(2S)-pent-4-enoic acid [2-methoxycarbonyl-2-(pent-4-enoylamino)]ethyl ester | 957278-69-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-pent-4-enoic acid [2-methoxycarbonyl-2-(pent-4-enoylamino)]ethyl ester
• 英文别名: [(2S)-3-methoxy-3-oxo-2-(pent-4-enoylamino)propyl] pent-4-enoate
• CAS: 957278-69-2
• 化学式: C₁₄H₂₁NO₅
• 分子量: 283.324
• InChiKey: FLJKZOPAQJCUHM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-pent-4-enoic acid [2-methoxycarbonyl-2-(pent-4-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45%的产率得到(3R)-5,12-dioxo-1-oxa-4-azacyclodec-8-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
• 作为产物：
  描述：

  4-戊烯酸 、 L-丝氨酸甲酯盐酸盐 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以59%的产率得到(2S)-pent-4-enoic acid [2-methoxycarbonyl-2-(pent-4-enoylamino)]ethyl 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

文献信息

• A Strategy for Macrocyclic Ring Closure and Functionalization Aimed toward Split-Pool Syntheses
  作者：Daesung Lee、Jason K. Sello、Stuart L. Schreiber

  DOI：10.1021/ja992658m

  日期：1999.11.1
• Cross-metathesis and ring-closing metathesis reactions of amino acid-based substrates
  作者：Andrea J. Vernall、Steven Ballet、Andrew D. Abell

  DOI：10.1016/j.tet.2008.02.043

  日期：2008.4

  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.