naphthalene-2,3-dicarboxylic acid diethyl ester | 50919-54-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalene-2,3-dicarboxylic acid diethyl ester
• 英文别名: diethyl naphthalene-2,3-dicarboxylate；diethyl 2,3-naphthalenedicarboxylate；diethyl-2,3-naphthalenedicarboxylate；2,3-bis(ethoxycarbonyl)-naphthalene；2,3-diethoxycarbonylnaphthalene；Naphthalin-2,3-dicarbonsaeure-diaethylester
• CAS: 50919-54-5
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: YEHPWDJFRGQQIM-UHFFFAOYSA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  374.0±15.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  naphthalene-2,3-dicarboxylic acid diethyl ester 在 sodium hydride 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 以91%的产率得到1H-cyclopenta[b]naphthalene-1,3(2H)-dione
  参考文献：
  名称：

  基于2-（3-氧代-2,3-二氢-1 H-环戊[ b ]萘-1-亚烷基）丙二腈的新型推挽染料：一种胺定向合成

  摘要：

  使用2-（3-氧代-2,3-二氢-1 H-环戊[ b ]萘-1-亚烷基）丙二腈作为电子受体设计了一系列十二种染料。当使用哌啶作为Knoevenagel反应的经典碱时，发生了胺对形成的推挽生色团的亲核攻击，产生了氮杂芴酮衍生物。通过改变胺，可以获得一系列的氮杂芴酮。通过使用扩展共轭的醛，还可以证明环化反应后的自发芳构化。检查了不同染料的光学，电化学性质。还进行了理论计算以支持实验结果。

  DOI：

  10.1016/j.dyepig.2020.108182
• 作为产物：
  描述：

  3-(2-(ethoxycarbonylethynyl)phenyl)prop-2-ynoic acid ethyl ester 在 1,4-环己二烯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以90%的产率得到naphthalene-2,3-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Carbonyl- and Carboxyl-Substituted Enediynes:  Synthesis, Computations, and Thermal Reactivity

  摘要：

  The influence of electron-withdrawing groups (carbonyl and carboxyl) at the alkyne termini on the reactivity of enediynes was investigated by a combination of experimental and computational techniques. While the general chemical reactivity of such enediynes, especially if non-benzannelated, is increased markedly, the thermal cyclization, giving rise to Bergman cyclization products, is changed little relative to the parent enediyne system. This is evident from kinetic measurements and from density functional theory (DFT, BLYP/6-31G* + thermal corrections) computations of the experimental systems which show that the Bergman cyclization barriers slightly (3-4 kcal/mol) increase, in contrast to earlier theoretical predictions. The effect on the endothermicities is large (Delta DeltaH(r) = 7-12 kcal/mol). Hence, the increased reactivity of the substituted enediynes is entirely due to nucleophiles or radicals present in solution. This was demonstrated by quantitative experiments with diethylamine and tetramethyl piperidyl oxide (TEMPO) which both give fulvenes through 5-exo-dig cyclizations.

  DOI：

  10.1021/jo001417q

文献信息

• Synthesis of phthalic acid derivatives <i>via</i> Pd-catalyzed alkoxycarbonylation of aromatic C–H bonds with alkyl chloroformates
  作者：Gang Liao、Hao-Ming Chen、Bing-Feng Shi

  DOI：10.1039/c8cc06663a

  日期：——

  A Pd(II)-catalyzed alkoxycarbonylation of aromatic C–H bonds with alkyl chloroformates has been developed. A broad range of benzamides and alkyl chloroformates are compatible with this protocol. The reaction is operationally simple and scalable. The direct group could be readily removed to access substituted phthalic acid esters (PAEs), 1,2-dibenzyl alcohols and phthalamides. Besides alkoxycarbonylation

  已经开发了钯（II）催化的带有烷基氯甲酸酯的芳香族碳氢键的烷氧基羰基化反应。各种各样的苯甲酰胺和烷基氯甲酸酯都与此协议兼容。该反应操作简单且可扩展。可以容易地除去直接基团以得到取代的邻苯二甲酸酯（PAE），1，2-二苄基醇和邻苯二甲酰胺。除了苯甲酰胺β-CH键的烷氧羰基化以外，2-苯基乙酰胺的γ-烷氧羰基化也是可行的。
• Nondirected C-H Alkenylation of Arenes with Alkenes under Rhodium Catalysis
  作者：Koushik Ghosh、Gen Mihara、Yuji Nishii、Masahiro Miura

  DOI：10.1246/cl.180907

  日期：2019.2.5

  A nondirected dehydrogenative direct alkenylation of simple aromatic compounds with alkenes under rhodium catalysis is described. The site-selectivity is dominantly dictated by the steric bulkiness...

  描述了在铑催化下，简单芳香族化合物与烯烃的非定向脱氢直接烯基化。位点选择性主要取决于空间体积...
• Facile Sc(OTf)₃-Catalyzed Generation and Successive Aromatization of Isobenzofuran from <i>o</i>-Dicarbonylbenzenes
  作者：Yuta Nishina、Tatsuya Kida、Tomonari Ureshino

  DOI：10.1021/ol201479p

  日期：2011.8.5

  Isobenzofuran can be prepared from o-phthalaldehyde using hydrosilane. The formed isobenzofuran is trapped by an alkene via a Diels–Alder reaction. Further dehydration proceeds to furnish the conjugated aromatic compound. This multistep reaction was promoted by catalytic amounts of Sc(OTf)3.

  异苯并呋喃可以使用氢化硅烷由邻苯二甲醛制备。形成的异苯并呋喃通过狄尔斯-阿尔德反应被烯烃捕获。进一步脱水以提供共轭芳族化合物。催化量的Sc（OTf）3促进了该多步反应。
• Iterative synthesis of acenesvia homo-elongation
  作者：Chih-Hsiu Lin、Ke-Han Lin、Bikash Pal、Li-Der Tsou

  DOI：10.1039/b814840f

  日期：——

  Starting from aromaticortho-dialdehydes, we devised a homo-elongation protocol that combines a Wittig olefination and subsequent intramolecular Knoevenagel condensation to produce acene diesters and dinitriles.

  从芳香邻二醛出发，我们设计了一套同系延长方案，结合了Wittig烯化反应和随后的分子内Knoevenagel缩合反应，以生成并五烷二酯和二腈。
• Functionalized esters as bis-electrophiles in a silicon-induced domino synthesis of annulated carbocycles
  作者：Florian Genrich、Guido Harms、Ernst Schaumann、Mimoza Gjikaj、Gunadi Adiwidjaja

  DOI：10.1016/j.tet.2009.01.119

  日期：2009.7

  The reaction of silyl-substituted carbanion 1b with arene-1,2-dicarboxylates 6, 15 yields indenone derivatives 11, 16 in a domino process involving silyl C→O migration and elimination. However, in a competing pathway, the initial addition of 1b leads to lactone formation (8, 17). Substrates 26, 38 containing an ester group and a bromine substituent react with 1b under substitution of the halogen not

  甲硅烷基取代的碳负离子反应1B与芳烃- 1,2-二羧酸酯6，15个产量茚酮衍生物11，16在涉及甲硅烷→O;迁移和消除℃的多米诺过程。然而，在竞争途径中，初始加入1B导致内酯的形成（8，17）。基底26，38含酯基团和取代基溴与反应1b的下不允许甲硅烷迁移卤素取代。但是用TBAF进行的去甲硅烷基化反应会产生反应性碳负离子，从而提供苯并环化的环烷酮29，40。