1-(1'-cyano-1'-carboethoxy)methylene-7-methoxy-1,2,3,4-tetrahydronaphthalene | 139157-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(1'-cyano-1'-carboethoxy)methylene-7-methoxy-1,2,3,4-tetrahydronaphthalene
• 英文别名: 2-cyano-2-(2,3-dihydro-6-methoxy naphthalen-4(1H)-ylidene) acetic acid
• CAS: 139157-83-8
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: AXFCDKMPWRHLNS-UHFFFAOYSA-N

物化性质

• 沸点：
  436.8±45.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.32
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(1'-cyano-1'-carboethoxy)methylene-7-methoxy-1,2,3,4-tetrahydronaphthalene 在 platinum(IV) oxide 氢气 、 溶剂黄146 、 lithium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 24.5h， 生成
  参考文献：
  名称：

  Structure-activity studies of morphine fragments. III. Synthesis, opiate receptor binding, analgetic activity and conformational studies of spiro-[tetralin-1,4′-piperidines]

  摘要：

  A series of 5 spiro compounds, a new class of conformationally restricted analogs of 4-alkyl-4-(m-OH-phenyl) piperidines, have been synthesized and their affinities for mu, delta and kappa-opioid receptor sites and in vivo analgetic activities determined. All compounds show rather low affinities for the 3 receptors, with some modulation by the N-substituent and by the position of the phenolic group. To help understand the origin of this poor affinity compared to the unrestricted 4-alkyl-4-phenyl piperidines, energy conformation calculations were performed which indicated that all the analogs favor a phenyl equatorial over a phenyl axial conformer. Significant differences in the lowest energy conformation were found between these spiro analogs and both morphine and 4-n-propyl-4-(m-OH-phenyl) piperidines, 18 and 19 which are conformationally unrestricted, closely related analogs with high mu-affinity. These differences could account for their lower affinities. To continue the search for more active members of the family, structure variations which favor a phenyl-axial conformation have been identified and proposed for further study.

  DOI：

  10.1016/0223-5234(91)90003-6
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 、 氰乙酸乙酯 在 乙酸铵 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 7.0h， 以52%的产率得到1-(1'-cyano-1'-carboethoxy)methylene-7-methoxy-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  普萘洛尔某些构象受限的类似物的合成和止痛特性。

  摘要：

  N-甲基螺基[5-羟基四氢-1,3'-吡咯烷]（2j）和N-甲基螺基[7-羟基四氢-1,3'-吡咯烷]（2n），是异丙酚的构象受限类似物，是通过以下方法合成的：用氰基乙酸乙酯适当取代的1-四氢萘酮，得到1-四亚乙基氰基乙酸乙酯衍生物（3），然后使其与KCN反应，得到相应的1-氰基-1-（氰甲基）四氢化萘（4）。在干燥的乙醚-二氯甲烷或乙酸-硫酸中用HBr处理4，得到螺[tetralin-1,3'-吡咯烷-2'，5'-二酮]衍生物（5），然后将其用LiAlH4-还原THF并用HCHO-HCO2H N-甲基化，得到适当取代的螺[tetralin-1,3'-吡咯烷]（2）。在热板试验和扭体试验中，2j和2n以及异构体6-羟基衍生物21均未显示出明显的镇痛活性。然而，螺[tetralin-1,3'-pyrrolidine]（2a）及其N-甲基衍生物（2b）都具有可待因水平的镇痛活性。

  DOI：

  10.1021/jm00180a021

文献信息

• A Simple and Efficient Procedure for Synthesis of Agomelatine
  作者：G. Gurunadham、R. Madhusudhan Raju、Y. Venkateswarlu

  DOI：10.14233/ajchem.2016.19712

  日期：——

  A simple and efficient process for the large scale preparation of agomelatine, an antidepressant drug is described. Agomelatine was synthesized from 7-methoxy-1-tetralone in five steps. The route reported employs readily, commercially viable starting materials, reagents and potentially be utilized for the process of synthesis of agomelatine.

  本文介绍了一种大规模制备抗抑郁药物阿戈美拉汀的简单而高效的工艺。阿戈美拉汀由 7-甲氧基-1-四氢萘酮经五个步骤合成。所报告的路线采用了易于商业化的起始材料和试剂，有可能用于阿戈美拉汀的合成过程。