dimethyl 2-(naphthalen-1-yl)malonate | 82803-76-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl 2-(naphthalen-1-yl)malonate
• 英文别名: Dimethyl 2-naphthalen-1-ylpropanedioate
• CAS: 82803-76-7
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: ZGHREZLTQXESJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(naphthalen-1-yl)malonate 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 40.25h， 生成 α-methoxycarbonyl-α-(1-naphthyl)-γ-methylidene-δ-valerolactone
  参考文献：
  名称：

  钯催化的脱芳烃 [4 + 2]-环加成氢咔唑

  摘要：

  开发了一种通过高度非对映选择性钯催化的 [4 + 2]-环加成/脱芳构化 3-硝基吲哚来构建具有三个连续空间位阻立构中心（两个四元和一个三元）的氢咔唑的有效方法。3-硝基吲哚的环加成发生在环境条件下，1,4-两性离子中间体由 γ-亚甲基-δ-戊内酯原位生成。该方法的进一步综合效用通过产品可能的多方面转换得到证明。还探索了这种转化的催化不对称方面。

  DOI：

  10.1021/acs.joc.2c01869
• 作为产物：
  描述：

  萘 反应 26.25h， 生成 dimethyl 2-(naphthalen-1-yl)malonate
  参考文献：
  名称：

  萘2,3键中的碳原子加成和双（甲氧基羰基）卡宾的热Wolff重排

  摘要：

  Reaction of naphthalene with bis(methoxycarbonyl)carben(2) produced thermally from dimethyl diazomalonate (1) gives 7,7-bis(methoxycarbonyl)-2,3-benzobicyclo[4.1.0]-hepta-2,4-diene (4), dimethyl (1-naphthyl)malonate (5), dimethyl 2,3-bis(methoxycarbonyl)fumarate (6), the azine 7, 5,5,8,8-tetrakis(methoxycarbonyl)-2,3-benzotricyclo[5.1.0.0(4,6)]oct-2-ene (8), 7,7-bis(methoxycarbonyl)-3,4-benzotropilidene (9) and the two dimers, 10 and 11. Product 9 represents the first time a carbene has been observed to add to the 2,3-bond of naphthalene. The Wolff rearrangement derived products (10 and 11) demonstrate that this rearrangement can occur at temperatures as low as 120-degrees-C and this is the first time product 11 has been observed.

  DOI：

  10.1016/s0040-4039(00)74470-4

文献信息

• Diastereoselective synthesis of ω-phosphonic acid analogues of 4-arylkainoids
  作者：Yoko Yuasa、Nobuko Fujimaki、Tsutomu Yokomatsu、Jun Ando、Shiroshi Shibuya

  DOI：10.1039/a804666b

  日期：——

  Radical cyclisation by the use of α,β-unsaturated phosphonate as a radical acceptor was applied to a synthesis of 7-phosphonomethylpyrrolo[1,2-c]oxazolidinones, synthetic intermediates on the route to phosphonic acid analogues of kainoids. The relative configuration at the 6;7;7a-positions was found to be highly controlled by steric effects due to the substituent at the 6-position. Thus, diethyl [(6S*,7R*,7aS*)-6-(2-methoxyphenyl)-3-oxoperhydropyrrolo[1,2-c][1,3]oxazol-7-yl}methyl]phosphonate 29a and diethyl [(6S*,7R*,7aS*)-3-oxo-6-phenylperhydropyrrolo[1,2-c][1,3]oxazol-7-yl}methyl]phosphonate 29b were prepared with high diastereoselectivity. When the substituent at the 6-position is a 1-naphthyl group, the diethyl [(6S*,7R*,7aS*)-6-(1-naphthyl)pyrroloxazol-7-yl}methyl]phosphonate 29c and its (6S*,7R*,7aR*)-isomer 30c were formed in the ratio 29c∶30c ≈ 2∶1. The stereostructure of compound 29a was determined by X-ray crystallographic analysis. The 6-o-methoxyphenyl derivative 29a was converted into the corresponding phosphonic acid analogue 33.

  利用α,β-不饱和膦酸酯作为自由基受体的激进环化反应被应用于7-膦酰甲基吡咯并[1,2-c]噁唑啉酮的合成，这些是通往类藻肽磷酸类似物的合成中间体。发现在6;7;7a位置的相对构型受到6位取代基的立体效应的高度控制。因此，二乙基[(6S*,7R*,7aS*)-6-(2-甲氧基苯基)-3-氧代全氢吡咯并[1,2-c][1,3]噁唑啉-7-基}甲基]膦酸酯29a和二乙基[(6S*,7R*,7aS*)-3-氧代-6-苯基全氢吡咯并[1,2-c][1,3]噁唑啉-7-基}甲基]膦酸酯29b以高度的非对映选择性制备。当6位取代基为1-萘基时，二乙基[(6S*,7R*,7aS*)-6-(1-萘基)吡咯噁唑啉-7-基}甲基]膦酸酯29c及其(6S*,7R*,7aR*)异构体30c以29c:30c≈2:1的比例形成。化合物29a的立体结构通过X射线晶体学分析确定。6-邻甲氧基苯基衍生物29a被转化为相应的膦酸类似物33。
• Gold(I)‐Catalyzed Enantioselective Desymmetrization of 1,3‐Diols through Intramolecular Hydroalkoxylation of Allenes
  作者：Weiwei Zi、F. Dean Toste

  DOI：10.1002/anie.201508331

  日期：2015.11.23

  A gold(I)‐catalyzed enantioselective desymmetrization of 1,3‐diols was achieved by intramolecular hydroalkoxylation of allenes. The catalyst system 3‐F‐dppe(AuCl)2 /(R)‐C8‐TRIPAg proved to be specifically efficient to promote the desymmetrizing cyclization of 2‐aryl‐1,3‐diols, which have proven challenging substrates in previous reports. Multisubstituted tetrahydrofurans were prepared in good yield

  通过丙二烯的分子内加氢烷氧基化实现了金 (I) 催化的 1,3-二醇的对映选择性去对称化。催化剂体系 3-F-dppe(AuCl) 2  /( R )-C 8 -TRIPAg 被证明对于促进 2-芳基-1,3-二醇的去对称环化特别有效，这在之前的报告中已被证明是具有挑战性的底物。该方法以良好的收率制备了多取代四氢呋喃，具有良好的对映选择性和非对映选择性。
• Catalytic Enantioselective Synthesis of Atropisomeric Biaryls: A Cation-Directed Nucleophilic Aromatic Substitution Reaction
  作者：Roly J. Armstrong、Martin D. Smith

  DOI：10.1002/anie.201408205

  日期：2014.11.17

  enantioselective nucleophilic aromatic substitution reaction which yields axially chiral biaryl derivatives in excellent yields with e.r. values of up to 97:3 has been developed. This process uses a chiral counterion to direct the addition of thiophenolate to a prochiral dichloropyrimidine by a tandem desymmetrization/kinetic resolution mechanism. The products can be derivatized to a range of atropisomeric

  已经开发出催化对映体选择性亲核芳族取代反应，该反应以优异的收率和高达97：3的er值产生轴向手性联芳基衍生物。该方法使用手性抗衡离子通过串联不对称化/动力学拆分机制将硫酚盐添加到前手性二氯嘧啶上。该产物可以衍生为一系列的阻转异构体结构，而对映体富集度没有任何降低，因此提供了未开发的手性联芳基结构的途径。
• Dimethyl arylmalonates from cerium(IV) ammonium nitrate promoted reactions of dimethyl malonate with aromatic compounds in methanol
  作者：Enrico Baciocchi、Donatella Dell'Aira、Renzo Ruzziconi

  DOI：10.1016/s0040-4039(00)84638-9

  日期：——

  Aromatic compounds undergo homolytic malonylation by reaction with cerium(IV) ammonium nitrate and dimethyl malonate in methanol at room temperature.

  室温下，芳族化合物与硝酸铈（IV）铵和丙二酸二甲酯在甲醇中反应，进行均相丙二酰化反应。
• High-Yield Double Cyclopropanation of Benzene
  作者：M. Yang、T. R. Webb、P. Livant

  DOI：10.1021/jo010277x

  日期：2001.7.1