benzyl-2-oxo-tetradecanoate | 193957-71-0

• 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: benzyl-2-oxo-tetradecanoate
• 英文别名: Benzyl 2-oxotetradecanoate
• CAS: 193957-71-0
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: HATIZZIYFATALN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  benzyl-2-oxo-tetradecanoate 在 palladium on activated charcoal Ti(OiPr)Cl3 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 水 、 三氟乙酸 为溶剂， 反应 13.67h， 生成 (+)-cinatrin C1
  参考文献：
  名称：

  Aldol reactions of ketal-protected tartrate ester enolates. Asymmetric syntheses and absolute stereochemical assignments of phospholipase A2 inhibitors cinatrin C1 and C3

  摘要：

  An efficient approach to the syntheses of cinatrins C-1 and C-3 has been developed and used to establish the absolute configurations of these natural products. The construction of each molecule has been achieved in a five-step reaction sequence (overall yield 43% for cinatrin C-1, 33% for cinatrin C-3) from the di-tert-butyl ester of (R,R)-tartaric acid. The two contiguous, quaternary chiral centers in the cinatrin skeleton are constructed via a diastereoselective, titanium-mediated aldol coupling of a tartrate-derived silylketene acetal and an achiral alpha-ketoester. This bond construction proceeds with excellent diastereoselectivity for a variety of aldehyde and alpha-ketoester substrates. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)90390-2
• 作为产物：
  描述：

  肉豆蔻酸苄酯 在 草酰氯 、 双(三甲基硅烷基)氨基钾 、 二甲基亚砜 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 benzyl-2-oxo-tetradecanoate
  参考文献：
  名称：

  Aldol reactions of ketal-protected tartrate ester enolates. Asymmetric syntheses and absolute stereochemical assignments of phospholipase A2 inhibitors cinatrin C1 and C3

  摘要：

  An efficient approach to the syntheses of cinatrins C-1 and C-3 has been developed and used to establish the absolute configurations of these natural products. The construction of each molecule has been achieved in a five-step reaction sequence (overall yield 43% for cinatrin C-1, 33% for cinatrin C-3) from the di-tert-butyl ester of (R,R)-tartaric acid. The two contiguous, quaternary chiral centers in the cinatrin skeleton are constructed via a diastereoselective, titanium-mediated aldol coupling of a tartrate-derived silylketene acetal and an achiral alpha-ketoester. This bond construction proceeds with excellent diastereoselectivity for a variety of aldehyde and alpha-ketoester substrates. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)90390-2

文献信息

• Aldol reactions of ketal-protected tartrate ester enolates. Asymmetric syntheses and absolute stereochemical assignments of phospholipase A2 inhibitors cinatrin C1 and C3
  作者：David A. Evans、B. Wesley Trotter、James C. Barrow

  DOI：10.1016/s0040-4020(97)90390-2

  日期：1997.6

  An efficient approach to the syntheses of cinatrins C-1 and C-3 has been developed and used to establish the absolute configurations of these natural products. The construction of each molecule has been achieved in a five-step reaction sequence (overall yield 43% for cinatrin C-1, 33% for cinatrin C-3) from the di-tert-butyl ester of (R,R)-tartaric acid. The two contiguous, quaternary chiral centers in the cinatrin skeleton are constructed via a diastereoselective, titanium-mediated aldol coupling of a tartrate-derived silylketene acetal and an achiral alpha-ketoester. This bond construction proceeds with excellent diastereoselectivity for a variety of aldehyde and alpha-ketoester substrates. (C) 1997 Elsevier Science Ltd.