反式-2-羟基-3-硝基肉桂酸乙酯 | 86981-10-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 反式-2-羟基-3-硝基肉桂酸乙酯
• 英文名称: ethyl trans-2-hydroxy-3-nitrocinnamate
• 英文别名: ethyl (E)-3-(2-hydroxy-3-nitrophenyl)prop-2-enoate
• CAS: 86981-10-4
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: ZFODYTUMAHNITH-VOTSOKGWSA-N

物化性质

• 沸点：
  353.5±32.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  反式-2-羟基-3-硝基肉桂酸乙酯 在 palladium on activated charcoal palladium diacetate 、 lithium aluminium tetrahydride 、 草酰氯 、 氢气 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 xylene 为溶剂， 生成 (1R,2R)-2-(2-Ethylbenzo[d]oxazol-7-yl)cyclopropanecarbaldehyde
  参考文献：
  名称：

  Design and synthesis of benzoxazole derivatives as novel melatoninergic ligands

  摘要：

  A novel series of benzoxazole derivatives was synthesized and evaluated as melatoninergic ligands. The binding affinity of these compounds for human MT1 and MT2 receptors was determined using 2-[I-125]-iodomelatonin as the radioligand. The results of the SAR studies in this series led to the identification of compound 28, which exhibited better MT1 and MT2 receptor affinities than melatonin itself. This work also established the benzoxazole nucleus as a melatoninergic pharmacophore, which served as an isosteric replacement to the previously established alkoxyaryl core. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.052
• 作为产物：
  描述：

  3-硝基水杨醛 、 乙氧甲酰基亚甲基三苯基膦 以 四氢呋喃 为溶剂， 以90%的产率得到反式-2-羟基-3-硝基肉桂酸乙酯
  参考文献：
  名称：

  Design and synthesis of benzoxazole derivatives as novel melatoninergic ligands

  摘要：

  A novel series of benzoxazole derivatives was synthesized and evaluated as melatoninergic ligands. The binding affinity of these compounds for human MT1 and MT2 receptors was determined using 2-[I-125]-iodomelatonin as the radioligand. The results of the SAR studies in this series led to the identification of compound 28, which exhibited better MT1 and MT2 receptor affinities than melatonin itself. This work also established the benzoxazole nucleus as a melatoninergic pharmacophore, which served as an isosteric replacement to the previously established alkoxyaryl core. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.052

文献信息

• Convenient Synthesis of a Simple Coumarin from Salicylaldehyde and Wittig Reagent (III): Synthesis of Nitrocoumarins
  作者：Takashi Harayama、Kazumitsu Nakatsuka、Hiromi Nishioka、Kyoko Murakami、Yukiko Ohmori、Yasuo Takeuchi、Hisashi Ishii、Kazuhiro Kenmotsu

  DOI：10.3987/com-94-6910

  日期：——

  Reaction of nitrosalicylaldehydes (1) with carbethoxymethylenetriphenylphosphorane in Et(2)NPh, in Ph(2)O, and in the absence of solvent (neat) at 210-215 degrees C was investigated. Reaction of 3-nitrosalicylaldehyde (1d) in Et(2)NPh afforded the benzoxazole (6) and the aminocoumarin (3e) along with the expected coumarin (3d). It was clarified that the origin of carbon-unit introduced for the formation of the benzoxazole ring came from the alkyl group of solvent.
• Valizadeh; Shockravi; Heravi, Journal of Chemical Research - Part S, 2003, # 11, p. 718 - 720
  作者：Valizadeh、Shockravi、Heravi、Ghadim, H. Abbasi

  DOI：——

  日期：——
• Design and synthesis of benzoxazole derivatives as novel melatoninergic ligands
  作者：Li-Qiang Sun、Jie Chen、Katherine Takaki、Graham Johnson、Lawrence Iben、Cathy D. Mahle、Elaine Ryan、Cen Xu

  DOI：10.1016/j.bmcl.2003.12.052

  日期：2004.3

  A novel series of benzoxazole derivatives was synthesized and evaluated as melatoninergic ligands. The binding affinity of these compounds for human MT1 and MT2 receptors was determined using 2-[I-125]-iodomelatonin as the radioligand. The results of the SAR studies in this series led to the identification of compound 28, which exhibited better MT1 and MT2 receptor affinities than melatonin itself. This work also established the benzoxazole nucleus as a melatoninergic pharmacophore, which served as an isosteric replacement to the previously established alkoxyaryl core. (C) 2003 Elsevier Ltd. All rights reserved.