Methyl 6-phthalimidohex-2-enoate | 19991-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: Methyl 6-phthalimidohex-2-enoate
• 英文别名: 6-phthalimido-hex-2-enoic acid methyl ester；6-phthalimido-hex-2t-enoic acid methyl ester；6-Phthalimido-hex-2t-ensaeure-methylester；6-Phthalimido-hexen-(2)-saeure-methylester；methyl (E)-6-(1,3-dioxoisoindol-2-yl)hex-2-enoate
• CAS: 19991-87-8
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: WPYWOAFRDGIHBM-YCRREMRBSA-N

物化性质

• 沸点：
  415.2±38.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 6-phthalimidohex-2-enoate 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 K₂Os(OH)3 、 三氟化硼乙醚 、 氢气 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 、 叔丁醇 为溶剂， 反应 38.0h， 生成 Methyl (2S,3R)-3-(benzyloxy)-2-<(tert-butyloxycarbonyl)amino>-6-phthalimidohexanoate
  参考文献：
  名称：

  Two Chiral Syntheses of threo-3-Hydroxylsine

  摘要：

  Two efficient chiral syntheses of 3-hydroxylysine, a naturally occurring amino acid and a putative intermediate in the synthesis of balanol, a potent protein kinase C inhibitor, are described. The synthesis of (2R,3S)-3-hydroxylysine utilizes Hayashi's chiral ferroceno gold catalyst. The synthesis of (2S,3R)-3-hydroxylysine demonstrates a beta-hydroxy amino acid synthesis with the chirality derived from the Sharpless chiral cis-hydroxylation.

  DOI：

  10.1021/jo00098a047
• 作为产物：
  描述：

  2-bromo-5-phthalimido-valeric acid 在 氯化亚砜 、 silver(l) oxide 作用下， 生成 Methyl 6-phthalimidohex-2-enoate
  参考文献：
  名称：

  Über die Wolffsche Umlagerung von 1-Diazo-3-brom-ω-phthalimido-alkanonen-(2)

  摘要：

  DOI：

  10.1007/bf00905669

文献信息

• Phthalimides as Exceptionally Efficient Single Electron Transfer Acceptors in Reductive Coupling Reactions Promoted by Samarium Diiodide
  作者：Tatiana Vacas、Eleuterio Álvarez、Jose Luis Chiara

  DOI：10.1021/ol7023357

  日期：2007.12.1

  shows that phthalimides are highly efficient single electron transfer acceptors in reactions promoted by samarium diiodide, affording ketyl radical anion intermediates, which participate in high-yielding inter- and intramolecular reductive coupling processes with different radicophiles including imides, oxime ethers, nitrones, and Michael acceptors.

  实验和理论证据表明，邻苯二甲酰亚胺是二碘化sa促进的反应中的高效单电子转移受体，提供酮基自由基阴离子中间体，该中间体与不同的亲二酮体（包括酰亚胺，肟醚，硝酮）参与高产分子间和分子内的还原偶联过程。以及Michael的接受者。
• Biochemical Synthesis of 6-Amino Caproic Acid
  申请人：Raemakers-Franken C. Petronella

  公开号：US20070254341A1

  公开（公告）日：2007-11-01

  The invention relates to biochemical synthesis of 6-amino caproic acid from 6-aminohex-2-enoic acid compound or from 6-amino-2-hydroxyhexanoic acid, by treatment with an enzyme having α,β-enoate reductase activity towards molecules containing an α,β-enoate group and a primary amino group. The invention also relates to processes for obtaining suitable genetically engineered cells for being used in such biotransformation process, and to precursor fermentation of 6-amino caproic acid from intermediates leading to 6-amino caproic acid. Finally, the invention relates to certain novel biochemically produced compounds, namely 6-aminohex-2-enoic acid, 6-aminohexanoic acid, as well as to caprolactam produced therefrom and to nylon-6 and other derivatives produced from such biochemically produced compounds or caprolactam.

  本发明涉及通过用具有α，β-烯酸还原酶活性的酶处理含有α，β-烯酸基团和一级氨基团分子的6-氨基己-2-烯酸化合物或6-氨基-2-羟基己酸，从而生物化学合成6-氨基己酸。本发明还涉及用于此类生物转化过程的适用的基因工程细胞的获得过程，以及从导致6-氨基己酸的中间体中进行的前体发酵。最后，本发明涉及某些新型生物化学合成的化合物，即6-氨基己-2-烯酸、6-氨基己酸，以及由此产生的己内酰胺和从这样的生物化学合成的化合物或己内酰胺产生的尼龙-6和其他衍生物。
• Biochemical synthesis of 6-amino caproic acid
  申请人：Raemakers-Franken Petronella C.

  公开号：US20090137759A1

  公开（公告）日：2009-05-28

  The invention relates to biochemical synthesis of 6-amino caproic acid from 6-aminohex-2-enoic acid compound or from 6-amino-2-hydroxyhexanoic acid, by treatment with an enzyme having α,β-enoate reductase activity towards molecules containing an α,β-enoate group and a primary amino group. The invention also relates to processes for obtaining suitable genetically engineered cells for being used in such biotransformation process, and to precursor fermentation of 6-amino caproic acid from intermediates leading to 6-amino caproic acid. Finally, the invention relates to certain novel biochemically produced compounds, namely 6-aminohex-2-enoic acid, 6-aminohexanoic acid, as well as to caprolactam produced therefrom and to nylon-6 and other derivatives produced from such biochemically produced compounds or caprolactam.

  本发明涉及从6-氨基己-2-烯酸化合物或从6-氨基-2-羟基己酸经由酶处理，该酶具有对含有α，β-烯酸基团和一级氨基的分子具有α，β-烯酸还原酶活性的生物化学合成6-氨基己酸的方法。本发明还涉及获得适用于此类生物转化过程的合适基因工程细胞的方法以及从导致6-氨基己酸的中间体中的前体发酵。最后，本发明涉及某些新型的生物化学合成的化合物，即6-氨基己-2-烯酸，6-氨基己酸，以及从中生产的己内酰胺和从这些生物化学合成化合物或己内酰胺生产的尼龙6和其他衍生物。
• Biochemical synthesis of 6 amino caproic acid
  申请人：DSM IP Assets B.V.

  公开号：EP2194139A1

  公开（公告）日：2010-06-09

  The invention relates to biochemical synthesis of 6-amino caproic acid from 6-aminohex-2-enoic acid compound or from 6-amino-2-hydroxyhexanoic acid, by treatment with an enzyme having α,β-enoate reductase activity towards molecules containing an α,β-enoate group and a primary amino group. The invention also relates to processes for obtaining suitable genetically engineered cells for being used in such biotransformation process, and to precursor fermentation of 6-amino caproic acid from intermediates leading to 6-amino caproic acid. Finally, the invention relates to certain novel biochemically produced compounds, namely 6-aminohex-2-enoic acid, 6-aminohexanoic acid, as well as to caprolactam produced therefrom and to nylon-6 and other derivatives produced from such biochemically produced compounds or caprolactam.

  本发明涉及以 6-氨基己-2-烯酸化合物或 6-氨基-2-羟基己酸为原料，通过对含有 α，β-烯酸基和伯氨基的分子具有 α，β-烯酸还原酶活性的酶处理，生化合成 6-氨基己酸。 本发明还涉及获得用于这种生物转化过程的合适基因工程细胞的过程，以及从导致 6-氨基己酸的中间产物中发酵 6-氨基己酸的前体。 最后，本发明涉及某些新型生化生产的化合物，即 6-氨基己-2-烯酸、6-氨基己酸，以及由其生产的己内酰胺和由这种生化生产的化合物或己内酰胺生产的尼龙-6 和其他衍生物。
• BIOCHEMICAL SYNTHESIS OF 6-AMINO CAPROIC ACID
  申请人：DSM IP Assets B.V.

  公开号：EP1706501B1

  公开（公告）日：2010-01-13