[(2R)-1-methoxy-1-oxopropan-2-yl] naphthalene-2-carboxylate | 1186490-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(2R)-1-methoxy-1-oxopropan-2-yl] naphthalene-2-carboxylate
• CAS: 1186490-89-0
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: KSELHOLMSHHCKP-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：

  [(2R)-1-methoxy-1-oxopropan-2-yl] 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：

  D-(+)-乳酸甲酯 、 2-萘甲酰氯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 [(2R)-1-methoxy-1-oxopropan-2-yl] naphthalene-2-carboxylate
  参考文献：
  名称：

  与手性助剂的非对映异构化2-萘甲酸烷基酯的光二聚化

  摘要：

  2-萘甲酸烷基酯与手性助剂的光二聚化产生了类似古巴的抗头对头光二聚体，收率达93％，非对映体过量高达59％。在除去手性助剂后，以80％的产率获得了2-萘甲酸的类似古巴的光二聚体的手性对映体。

  DOI：

  10.1016/j.tetlet.2009.06.053

文献信息

• Diastereodifferentiating photodimerization of alkyl 2-naphthoates with chiral auxiliaries
  作者：Hong-Xia Xu、Bin Chen、Li-Ping Zhang、Li-Zhu Wu、Chen-Ho Tung

  DOI：10.1016/j.tetlet.2009.06.053

  日期：2009.9

  Photodimerization of alkyl 2-naphthoates with chiral auxiliaries resulted in cubane-like anti head-to-head photodimers in 93% yield and with up to 59% diastereomeric excess. After removal of the chiral auxiliaries enantiomers of cubane-like photodimer of 2-naphthalene carboxylic acid were obtained in 80% yield.

  2-萘甲酸烷基酯与手性助剂的光二聚化产生了类似古巴的抗头对头光二聚体，收率达93％，非对映体过量高达59％。在除去手性助剂后，以80％的产率获得了2-萘甲酸的类似古巴的光二聚体的手性对映体。
• 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.