(S)-ethyl 2-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-4-oxopentanoate | 1088105-31-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (S)-ethyl 2-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-4-oxopentanoate
• 英文别名: ethyl (2S)-2-[(2R)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-4-oxopentanoate
• CAS: 1088105-31-0
• 化学式: C₂₆H₃₆O₄Si
• 分子量: 440.655
• InChiKey: NOPKIZSTJZPNDY-RDPSFJRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-ethyl 2-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-4-oxopentanoate
  参考文献：
  名称：

  Organocatalytic Michael Addition of Aldehydes to γ-Keto-α,β-unsaturated Esters. An Efficient Entry to Versatile Chiral Building Blocks

  摘要：

  The diarylprolinol ether/HOAc-catalyzed Michael addition of aldehydes to gamma-keto-alpha,beta-unsaturated esters occurs in a highly regioselective and enantioselective manner. The adducts could easily be converted into synthetically useful cyclohexenones, cyclohexanones, piperidines, and gamma-lactones.

  DOI：

  10.1021/ol802354u

文献信息

• Catalyst-Controlled, Enantioselective, and Diastereodivergent Conjugate Addition of Aldehydes to Electron-Deficient Olefins
  作者：S. B. Jennifer Kan、Hiroki Maruyama、Matsujiro Akakura、Taichi Kano、Keiji Maruoka

  DOI：10.1002/anie.201705546

  日期：2017.8.1

  A chiral-amine-catalyzed enantioselective and diastereodivergent method for aldehyde addition to electron-deficient olefins is presented. Hydrogen bonding was used as a control element to achieve unusual anti selectivity, which was further elucidated through mechanistic and computational studies.

  提出了一种手性胺催化的对映选择性和非对映异构性的方法，用于将醛加成至缺电子烯烃中。氢键被用作控制元件以实现不同寻常的抗选择性，这通过机理和计算研究得到了进一步阐明。
• Organocatalytic Michael Addition of Aldehydes to γ-Keto-α,β-unsaturated Esters. An Efficient Entry to Versatile Chiral Building Blocks
  作者：Jing Wang、Anqi Ma、Dawei Ma

  DOI：10.1021/ol802354u

  日期：2008.12.4

  The diarylprolinol ether/HOAc-catalyzed Michael addition of aldehydes to gamma-keto-alpha,beta-unsaturated esters occurs in a highly regioselective and enantioselective manner. The adducts could easily be converted into synthetically useful cyclohexenones, cyclohexanones, piperidines, and gamma-lactones.