(1S,4R)-4-(甲氧羰基)-2-环丁烯-1-羧酸 | 151715-95-6

• 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
• 中文名称: (1S,4R)-4-(甲氧羰基)-2-环丁烯-1-羧酸
• 英文名称: methyl hydrogen (1R,2S)-(+)-3-cyclobutene-1,2-dicarboxylate
• 英文别名: (1S,4R)-4-methoxycarbonylcyclobut-2-ene-1-carboxylic acid
• CAS: 151715-95-6
• 化学式: C₇H₈O₄
• 分子量: 156.138
• InChiKey: MTWLXSDEHFKHPV-CRCLSJGQSA-N

物化性质

• 沸点：
  273.0±40.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	cis-dimethyl cyclobutene-3,4-dicarboxylate	42577-15-1	C8H10O4	170.165
  ——	Cyclobut-3-en-1,2-dicarbonsaeuredimethylester	60333-14-4	C8H10O4	170.165
  ——	cis-3-cyclobutene-1,2-dicarboxylic anhydride	10374-07-9	C6H4O3	124.096

反应信息

• 作为反应物：
  描述：

  (1S,4R)-4-(甲氧羰基)-2-环丁烯-1-羧酸 以 氘代氯仿 为溶剂， 反应 0.05h， 生成 methyl (1R,2S)-(+)-2-benzylcarbamoyl-3-cyclobutene carboxylate
  参考文献：
  名称：

  Enzymatic hydrolysis of meso-cyclobutene esters.

  摘要：

  Dimethyl cis-2-cyclobutene-1,2-carboxylate 1 was kinetically resolved by porcine liver esterase to give methyl hydrogen (1R,2S)- (+)-cis- 3-cyclobutene-1,2-dicarboxylate 3. ((1R,4S)-4-Ethanoyloxymethyl-2-cyclobutenyl)methyl ethanoate 2 was kinetically resolved using the lipase from Pseudomonas fluorescens (Amano P) to give ((1R,4S)-4-hydroxymethyl-2-cyclobutenyl)methyl ethanoate 8.

  DOI：

  10.1016/s0957-4166(00)80118-4
• 作为产物：
  描述：

  Cyclobut-3-en-1,2-dicarbonsaeuredimethylester 生成 (1S,4R)-4-(甲氧羰基)-2-环丁烯-1-羧酸
  参考文献：
  名称：

  LUKAS, KARL-LUDWIG

  摘要：

  DOI：

文献信息

• Efficient total synthesis of racemic and optically active cyclobut-A and simple analogues
  作者：Michael E. Jung、Adam W. Sledeski

  DOI：10.1039/c39930000589

  日期：——

  Rapid synthesis of the potent antiviral agent, cyclobut-A, 1a, from the inexpensive starting materials maleic anhydride and acetylene, in both racemic and optically active forms, is described; the route also allows for the preparation of several hydroxylated and keto analogues in good overall yield.

  本文介绍了从廉价的马来酸酐和乙炔为起始原料快速合成外消旋和光学活性形式的强效抗病毒剂环丁-A 1a的方法；该方法还能以良好的总收率制备多种羟基和酮类似物。
• Total Synthesis and Bioactivity of Resolvin E2
  作者：Seiji Ogawa、Daisuke Urabe、Yoshiyuki Yokokura、Hiroyuki Arai、Makoto Arita、Masayuki Inoue

  DOI：10.1021/ol901350g

  日期：2009.8.20

  Resolvin E2 is a potent anti-inflammatory compound, derived from eicosapentaenoic acid. The efficient total synthesis of resolvin E2 by taking advantage of its intrinsic pseudoenantiomeric substructures is reported. The synthetic resolvin E2 proved to be biologically active in blocking neutrophil Infiltration and reducing proinflammatory cytokines in the acute peritonitis model.
• LUKAS, KARL-LUDWIG
  作者：LUKAS, KARL-LUDWIG

  DOI：——

  日期：——
• Enzymatic hydrolysis of meso-cyclobutene esters.
  作者：Ian Harvey、David H.G. Crout

  DOI：10.1016/s0957-4166(00)80118-4

  日期：1993.5

  Dimethyl cis-2-cyclobutene-1,2-carboxylate 1 was kinetically resolved by porcine liver esterase to give methyl hydrogen (1R,2S)- (+)-cis- 3-cyclobutene-1,2-dicarboxylate 3. ((1R,4S)-4-Ethanoyloxymethyl-2-cyclobutenyl)methyl ethanoate 2 was kinetically resolved using the lipase from Pseudomonas fluorescens (Amano P) to give ((1R,4S)-4-hydroxymethyl-2-cyclobutenyl)methyl ethanoate 8.

表征谱图