(S)-2-((R)-1-hydroxy-2,2-dimethoxyethyl)cyclobutanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-((R)-1-hydroxy-2,2-dimethoxyethyl)cyclobutanone
• 英文别名: (2S)-2-[(1R)-1-hydroxy-2,2-dimethoxyethyl]cyclobutan-1-one
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: KYSRFCDJONEKQL-IYSWYEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  环丁酮 、 乙二醛-1,1-二甲基乙缩醛溶液 在 N-[(1S)-2'-[[(4-methylphenyl)sulfonyl]amino][1,1'-binaphthalen]-2-yl]-2-pyrrolidinecarboxamide 作用下， 以 水 为溶剂， 反应 48.0h， 以97%的产率得到
  参考文献：
  名称：

  Enantioselective aldol reactions with aqueous 2,2-dimethoxyacetaldehyde organocatalyzed by binam-prolinamides under solvent-free conditions

  摘要：

  Aqueous 2,2-dimethoxyacetaldehyde (60% wt solution) is used as an acceptor in aldol reactions, with cyclic and acyclic ketones and aldehydes as donors, organocatalyzed by 10 mol % of N-tosyl-(S-a)-binam-L-prolinamide [(S-a)-binam-sulfo-L-Pro] at it under solvent-free conditions. The corresponding monoprotected 2-hydroxy-1,4-dicarbonyl compounds are obtained in good yields and with high levels of diastereo- and enantioselectivity mainly as anti-aldols. In the case of 4-substituted cyclohexanones a desymmetrization process takes place to mainly afford the anti,anti-aldols. 2,2-Dimethyl-1,3-dioxan-5-one allows the synthesis of a useful intermediate for the preparation of carbohydrates in higher yield, de and ee than with L-Pro as the organocatalyst. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.08.012

文献信息

• Enantioselective aldol reactions with aqueous 2,2-dimethoxyacetaldehyde organocatalyzed by binam-prolinamides under solvent-free conditions
  作者：Fernando J.N. Moles、Abraham Bañón-Caballero、Gabriela Guillena、Carmen Nájera

  DOI：10.1016/j.tetasy.2014.08.012

  日期：2014.10

  Aqueous 2,2-dimethoxyacetaldehyde (60% wt solution) is used as an acceptor in aldol reactions, with cyclic and acyclic ketones and aldehydes as donors, organocatalyzed by 10 mol % of N-tosyl-(S-a)-binam-L-prolinamide [(S-a)-binam-sulfo-L-Pro] at it under solvent-free conditions. The corresponding monoprotected 2-hydroxy-1,4-dicarbonyl compounds are obtained in good yields and with high levels of diastereo- and enantioselectivity mainly as anti-aldols. In the case of 4-substituted cyclohexanones a desymmetrization process takes place to mainly afford the anti,anti-aldols. 2,2-Dimethyl-1,3-dioxan-5-one allows the synthesis of a useful intermediate for the preparation of carbohydrates in higher yield, de and ee than with L-Pro as the organocatalyst. (C) 2014 Elsevier Ltd. All rights reserved.