R)-2-benzoyloxy-4,4-dimethylcyclooctanone
  参考文献：
  名称：

  Dual Mechanisms of Acid-Catalyzed Rearrangement of Enol Ester Epoxides:  Enantioselective Formation of α-Acyloxy Ketones

  摘要：

  DOI：

  10.1021/ja990124f

文献信息

• Enantioselective Synthesis and Stereoselective Rearrangements of Enol Ester Epoxides
  作者：Yuanming Zhu、Lianhe Shu、Yong Tu、Yian Shi

  DOI：10.1021/jo001593z

  日期：2001.3.1

  Enol esters can be epoxidized with high enantioselectivities using the fructose-derived chiral ketone 1 as catalyst and Oxone as oxidant. A detailed study of enantiomerically enriched enol ester epoxides has revealed that the acid-catalyzed rearrangement can proceed through two distinct pathways, one with retention of configuration and the other with inversion. The competition between the two pathways

  可以使用果糖衍生的手性酮1作为催化剂，以Oxone作为氧化剂，以高对映选择性对烯醇酯进行环氧化。对对映异构体富集的烯醇酯环氧化物的详细研究表明，酸催化的重排可以通过两个不同的途径进行，一个保留构型，另一个保留反转。两种途径之间的竞争高度依赖于酸催化剂的性质。强酸有利于保持构型，而弱酸有利于构型转化。在热条件下，这些环氧化物会随着构型的反转而高度立体选择性地重排。的α-酰氧基酮的对映异构体或者可以从烯醇酯环氧化物一种对映体通过反应条件的明智选择来形成。
• Chiral Lewis Acid Catalyzed Resolution of Racemic Enol Ester Epoxides. Conversion of Both Enantiomers of an Enol Ester Epoxide to the Same Enantiomer of Acyloxy Ketone
  作者：Xiaoming Feng、Lianhe Shu、Yian Shi

  DOI：10.1021/jo0108515

  日期：2002.5.1

  enol ester epoxides via a chiral Lewis acid catalyzed rearrangement. Both enantiomerically enriched enol ester epoxides and alpha-acyloxy ketones can be obtained through this resolution. A positive nonlinear effect is observed in this process. By taking advantage of the mechanistic duality in acid-catalyzed enol ester epoxide rearrangement, we can completely convert a racemic enol ester epoxide into an

  本文描述了通过手性路易斯酸催化的重排，有效的外消旋烯醇酯环氧化物的动力学拆分。通过该拆分可以得到对映体富集的烯醇酯环氧化物和α-酰氧基酮。在此过程中观察到正非线性效应。通过利用酸催化的烯醇酯环氧化物重排中的机理对偶性，我们可以通过用催化量的手性路易斯酸处理，然后用催化量的手性路易斯酸处理，将外消旋烯醇酯环氧化物完全转化为对映体富集的α-酰氧基酮。非手性质子酸。
• Enantioselective α-Benzoyloxylation of Ketones Promoted by Primary Amine Catalyst
  作者：Milind S. Jadhav、Paolo Righi、Enrico Marcantoni、Giorgio Bencivenni

  DOI：10.1021/jo2024976

  日期：2012.3.16

  A mixture of 9-amino-(9-deoxy) epi-dihydroquinidine and salicylic acid was able to promote the direct reaction of various cyclohexanones with dibenzoyl peroxide, thus affording the corresponding protected alpha-hydroxy carbonyl compounds in high yield and enantioselectivity. Interestingly the same catalytic salt was found to be active when 1-indanones derivatives were directly employed in the reaction with dibenzoyl peroxide furnishing chiral 1-oxo-2,3-dihydro-1H-inden-2-yl benzoates in high yields and enantioselectivity. Furthermore their treatment with NaBH4 gives easy access to the corresponding enantioenriched 1,2-diols in high yields and without any loss of stereoselectivity.