(3R)-5,24-dioxo-1-oxa-4-azacyclotetracos-14-ene-3-carboxylic acid methyl ester | 1028203-55-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (3R)-5,24-dioxo-1-oxa-4-azacyclotetracos-14-ene-3-carboxylic acid methyl ester
• CAS: 1028203-55-5
• 化学式: C₂₄H₄₁NO₅
• 分子量: 423.593
• InChiKey: OJUPJGWSKUIXTF-ATKOVBFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  30.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (2S)-undec-10-enoic acid [2-methoxycarbonyl-2-(undec-10-enoylamino)]ethyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以15%的产率得到(3R)-5,24-dioxo-1-oxa-4-azacyclotetracos-14-ene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Cross-metathesis and ring-closing metathesis reactions of amino acid-based substrates

  摘要：

  Olefin tethers of variable length, introduced into a natural amino acid (side-chain of Ser, Cys; N-terminus of Arg; C-terminus of Phe and Tic; and in both the side-chain and either the N- or C-terminus of Ser, Cys and Tyr), undergo metathesis on treatment with Grubbs' second generation catalyst. Side-chain linked dimers of Ser, Cys and Tyr were obtained by cross-metathesis, while olefin installation at the N- and C-terminus led to dimers of Arg and Phe (or Tic), respectively. Ring-closing metathesis of the doubly alkenylated derivatives of Ser, Cys and Tyr gave 12-, 20- and 24-membered macrocycles. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.043