2-Benzenesulfonyl-3-chloro-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalene | 612096-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-Benzenesulfonyl-3-chloro-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalene
• 英文别名: 2-(Benzenesulfonyl)-3-chloro-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene
• CAS: 612096-61-4
• 化学式: C₁₈H₁₉ClO₄S
• 分子量: 366.865
• InChiKey: SSGUXUHIMLAYCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Benzenesulfonyl-3-chloro-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalene 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到2-Benzenesulfonyl-5,8-dimethoxy-1,2-dihydro-naphthalene
  参考文献：
  名称：

  对称四芳基四萘并[2,3]卟啉的合成

  摘要：

  开发了一种新的合成内消旋-四芳基四萘并[2,3]卟啉（Ar 4 TNP）的方法。通过将其中吡咯单元与八氢或二氢萘部分稠合的内-四芳基卟啉进行氧化芳构化，可获得具有外围官能团的Ar 4 TNP 。这些前体卟啉由容易获得的起始原料（例如萘或1,4-苯醌）以四到五个步骤合成。发现源自二氢萘的途径（即“二氢萘”途径）优于替代的“八氢萘”途径，因为它（1）能够缩短总体反应顺序，（2）在范围上具有更广泛的范围Ar 4中的外围取代反应TNPs和（3）提供了更高的目标卟啉收率。合成的Ar 4 TNP的Pd配合物在710-720 nm（ε〜200 000 M - 1 cm - 1）处显示出很强的吸收带，并在室温下以适度的量子产率磷化（φ= 2-3％，λmax = 900-1000 nm）。发现与未取代的Ar 4的相应最大值相比，被八个甲氧基（Ar 4 TNP（OMe）8）取代的萘卟啉的吸收最大值约为15-20

  DOI：

  10.1021/jo047741t
• 作为产物：
  描述：

  5,8-二甲氧基-1,4-二氢萘 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-Benzenesulfonyl-3-chloro-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalene
  参考文献：
  名称：

  Synthesis and Luminescence of Soluble meso-Unsubstituted Tetrabenzo- and Tetranaphtho[2,3]porphyrins

  摘要：

  Syntheses of soluble tetrabenzoporphyrins (TBP) and tetranaphtho[2,3]porphyrins (TNP), with multiple substituents in the conjugated aromatic rings but bearing no substituents in the mesopositions, is reported. Both types of porphyrins were obtained by direct aromatization of precursor porphyrins, annealed with either cyclohexene or dihydronaphthalene fragments. TBPs and TNPs possess powerful absorption bands in the near-infrared (lambda = 610-710 nm, is an element of = 100,000-300,000 M-1 cm(-1)) and exhibit strong luminescence. Free bases and Zn complexes fluoresce with quantum yields of up to 50%, whereas Pd and Pt complexes phosphoresce in solutions at ambient temperatures. Remarkably, the phosphorescence quantum yields of Pd and Pt TBPs reach as high as 20-50%, which places them among the brightest near-infrared phosphors known to date.

  DOI：

  10.1021/jo051580r

文献信息

• Synthesis of Symmetrical Tetraaryltetranaphtho[2,3]porphyrins
  作者：Olga S. Finikova、Sergei E. Aleshchenkov、Raymond P. Briñas、Andrei V. Cheprakov、Patrick J. Carroll、Sergei A. Vinogradov

  DOI：10.1021/jo047741t

  日期：2005.6.1

  naphthalene or 1,4-benzoquinone. The pathway originating in dihydronaphthalene, i.e., the “dialine” route, was found to be superior to the alternative “octaline” route in that it (1) enables the shortening of the overall reaction sequence, (2) has a broader scope in terms of the peripheral substitution in Ar4TNPs, and (3) affords higher yields of the target porphyrins. Pd complexes of the synthesized Ar4TNPs

  开发了一种新的合成内消旋-四芳基四萘并[2,3]卟啉（Ar 4 TNP）的方法。通过将其中吡咯单元与八氢或二氢萘部分稠合的内-四芳基卟啉进行氧化芳构化，可获得具有外围官能团的Ar 4 TNP 。这些前体卟啉由容易获得的起始原料（例如萘或1,4-苯醌）以四到五个步骤合成。发现源自二氢萘的途径（即“二氢萘”途径）优于替代的“八氢萘”途径，因为它（1）能够缩短总体反应顺序，（2）在范围上具有更广泛的范围Ar 4中的外围取代反应TNPs和（3）提供了更高的目标卟啉收率。合成的Ar 4 TNP的Pd配合物在710-720 nm（ε〜200 000 M - 1 cm - 1）处显示出很强的吸收带，并在室温下以适度的量子产率磷化（φ= 2-3％，λmax = 900-1000 nm）。发现与未取代的Ar 4的相应最大值相比，被八个甲氧基（Ar 4 TNP（OMe）8）取代的萘卟啉的吸收最大值约为15-20
• Synthesis and Luminescence of Soluble <i>m</i><i>eso-</i>Unsubstituted Tetrabenzo- and Tetranaphtho[2,3]porphyrins
  作者：Olga S. Finikova、Andrei V. Cheprakov、Sergei A. Vinogradov

  DOI：10.1021/jo051580r

  日期：2005.11.1

  Syntheses of soluble tetrabenzoporphyrins (TBP) and tetranaphtho[2,3]porphyrins (TNP), with multiple substituents in the conjugated aromatic rings but bearing no substituents in the mesopositions, is reported. Both types of porphyrins were obtained by direct aromatization of precursor porphyrins, annealed with either cyclohexene or dihydronaphthalene fragments. TBPs and TNPs possess powerful absorption bands in the near-infrared (lambda = 610-710 nm, is an element of = 100,000-300,000 M-1 cm(-1)) and exhibit strong luminescence. Free bases and Zn complexes fluoresce with quantum yields of up to 50%, whereas Pd and Pt complexes phosphoresce in solutions at ambient temperatures. Remarkably, the phosphorescence quantum yields of Pd and Pt TBPs reach as high as 20-50%, which places them among the brightest near-infrared phosphors known to date.