(2-Methoxy-2-oxoethyl) naphthalene-2-carboxylate | 1357175-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2-Methoxy-2-oxoethyl) naphthalene-2-carboxylate
• 英文别名: (2-methoxy-2-oxoethyl) naphthalene-2-carboxylate
• CAS: 1357175-22-4
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: JPABHIIVHGDHBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  (2-Methoxy-2-oxoethyl) naphthalene-2-carboxylate 、 γ-环糊精 以 二氯甲烷 、 水 为溶剂， 生成
  参考文献：
  名称：

  Enhancement of Diastereoselectivity in Photodimerization of Alkyl 2-Naphthoates with Chiral Auxiliaries via Inclusion within γ-Cyclodextrin Cavities

  摘要：

  Irradiations of alkyl 2-naphthoates are known to result in four isomeric "cubane-like" photodimers: anti(HH)-2, syn(HH)-2, anti(HT)-2, and syn(HT)-2 where the anti(HH)-2, anti(HT)-2, and syn(HT)-2 consist of pairs of diastereomers. Here, chiral auxiliary and chiral microreactor strategies have been combined to achieve high diastereoselectivity in photo-dimerizations of an enantiomeric pair of 2-naphthoates with (R)- and (S)-1-methoxycarbonylethyl esters as chiral auxiliaries (1R and 1S). Thus, irradiations of their gamma-cyclodextrin (gamma-CD) complexes have been conducted. Fluorescence, IR, and NMR spectra of both enantiomers of I demonstrate that their gamma-CD complexes are mainly 2:2 with the molecules of 1 in head-to-head orientations. Irradiation of the complexes in the solid state mainly resulted in anti(HH)-2. The absolute configuration of each diastereomer of anti(HH)-2 has been established for the first time here. The diastereomeric excesses (de's) of anti(HH)-2 from IR and 15 were 94% and 86%, respectively. These de's are much higher than those found from irradiations in solution (55% for IR and 1S), where the opposite diastereomeric form is in excess! Calculations of the energies of various conformations of the head-to-head 2:2 inclusion complexes were performed using the PM3 approach. The predicted major diastereomers based on the calculation are consistent with those found experimentally.

  DOI：

  10.1021/jo2020328
• 作为产物：
  描述：

  丙二酸二甲酯 、 2-萘甲酸 在 叔丁基过氧化氢 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以70%的产率得到(2-Methoxy-2-oxoethyl) naphthalene-2-carboxylate
  参考文献：
  名称：

  Temperature-controlled NaI-mediated α-oxybenzoylation or oxyacylation–decarboxylation reactions of dimethyl malonate with carboxylic acids

  摘要：

  A NaI-mediated alpha-functionalization of dimethyl malonate and its derivatives with carboxylic acids has been developed. Two different reaction routes based on the same substrates and reaction conditions by simply altering the reaction temperature have been observed, which led to the synthesis of two types of products in good to high yields. The scope of substrates was investigated for both types of reactions, respectively, and possible reaction mechanisms were suggested. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2015.07.013

文献信息

• Temperature-controlled NaI-mediated α-oxybenzoylation or oxyacylation–decarboxylation reactions of dimethyl malonate with carboxylic acids
  作者：Jincheng Mao、Defu Liu、Yongming Li、Jinzhou Zhao、Guangwei Rong、Hong Yan、Guoqi Zhang

  DOI：10.1016/j.catcom.2015.07.013

  日期：2015.10

  A NaI-mediated alpha-functionalization of dimethyl malonate and its derivatives with carboxylic acids has been developed. Two different reaction routes based on the same substrates and reaction conditions by simply altering the reaction temperature have been observed, which led to the synthesis of two types of products in good to high yields. The scope of substrates was investigated for both types of reactions, respectively, and possible reaction mechanisms were suggested. (C) 2015 Elsevier B.V. All rights reserved.
• Enhancement of Diastereoselectivity in Photodimerization of Alkyl 2-Naphthoates with Chiral Auxiliaries via Inclusion within γ-Cyclodextrin Cavities
  作者：Hong-Xia Xu、Su-Fang Cheng、Xiu-Jie Yang、Bin Chen、Yue Chen、Li-Ping Zhang、Li-Zhu Wu、Weihai Fang、Chen-Ho Tung、Richard G. Weiss

  DOI：10.1021/jo2020328

  日期：2012.2.17

  Irradiations of alkyl 2-naphthoates are known to result in four isomeric "cubane-like" photodimers: anti(HH)-2, syn(HH)-2, anti(HT)-2, and syn(HT)-2 where the anti(HH)-2, anti(HT)-2, and syn(HT)-2 consist of pairs of diastereomers. Here, chiral auxiliary and chiral microreactor strategies have been combined to achieve high diastereoselectivity in photo-dimerizations of an enantiomeric pair of 2-naphthoates with (R)- and (S)-1-methoxycarbonylethyl esters as chiral auxiliaries (1R and 1S). Thus, irradiations of their gamma-cyclodextrin (gamma-CD) complexes have been conducted. Fluorescence, IR, and NMR spectra of both enantiomers of I demonstrate that their gamma-CD complexes are mainly 2:2 with the molecules of 1 in head-to-head orientations. Irradiation of the complexes in the solid state mainly resulted in anti(HH)-2. The absolute configuration of each diastereomer of anti(HH)-2 has been established for the first time here. The diastereomeric excesses (de's) of anti(HH)-2 from IR and 15 were 94% and 86%, respectively. These de's are much higher than those found from irradiations in solution (55% for IR and 1S), where the opposite diastereomeric form is in excess! Calculations of the energies of various conformations of the head-to-head 2:2 inclusion complexes were performed using the PM3 approach. The predicted major diastereomers based on the calculation are consistent with those found experimentally.