(R)-5-chloro-1-oxo-2,3-dihydro-1H-inden-2-yl benzoate | 1363514-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (R)-5-chloro-1-oxo-2,3-dihydro-1H-inden-2-yl benzoate
• 英文别名: [(2R)-6-chloro-3-oxo-1,2-dihydroinden-2-yl] benzoate
• CAS: 1363514-51-5
• 化学式: C₁₆H₁₁ClO₃
• 分子量: 286.715
• InChiKey: XTRCJTRBYGVXLP-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  5-氯-1-茚酮 、 过氧化苯甲酰 在 (9R)-10,11-二氢-6'-甲氧基奎宁-9-胺三盐酸盐 、 sodium carbonate 、 水杨酸 作用下， 以 甲苯 为溶剂， 反应 80.0h， 生成 (S)-5-chloro-1-oxo-2,3-dihydro-1H-inden-2-yl benzoate 、 (R)-5-chloro-1-oxo-2,3-dihydro-1H-inden-2-yl benzoate
  参考文献：
  名称：

  Enantioselective α-Benzoyloxylation of Ketones Promoted by Primary Amine Catalyst

  摘要：

  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.

  DOI：

  10.1021/jo2024976

文献信息

• 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.