1-(1'-cyano-1'-carboethoxy)methylene-6-methoxy-1,2,3,4-tetrahydronaphthalene | 68254-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-(1'-cyano-1'-carboethoxy)methylene-6-methoxy-1,2,3,4-tetrahydronaphthalene
• 英文别名: ethyl [2-cyano-2-(6-methoxy-3,4-dihydronaphthalen-1-(2H)-ylidene)]acetate；ethyl cyano(6-methoxy-1,2,3,4-tetrahydro-1-naphthylidene)acetate；ethyl 2-cyano-2-(6-methoxy-3,4-dihydro-2H-naphthalen-1-ylidene)acetate
• CAS: 68254-77-3
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: SVZWBNSHBVLSDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(1'-cyano-1'-carboethoxy)methylene-6-methoxy-1,2,3,4-tetrahydronaphthalene 在 吡啶 、 氢氧化钾 、 copper(l) iodide 、 草酰氯 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙二醇 为溶剂， 反应 41.25h， 生成 (3SR)-1-diazo-3-<(1RS)-6-methoxy-1-methyl-1,2,3,4-tetrahydro-1-naphthyl>butan-2-one
  参考文献：
  名称：

  Mukhopadhyay, Chhanda; Ghosh, Soma; Mukherjee, Monika, Journal of Chemical Research, Miniprint, 1993, # 12, p. 3201 - 3219

  摘要：

  DOI：
• 作为产物：
  描述：

  氰乙酸乙酯 、 6-甲氧基-1-萘满酮 在 乙酸铵 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 7.0h， 以54%的产率得到1-(1'-cyano-1'-carboethoxy)methylene-6-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

• Synthesis and analgesic properties of some conformationally restricted analogs of profadol
  作者：Peter A. Crooks、Richard Szyndler

  DOI：10.1021/jm00180a021

  日期：1980.6

  N-Methylspiro[5-hydroxytetralin-1,3'-pyrrolidine] (2j) and N-methylspiro[7-hydroxytetralin-1,3'-pyrrolidine] (2n), conformationally restricted analogues of profadol, were synthesized via initial reaction of the appropriately substituted 1-tetralone with ethyl cyanoacetate to give the ethyl 1-tetralylidenecyanoacetate derivative (3), which was then reacted with KCN to give the corresponding 1-cyano

  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。
• Structure-activity studies of morphine fragments. III. Synthesis, opiate receptor binding, analgetic activity and conformational studies of spiro-[tetralin-1,4′-piperidines]
  作者：JA Lawson、L Toll、W Polgar、ET Uyeno、GH Loew

  DOI：10.1016/0223-5234(91)90003-6

  日期：1991.11

  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.
• Synthesis and biological evaluation of novel spiro 6-methoxytetralin-1,3′-pyrrolidine based organoselenocyanates against cadmium-induced oxidative and hepatic damage in mice
  作者：Ugir Hossain Sk、Arun K. Sharma、Sulekha Ghosh、Sudin Bhattacharya

  DOI：10.1016/j.ejmech.2010.04.001

  日期：2010.8

  A series of novel organoselenocyanate compounds (6a-d) having spiro[tetralin-1,3'-pyrrolidine] moiety were synthesized. The compounds were evaluated for their inhibitory activity against cadmium- (Cd) induced toxicity in Swiss Albino mice. All the compounds (6a-d) inhibited the level of lipid peroxidation (LPO) and upregulated the activity of glutathione-S-transferase (GST), superoxide dismutase (SOD), catalase (CAT) and reduced glutathione (GSH) levels in treatment group in comparison to the untreated Cd control group. Serum transaminase activities, e.g., alanine aminotransferase (ALT) and aspartate aminotransferase (AST) were also significantly lowered in the compound-treated mice. Elongation of the alkyl chain length bearing the selenocyanate (SeCN) active group enhanced the potency of the compounds, 6d being the most active one (6d > 6c > 6b > 6a). (C) 2010 Elsevier Masson SAS. All rights reserved.
• Mukhopadhyay, Chhanda; Ghosh, Soma; Mukherjee, Monika, Journal of Chemical Research, Miniprint, 1993, # 12, p. 3201 - 3219
  作者：Mukhopadhyay, Chhanda、Ghosh, Soma、Mukherjee, Monika、Mukherjee, Alok K.、Ghatak, Usha Ranjan

  DOI：——

  日期：——