ethyl 3-[[2-(4-methoxymethylphenyl)]-1,3-dithiolan-2-yl]propiolate | 1234041-66-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3-[[2-(4-methoxymethylphenyl)]-1,3-dithiolan-2-yl]propiolate
• 英文别名: Ethyl 3-[2-[4-(methoxymethyl)phenyl]-1,3-dithiolan-2-yl]prop-2-ynoate
• CAS: 1234041-66-7
• 化学式: C₁₆H₁₈O₃S₂
• 分子量: 322.449
• InChiKey: BNBFJXVMPDSCNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  86.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-[[2-(4-methoxymethylphenyl)]-1,3-dithiolan-2-yl]propiolate 、 phenanthrene-3,6-dicarbaldehyde 在 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.83h， 以40%的产率得到Ethyl 2-[6-[3-ethoxycarbonyl-5-[4-(methoxymethyl)phenyl]furan-2-yl]phenanthren-3-yl]-5-[4-(methoxymethyl)phenyl]furan-3-carboxylate
  参考文献：
  名称：

  Phenanthrene-Tethered Furan-Containing Cyclophenes: Synthesis and Photophysical Properties

  摘要：

  Two phenanthrene-fused furan-containing teraryl cyclophenes 5 and 6 are synthesized. These cyclophenes exhibit charge transfer band in the absorption spectra, unusually large Stokes shifts in the emission spectra, and exceptionally high mu beta values in the electric-field-induced second-harmonic generation (EFISH) experiments. The mu beta(1.91) values for 5 and 6 are 438 and 777 x 10(-48) esu, respectively. The bridging double bond in 5 and 6 can serve as either an electron donor or acceptor depending on the nature of the substituent on furan rings. DFT calculations at the B3LYP/6-31G** level indicate that the electron density distributions in HOMO and LUMO are very different. Interaction between the oligoaryl systems and the double bond may account for the significant enhancement in hyperpolarizability.

  DOI：

  10.1021/jo100873z
• 作为产物：
  描述：

  2-ethynyl-2-(4-methoxymethylphenyl)-1,3-dithiolane 、 氯甲酸乙酯 在 甲基碘化镁 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以94%的产率得到ethyl 3-[[2-(4-methoxymethylphenyl)]-1,3-dithiolan-2-yl]propiolate
  参考文献：
  名称：

  Phenanthrene-Tethered Furan-Containing Cyclophenes: Synthesis and Photophysical Properties

  摘要：

  Two phenanthrene-fused furan-containing teraryl cyclophenes 5 and 6 are synthesized. These cyclophenes exhibit charge transfer band in the absorption spectra, unusually large Stokes shifts in the emission spectra, and exceptionally high mu beta values in the electric-field-induced second-harmonic generation (EFISH) experiments. The mu beta(1.91) values for 5 and 6 are 438 and 777 x 10(-48) esu, respectively. The bridging double bond in 5 and 6 can serve as either an electron donor or acceptor depending on the nature of the substituent on furan rings. DFT calculations at the B3LYP/6-31G** level indicate that the electron density distributions in HOMO and LUMO are very different. Interaction between the oligoaryl systems and the double bond may account for the significant enhancement in hyperpolarizability.

  DOI：

  10.1021/jo100873z

文献信息

• Phenanthrene-Tethered Furan-Containing Cyclophenes: Synthesis and Photophysical Properties
  作者：Hao-Tien Bai、Hsin-Chieh Lin、Tien-Yau Luh

  DOI：10.1021/jo100873z

  日期：2010.7.2

  Two phenanthrene-fused furan-containing teraryl cyclophenes 5 and 6 are synthesized. These cyclophenes exhibit charge transfer band in the absorption spectra, unusually large Stokes shifts in the emission spectra, and exceptionally high mu beta values in the electric-field-induced second-harmonic generation (EFISH) experiments. The mu beta(1.91) values for 5 and 6 are 438 and 777 x 10(-48) esu, respectively. The bridging double bond in 5 and 6 can serve as either an electron donor or acceptor depending on the nature of the substituent on furan rings. DFT calculations at the B3LYP/6-31G** level indicate that the electron density distributions in HOMO and LUMO are very different. Interaction between the oligoaryl systems and the double bond may account for the significant enhancement in hyperpolarizability.