4,5-ditosyloxynaphthalene-2,7-disulfonyl chloride | 321922-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,5-ditosyloxynaphthalene-2,7-disulfonyl chloride
• 英文别名: [3,6-Bis(chlorosulfonyl)-8-(4-methylphenyl)sulfonyloxynaphthalen-1-yl] 4-methylbenzenesulfonate
• CAS: 321922-71-8
• 化学式: C₂₄H₁₈Cl₂O₁₀S₄
• 分子量: 665.571
• InChiKey: DRYWEMKUVSCVCC-UHFFFAOYSA-N

物化性质

• 熔点：
  219-221 °C
• 沸点：
  842.0±65.0 °C(Predicted)
• 密度：
  1.597±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  189
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4,5-ditosyloxynaphthalene-2,7-disulfonyl chloride 在 二(氰基苯)二氯化钯 titanium(IV) isopropylate 、 lithium chloride 、 zinc(II) iodide 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 14.0h， 以52%的产率得到4,5-ditosyloxy-2,7-diiodonaphthalene
  参考文献：
  名称：

  Expeditious Procedure To Synthesize Ethers and Esters of Tri- and Tetrahydroxy[6]helicenebisquinones from the Dye-Intermediates Disodium 4-Hydroxy- and 4,5-Dihydroxynaphthalene-2,7-disulfonates

  摘要：

  A procedure is described for synthesizing appreciable quantities of both the tetradodecyloxy[6]-helicenebisquinone 1 (R = dodecyl), which exhibits unique optical properties but previously was difficult to prepare, and a variety of analogues. The synthesis starts from disodium 4,5rlihvdroxynaphthalene-2, 7-disulfonate, the commercially available dye-interme diate known as chromotropic acid. It gives enantiopure 1, with R = (i-Pr)(3)Si, whose silyl groups can be replaced by dodecyl and hexanoyl groups. The same procedure applied to disodium 4-hydroxynaphthalene-2,7disulfonate, also an inexpensive, commercially available chemical, works equally well to produce the corresponding molecules that have one fewer side chain. Key steps are the use of tosyl groups to protect phenols and of a method described seven years ago by Satoh, Itoh, Miura, and Nomura to transform the sulfonic acid functions to iodides. The structure of tetra-(1S)-camphanate 20, the ester of the reduction product of (-)-1 [R = (i-Pr)(3)Si], was analyzed by X-ray diffraction. It shows the absolute configurations and supports the presumed basis for the rule that the (1S)-camphanates of(P)-helicen-1-ols are more polar than their (M)-diastereomers.

  DOI：

  10.1021/jo001356w
• 作为产物：
  描述：

  disodium chromotropate 在 氯化亚砜 、 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 4,5-ditosyloxynaphthalene-2,7-disulfonyl chloride
  参考文献：
  名称：

  Expeditious Procedure To Synthesize Ethers and Esters of Tri- and Tetrahydroxy[6]helicenebisquinones from the Dye-Intermediates Disodium 4-Hydroxy- and 4,5-Dihydroxynaphthalene-2,7-disulfonates

  摘要：

  A procedure is described for synthesizing appreciable quantities of both the tetradodecyloxy[6]-helicenebisquinone 1 (R = dodecyl), which exhibits unique optical properties but previously was difficult to prepare, and a variety of analogues. The synthesis starts from disodium 4,5rlihvdroxynaphthalene-2, 7-disulfonate, the commercially available dye-interme diate known as chromotropic acid. It gives enantiopure 1, with R = (i-Pr)(3)Si, whose silyl groups can be replaced by dodecyl and hexanoyl groups. The same procedure applied to disodium 4-hydroxynaphthalene-2,7disulfonate, also an inexpensive, commercially available chemical, works equally well to produce the corresponding molecules that have one fewer side chain. Key steps are the use of tosyl groups to protect phenols and of a method described seven years ago by Satoh, Itoh, Miura, and Nomura to transform the sulfonic acid functions to iodides. The structure of tetra-(1S)-camphanate 20, the ester of the reduction product of (-)-1 [R = (i-Pr)(3)Si], was analyzed by X-ray diffraction. It shows the absolute configurations and supports the presumed basis for the rule that the (1S)-camphanates of(P)-helicen-1-ols are more polar than their (M)-diastereomers.

  DOI：

  10.1021/jo001356w

文献信息

• Synthesis of macrocyclic chromotropic acid-based sulfonamides; their complexation properties and an unexpected photochemical reaction
  作者：Hisham Fathy Sleem、Louise Nicole Dawe、Paris Elias Georghiou

  DOI：10.1016/j.tetlet.2013.04.081

  日期：2013.6

  Chromotropic acid (CTA), a dihydroxynaphthalenedisulfonic acid is a reagent that is widely used for dyestuff manufacture, as a chromogen-forming reagent for the analysis of formaldehyde and as an intermediate for azo derivatives used as analytical reagents. The synthesis of two new CTA-based macrocyclic tetra-sulfonamides 7 and 7a and their corresponding bis-sulfonamides 10 and 10a and their complexation

  变色酸（CTA），一种二羟基萘二磺酸，是一种广泛用于染料生产的试剂，是用于分析甲醛的生色剂，并且是用作分析试剂的偶氮衍生物的中间体。研究了两种新的基于CTA的大环四磺酰胺7和7a及其相应的双磺酰胺10和10a的合成及其对卤化四正丁基铵的络合性能。确定了10a的X射线结构，并为四磺酰胺发生意外的光化学反应提供了关键证据。
• Expeditious Procedure To Synthesize Ethers and Esters of Tri- and Tetrahydroxy[6]helicenebisquinones from the Dye-Intermediates Disodium 4-Hydroxy- and 4,5-Dihydroxynaphthalene-2,7-disulfonates
  作者：Kamil Paruch、Libor Vyklický、Thomas J. Katz、Christopher D. Incarvito、Arnold L. Rheingold

  DOI：10.1021/jo001356w

  日期：2000.12.1

  A procedure is described for synthesizing appreciable quantities of both the tetradodecyloxy[6]-helicenebisquinone 1 (R = dodecyl), which exhibits unique optical properties but previously was difficult to prepare, and a variety of analogues. The synthesis starts from disodium 4,5rlihvdroxynaphthalene-2, 7-disulfonate, the commercially available dye-interme diate known as chromotropic acid. It gives enantiopure 1, with R = (i-Pr)(3)Si, whose silyl groups can be replaced by dodecyl and hexanoyl groups. The same procedure applied to disodium 4-hydroxynaphthalene-2,7disulfonate, also an inexpensive, commercially available chemical, works equally well to produce the corresponding molecules that have one fewer side chain. Key steps are the use of tosyl groups to protect phenols and of a method described seven years ago by Satoh, Itoh, Miura, and Nomura to transform the sulfonic acid functions to iodides. The structure of tetra-(1S)-camphanate 20, the ester of the reduction product of (-)-1 [R = (i-Pr)(3)Si], was analyzed by X-ray diffraction. It shows the absolute configurations and supports the presumed basis for the rule that the (1S)-camphanates of(P)-helicen-1-ols are more polar than their (M)-diastereomers.