Dimethyl syn-2,10-dithia<3>(1,3)cyclo<3>(2,4)pyrrolophane-6,8-dicarboxylate | 159217-29-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Dimethyl syn-2,10-dithia<3>(1,3)cyclo<3>(2,4)pyrrolophane-6,8-dicarboxylate
• 英文别名: Dimethyl 6-methyl-3,10-dithia-6-azatricyclo[10.3.1.15,8]heptadeca-1(15),5(17),7,12(16),13-pentaene-7,17-dicarboxylate
• CAS: 159217-29-5
• 化学式: C₁₉H₂₁NO₄S₂
• 分子量: 391.512
• InChiKey: CZLOOFVNSJELKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  618.7±55.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Dimethyl syn-2,10-dithia<3>(1,3)cyclo<3>(2,4)pyrrolophane-6,8-dicarboxylate 在 W-7 Raney Nickel 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 26.33h， 生成 Dimethyl anti-<2>(1,3)cyclo<23>(2,4)pyrrolophane-5,7-dicarboxylate
  参考文献：
  名称：

  Synthesis and Conformational Study of the First Dithia[3]metacyclo[3](2,4)pyrrolophane and [2]Metacyclo[2](2,4)pyrrolophane. 1H NMR Spectroscopic Evidence for a Novel Hydrogen-Bonding Phenomenon

  摘要：

  The first examples of a dithia[3]metacyclo[3](2,4)pyrrolophane and a [2]metacyclo[2](2,4)pyrrolophane, namely 3g and 4g, respectively, were synthesized. The dithiacyclophane 3g was found to adopt the syn conformation both in solid state and in solution. Results from the H-1 NMR spectroscopic study of 3g suggest a novel hydrogen-bonding between a relatively ''nonacidic'' bridging methylene proton and the carbonyl oxygen of the ''internal'' ester group at C8. X-ray crystallographic data indicate an unexpectedly small inclination angle of the two aromatic rings in 3g which would minimize the steric interaction between the syn ester group at C8 and H17. The [2(2)]cyclophane 4g was found to adopt the anti conformation both in solid state and in solution. Results from the H-1 NMR spectroscopic study of 4g show that the methoxy protons of the ''internal'' ester group at C7 are still located in the shielding zone of the opposite anti benzene ring. X-ray crystallographic data indicate an unexpectedly large inclination angle of the two aromatic rings in 4g which would minimize the steric interaction between the ester group at C7 and the opposite benzene ring.

  DOI：

  10.1021/jo00103a027
• 作为产物：
  描述：

  dimethyl 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 四丁基硫酸氢铵 作用下， 以 四氯化碳 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 20.0h， 生成 Dimethyl syn-2,10-dithia<3>(1,3)cyclo<3>(2,4)pyrrolophane-6,8-dicarboxylate
  参考文献：
  名称：

  Synthesis and Conformational Study of the First Dithia[3]metacyclo[3](2,4)pyrrolophane and [2]Metacyclo[2](2,4)pyrrolophane. 1H NMR Spectroscopic Evidence for a Novel Hydrogen-Bonding Phenomenon

  摘要：

  The first examples of a dithia[3]metacyclo[3](2,4)pyrrolophane and a [2]metacyclo[2](2,4)pyrrolophane, namely 3g and 4g, respectively, were synthesized. The dithiacyclophane 3g was found to adopt the syn conformation both in solid state and in solution. Results from the H-1 NMR spectroscopic study of 3g suggest a novel hydrogen-bonding between a relatively ''nonacidic'' bridging methylene proton and the carbonyl oxygen of the ''internal'' ester group at C8. X-ray crystallographic data indicate an unexpectedly small inclination angle of the two aromatic rings in 3g which would minimize the steric interaction between the syn ester group at C8 and H17. The [2(2)]cyclophane 4g was found to adopt the anti conformation both in solid state and in solution. Results from the H-1 NMR spectroscopic study of 4g show that the methoxy protons of the ''internal'' ester group at C7 are still located in the shielding zone of the opposite anti benzene ring. X-ray crystallographic data indicate an unexpectedly large inclination angle of the two aromatic rings in 4g which would minimize the steric interaction between the ester group at C7 and the opposite benzene ring.

  DOI：

  10.1021/jo00103a027

文献信息

• Synthesis and Conformational Study of the First Dithia[3]metacyclo[3](2,4)pyrrolophane and [2]Metacyclo[2](2,4)pyrrolophane. 1H NMR Spectroscopic Evidence for a Novel Hydrogen-Bonding Phenomenon
  作者：Yee-Hing Lai、K. F. Mok、Yuhua Ting

  DOI：10.1021/jo00103a027

  日期：1994.12

  The first examples of a dithia[3]metacyclo[3](2,4)pyrrolophane and a [2]metacyclo[2](2,4)pyrrolophane, namely 3g and 4g, respectively, were synthesized. The dithiacyclophane 3g was found to adopt the syn conformation both in solid state and in solution. Results from the H-1 NMR spectroscopic study of 3g suggest a novel hydrogen-bonding between a relatively ''nonacidic'' bridging methylene proton and the carbonyl oxygen of the ''internal'' ester group at C8. X-ray crystallographic data indicate an unexpectedly small inclination angle of the two aromatic rings in 3g which would minimize the steric interaction between the syn ester group at C8 and H17. The [2(2)]cyclophane 4g was found to adopt the anti conformation both in solid state and in solution. Results from the H-1 NMR spectroscopic study of 4g show that the methoxy protons of the ''internal'' ester group at C7 are still located in the shielding zone of the opposite anti benzene ring. X-ray crystallographic data indicate an unexpectedly large inclination angle of the two aromatic rings in 4g which would minimize the steric interaction between the ester group at C7 and the opposite benzene ring.