4-甲氧基肉桂基异氰酸酯 | 101033-24-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-甲氧基肉桂基异氰酸酯
• 英文名称: 4-methoxycinnamyl isocyanate
• 英文别名: p-methoxystyryl isocyanate；p-Methoxycinnamoyl-isocyanat；1-[(E)-2-isocyanatoethenyl]-4-methoxybenzene
• CAS: 101033-24-3
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: FLHKJAOGWRSYGF-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲氧基肉桂基异氰酸酯 在 palladium on activated charcoal 氢气 、 碘 作用下， 以 乙醇 、 邻二氯苯 为溶剂， 80.0 ℃ 、413.69 kPa 条件下， 反应 48.0h， 生成 7-甲氧基-3,4-二氢-2H-异喹啉-1-酮
  参考文献：
  名称：

  Ajao, J. F.; Bird, C. W., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 329 - 331

  摘要：

  DOI：
• 作为产物：
  描述：

  反式-4-甲氧基肉桂酸 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 benzine 、 甲苯 为溶剂， 反应 3.0h， 生成 4-甲氧基肉桂基异氰酸酯
  参考文献：
  名称：

  N-(苯乙烯基氨基甲酰基)乙酸乙酯的热诱导二聚环化：4-羟基-2(1H)-吡啶酮-3-甲酰胺衍生物的形成

  摘要：

  摘要 已经研究了 N-（苯乙烯基氨基甲酰基）乙酸乙酯衍生物的热诱导二聚环化，导致 4-羟基-2（1H）-吡啶酮-3-甲酰胺衍生物在二苯醚中在 200-210 °C 下具有良好的产率。N-(苯乙烯基氨基甲酰基)乙酸乙酯衍生物在二甲苯中回流时容易提供分子间环化产物4-羟基-2(1H)-吡啶酮-3-羧酸酯。此外，还制备了几种相关的 3-acetyl-4-hydroxy-5-phenylpyridin-2(1H)-ones。它提供了 4-羟基-2(1H)-吡啶酮-3-甲酰胺衍生物的有效制备方法。图形概要

  DOI：

  10.1080/00397911.2013.878360

文献信息

• Discovery of Potent, Selective, Orally Active, Nonpeptide Inhibitors of Human Mast Cell Chymase
  作者：Michael N. Greco、Michael J. Hawkins、Eugene T. Powell、Harold R. Almond,、Lawrence de Garavilla、Jeffrey Hall、Lisa K. Minor、Yuanping Wang、Thomas W. Corcoran、Enrico Di Cera、Angelene M. Cantwell、Savvas N. Savvides、Bruce P. Damiano、Bruce E. Maryanoff

  DOI：10.1021/jm0700619

  日期：2007.4.1

  identified as a new structural motif for obtaining potent inhibitors of human mast cell chymase. For example, 1-naphthyl derivative 5f had an IC50 value of 29 nM and (E)-styryl derivative 6g had an IC50 value of 3.5 nM. An X-ray structure for 5f.chymase revealed key interactions within the enzyme active site. Compound 5f was selective for inhibiting chymase versus eight serine proteases. Compound 6h

  一系列的β-羧酰胺基膦酸（in）酸（2）被确定为获得有效的人肥大细胞糜酶抑制剂的新结构基序。例如，1-萘基衍生物5f的IC 50值为29nM，（E）-苯乙烯基衍生物6g的IC 50值为3.5nM。5f.chymase的X射线结构揭示了酶活性位点内的关键相互作用。与8种丝氨酸蛋白酶相比，化合物5f对抑制糜蛋白酶具有选择性。化合物6h在大鼠中可口服生物利用（F ＝ 39％），并且在仓鼠炎症模型中口服有效。
• Cycloaddition reactions of carbodiimides. The first example of an intramolecular Diels–Alder reaction of CC-conjugated carbodiimides
  作者：Pedro Molina、Mateo Alajarín、Angel Vidal

  DOI：10.1039/c39900001277

  日期：——

  An one-pot preparation of α-carbolines and quinindolines from conjugated carbodiimides based on a tandem Intramolecular Diels–Alder cycloaddition/oxidative aromatization is described.

  描述了一种基于串联的分子内Diels-Alder环加成/氧化芳构化反应的共轭碳二亚胺单罐制备α-咔啉和喹啉的方法。
• Non-natural nucleotides and dinucleotides
  申请人：——

  公开号：US20040122223A1

  公开（公告）日：2004-06-24

  Nucleotide derivatives of formula (1) are described: wherein: G is a hydrogen atom or an optionally substituted aliphatic, heteroaliphatic, cycloaliphatic, polycycloaliphatic, aromatic or heteroaromatic group or a non-natural nucleoside as defined herein; G′ is a non-natural necleoside as defined herein; n is zero, or the integer 1 or 2; m is zero or the integer 1 or 2; and the salts, solvates, hydrates and N-oxides thereof. The compounds are P2Y receptor agonists and are of use in the prophylaxis and treatment of diseases and disorders involving abnormal secretory mechanisms such as inadequate functioning of mucociliary clearance mechanisms or abnormal tear secretion or in the treatment of diseases involving inappropriate cellular glucose uptake.

  公式（1）的核苷酸衍生物被描述如下：其中：G是氢原子或可选择取代的脂肪，杂脂肪，环脂肪，多环脂肪，芳香或杂芳基团或非天然核苷酸，如此处所定义；G'是如此处所定义的非天然核苷酸；n为零或整数1或2；m为零或整数1或2；以及其盐，溶剂化合物，水合物和N-氧化物。这些化合物是P2Y受体激动剂，用于预防和治疗涉及异常分泌机制的疾病和障碍，如粘液纤毛清除机制功能不足或泪液分泌异常，或用于治疗涉及不适当的细胞葡萄糖摄取的疾病。
• C=C-conjugated carbodiimides as 2-aza dienes in intramolecular [4+2] cycloadditions. One-pot preparation of quinoline, .alpha.-carboline, and quinindoline derivatives
  作者：Pedro Molina、Mateo Alajarin、Angel Vidal、Pilar Sanchez-Andrada

  DOI：10.1021/jo00029a026

  日期：1992.1

  Iminophosphoranes 2 derived from o-aminostyrenes react with aryl isocyanates to give the corresponding carbodiimides 13 which by thermal treatment at 160-degrees-C undergo 6-pi-electrocyclization to give quinoline derivatives 14. However, the reaction with styryl isocyanates leads to alpha-carbolines 19 through the intermediate carbodiimides 15 which undergo a tandem intramolecular hetero-Diels-Alder cycloaddition/aromatization process to give 19. Similarly, related alpha-carbolines 20-22 can be obtained from the reaction of iminophosphoranes derived from ortho-substituted anilines containing an unsaturated side chain with styryl isocyanates. Iminophosphorane 6a, derived from o-butadienylaniline, and related 10 and 12 react with aryl isocyanates under the same reaction conditions to give quinindoline derivatives 25-27, respectively. Finally, iminophosphoranes 2 and 6 by reaction with ketenes lead directly to quinolines 32 and benzo[b]carbazoles 33, respectively.
• Vinyl isocyanates as aza diene equivalents. A method for the synthesis of functionalized 4-hydroxy-2(1H)-pyridones
  作者：James H. Rigby、Frederick J. Burkhardt

  DOI：10.1021/jo00358a046

  日期：1986.4