(1'R,3'R)-2-(benzyloxycarbonylamino)-3-(3'-acetyl-2',2'-dimethylcyclobutyl)-(Z)-2-propenoic acid | 608536-60-3

• 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: (1'R,3'R)-2-(benzyloxycarbonylamino)-3-(3'-acetyl-2',2'-dimethylcyclobutyl)-(Z)-2-propenoic acid
• 英文别名: (Z)-3-[(1R,3R)-3-acetyl-2,2-dimethylcyclobutyl]-2-(phenylmethoxycarbonylamino)prop-2-enoic acid
• CAS: 608536-60-3
• 化学式: C₁₉H₂₃NO₅
• 分子量: 345.395
• InChiKey: JHVFHUXZCSMMFK-LTAXBSGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1'R,3'R)-2-(benzyloxycarbonylamino)-3-(3'-acetyl-2',2'-dimethylcyclobutyl)-(Z)-2-propenoic acid 在 1,2-bis[(2S,5S)-2,5-diethylphospholano]benzene(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate TEA 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、405.3 kPa 条件下， 反应 68.0h， 生成 (1'R,2S,3'R)-2-(benzyloxycarbonylamino)-3-(3'-acetyl-2',2'-dimethylcyclobutyl)propanoic acid N-[(S)-(benzyl)(methoxycarbonyl)methyl]amide
  参考文献：
  名称：

  Synthesis and diastereoselective catalytic hydrogenation of optically active cyclobutyl α,β-dehydro-α-dipeptides

  摘要：

  Optically active cyclobutyl (Z)-alpha, beta-dehydro-alpha-dipeptides have been efficiently synthesized through the coupling of conveniently protected glycine or (S)- phenylalanine residues with a (Z)-dehydro-alpha-amino acid derivative prepared, in turn, from (-)-verbenone as a chiral precursor. The alternative use of (R,R)- and (S,S)-Et-duphos-Rh as the hydrogenation catalyst led to the stereoselective production of both diastereomeric saturated dipeptides in each case. Thus, the chirality of the catalyst employed has been shown to be the factor governing the configuration of the newly created stereogenic centre. Regarding structural features, both NMR and CD data establish a marked conformational bias for both the unsaturated and the saturated peptides synthesized herein. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00485-3
• 作为产物：
  描述：

  methyl (1'R,3'R)-2-benzyloxycarbonylamino-3-[2',2'-dimethyl-3'-(2-methyl-1,3-dioxolan-2-yl)cyclobutyl]-(Z)-2-propenoate 在 potassium carbonate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 (1'R,3'R)-2-(benzyloxycarbonylamino)-3-(3'-acetyl-2',2'-dimethylcyclobutyl)-(Z)-2-propenoic acid
  参考文献：
  名称：

  Synthesis and diastereoselective catalytic hydrogenation of optically active cyclobutyl α,β-dehydro-α-dipeptides

  摘要：

  Optically active cyclobutyl (Z)-alpha, beta-dehydro-alpha-dipeptides have been efficiently synthesized through the coupling of conveniently protected glycine or (S)- phenylalanine residues with a (Z)-dehydro-alpha-amino acid derivative prepared, in turn, from (-)-verbenone as a chiral precursor. The alternative use of (R,R)- and (S,S)-Et-duphos-Rh as the hydrogenation catalyst led to the stereoselective production of both diastereomeric saturated dipeptides in each case. Thus, the chirality of the catalyst employed has been shown to be the factor governing the configuration of the newly created stereogenic centre. Regarding structural features, both NMR and CD data establish a marked conformational bias for both the unsaturated and the saturated peptides synthesized herein. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00485-3

文献信息

• Synthesis and diastereoselective catalytic hydrogenation of optically active cyclobutyl α,β-dehydro-α-dipeptides
  作者：Gemma P. Aguado、Albertina G. Moglioni、Beatriz N. Brousse、Rosa M. Ortuño

  DOI：10.1016/s0957-4166(03)00485-3

  日期：2003.8

  Optically active cyclobutyl (Z)-alpha, beta-dehydro-alpha-dipeptides have been efficiently synthesized through the coupling of conveniently protected glycine or (S)- phenylalanine residues with a (Z)-dehydro-alpha-amino acid derivative prepared, in turn, from (-)-verbenone as a chiral precursor. The alternative use of (R,R)- and (S,S)-Et-duphos-Rh as the hydrogenation catalyst led to the stereoselective production of both diastereomeric saturated dipeptides in each case. Thus, the chirality of the catalyst employed has been shown to be the factor governing the configuration of the newly created stereogenic centre. Regarding structural features, both NMR and CD data establish a marked conformational bias for both the unsaturated and the saturated peptides synthesized herein. (C) 2003 Elsevier Ltd. All rights reserved.