2-(2-(3,4-二氢萘基))-2-甲基丙酸乙酯 | 100820-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-(2-(3,4-二氢萘基))-2-甲基丙酸乙酯
• 英文名称: ethyl 2-(2-<3,4-dihydronaphthalenyl>)-2-methylpropanoate
• 英文别名: ethyl 2-(3,4-dihydro-2-naphthalenyl)-2-methylpropanoate；Ethyl 2-(3,4-dihydronaphthalen-2-yl)-2-methylpropanoate
• CAS: 100820-31-3
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: VQLHULDUPXQQOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(2-(3,4-二氢萘基))-2-甲基丙酸乙酯 在 lithium aluminium tetrahydride 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(2-<3,4-dihydronaphthalenyl>)-2-methylpropanal
  参考文献：
  名称：

  通过氮杂-二-π-甲烷重排光化学合成1-碳杂双环[n.1.0]烷烃的肟肟酸酯衍生物。

  摘要：

  某些1-碳杂双环[n.1.0]烷烃肟乙酸酯的第一个光化学合成是通过2-（环戊-1-烯基）-和2-的乙酸肟酯的氮杂-二-π-甲烷（ADPM）重排而实现的。 （环己-1-烯基）-2-甲基丙醛。环尺寸的进一步增加不利地影响该反应，并且2-（环庚-1-烯基）-2-甲基丙醛的肟肟乙酸酯通过ADPM途径不反应。通过引入苯并取代基和该化合物2-（2- [2- [3,4-二氢萘基]）-2-甲基丙醛，可以克服2-（环己-1-烯基）-2-甲基丙醛的重排效率低的问题，有效地进行ADPM重排。

  DOI：

  10.1016/s0040-4020(01)87986-2
• 作为产物：
  描述：

  ethyl 2-(2-hydroxy-3,4-dihydro-1H-naphthalen-2-yl)-2-methylpropanoate 在 phosphorus pentoxide 作用下， 以 苯 为溶剂， 反应 3.0h， 以92%的产率得到2-(2-(3,4-二氢萘基))-2-甲基丙酸乙酯
  参考文献：
  名称：

  通过氮杂-二-π-甲烷重排光化学合成1-碳杂双环[n.1.0]烷烃的肟肟酸酯衍生物。

  摘要：

  某些1-碳杂双环[n.1.0]烷烃肟乙酸酯的第一个光化学合成是通过2-（环戊-1-烯基）-和2-的乙酸肟酯的氮杂-二-π-甲烷（ADPM）重排而实现的。 （环己-1-烯基）-2-甲基丙醛。环尺寸的进一步增加不利地影响该反应，并且2-（环庚-1-烯基）-2-甲基丙醛的肟肟乙酸酯通过ADPM途径不反应。通过引入苯并取代基和该化合物2-（2- [2- [3,4-二氢萘基]）-2-甲基丙醛，可以克服2-（环己-1-烯基）-2-甲基丙醛的重排效率低的问题，有效地进行ADPM重排。

  DOI：

  10.1016/s0040-4020(01)87986-2

文献信息

• Novel Photoreactions of 2-Aza-1,4-dienes in the Triplet Excited State and via Radical-Cation Intermediates. 2-Aza-di-π-methane Rearrangements Yielding Cyclopropylimines and<i> N</i>-Vinylaziridines
  作者：Diego Armesto、Olga Caballero、Maria J. Ortiz、Antonia R. Agarrabeitia、Mar Martin-Fontecha、M. Rosario Torres

  DOI：10.1021/jo034452g

  日期：2003.8.1

  2-aza-1,4-dienes, by using 9,10-dicyanoanthracene (DCA) as an electron-acceptor sensitizer and biphenyl as cosensitizer, brings about regioselective formation of N-vinylaziridines. Under these conditions, azadiene 1 also affords cyclopropylimine 37, resulting from an aryl-di-pi-methane rearrangement. This result demonstrates that di-pi-methane reactions can also take place via radical-cation intermediates

  通过2-氮杂-di-pi-甲烷（2-ADPM）重排途径，对2-氮杂-1,4-二烯进行三重态敏化辐照可提供N-环丙基亚胺。在五苯基取代的氮杂二烯1的情况下，辐射导致形成环丙基亚胺2以及N-乙烯基氮丙啶3。该转变代表产生三元杂环产物的二-pi-甲烷重排反应的第一个实例。通过使用9,10-二氰基蒽（DCA）作为电子受体敏化剂和联苯作为共敏化剂，对2-氮杂-1,4-二烯进行SET敏化辐照，可形成N-乙烯基氮丙啶的区域选择性形成。在这些条件下，氮杂二烯1还提供了由芳基-二-pi-甲烷重排产生的环丙基亚胺37。该结果表明，二-pi-甲烷反应也可以通过自由基阳离子中间体发生。
• A Study of the Competition between the Di-.pi.-methane and the Azadi-.pi.-methane Processes in 2-Vinyl-.beta.,.gamma.-unsaturated Oxime Derivatives. The Novel Azadi-.pi.-methane Reactivity of .beta.,.gamma.-Unsaturated Oximes
  作者：Diego Armesto、Maria J. Ortiz、Ana Ramos、William M. Horspool、Elena P. Mayoral

  DOI：10.1021/jo00105a031

  日期：1994.12

  A study aimed at detecting intramolecular competition between the di-pi-methane (DPM) rear-rangement and the azadi-pi-methane (ADPM) process has been carried out. The results show that direct or acetophenone-sensitized irradiation of 2-(2,2-diphenylvinyl)-2-methyl-4,4-diphenyl-3- butenal oxime acetate 3 and the corresponding oxime trifluoroacetate 11 undergo only the DPM process to yield cyclopropanes. Similar DPM rearrangement was observed for 2-methyl-4,4-diphenyl-2-vinyl-3-butenonitrile 22. These are examples of triplet DPM reactivity in acyclic substrates where the central carbon has only one electron-withdrawing group. There is only one case of such reactivity in the aryl di-pi-methane process. However, 2-methyl-4,4-diphenyl-2-vinyl-2-vinyl-3-butenal oxime acetate 26 and the corresponding trifluoroacetate 15 undergo the ADPM rearrangement exclusively on direct or acetophenone-sensitized irradiation. The selectivity observed is interpreted as being dependent on the relative stabilities of the 1,4-bridged biradical intermediates. Based on previous failures to observe the ADPM reactions of beta,gamma-unsaturated oximes, an attempt to suppress the ADPM reactivity in compounds with a substitution pattern such as that present in 15 and 26 was made using the parent oxime 21. Surprisingly this compound reacts efficiently by the ADPM process and affords cyclopropane 30. This is the first example of ADPM reactivity of an acyclic beta,gamma-unsaturated oxime. Ah the rearrangements described are stereoselective. This reaction was extended to other oximes 45, 47a and 47b and also to the oxime ether 36. The photoreaction of 47b shows that the ADPM rearrangement of oximes can be extended to ketone derivatives. Previous studies have shown that such reactivity is uncommon. beta,gamma-Unsaturated oximes are usually considered to be photochemically inert but these results have shown that changes in substitution can promote efficient ADPM reactivity.
• Ishibashi, Hiroyuki; Okada, Motofumi; Komatsu, Hajime, Synthesis, 1985, # 6/7, p. 643 - 645
  作者：Ishibashi, Hiroyuki、Okada, Motofumi、Komatsu, Hajime、Ikeda, Masazumi、Tamura, Yasumitsu

  DOI：——

  日期：——
• ISHIBASHI, HIROYUKI;OKADA, MOTOFUMI;KOMATSU, HAJIME;IKEDA, MASAZUMI;TAMUR+, SYNTHESIS, BRD, 1985, N 6-7, 643-645
  作者：ISHIBASHI, HIROYUKI、OKADA, MOTOFUMI、KOMATSU, HAJIME、IKEDA, MASAZUMI、TAMUR+

  DOI：——

  日期：——