2,4,7-Tris-triisopropylsilanyloxy-phenanthro[3,4-c]phenanthrene-9,12,13,16-tetraone | 321961-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2,4,7-Tris-triisopropylsilanyloxy-phenanthro[3,4-c]phenanthrene-9,12,13,16-tetraone
• 英文别名: 6,8,11-tris[tri(propan-2-yl)silyloxy]hexahelicene-1,4,13,16-tetrone
• CAS: 321961-77-7
• 化学式: C₅₃H₇₂O₇Si₃
• 分子量: 905.407
• InChiKey: LDGHREMTORNQPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.43
• 重原子数：
  63
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S)-(-)-莰烷酰氯 、 2,4,7-Tris-triisopropylsilanyloxy-phenanthro[3,4-c]phenanthrene-9,12,13,16-tetraone 在 4-二甲氨基吡啶 、 三乙胺 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以1.77 g的产率得到[1,13,16-tris[[(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl]oxy]-6,9,11-tris[tri(propan-2-yl)silyloxy]hexahelicen-4-yl] (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
  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：

  4-tosyloxy-2,7-diiodonaphthalene 在 氢氧化钾 、 正丁基锂 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 164.0h， 生成 2,4,7-Tris-triisopropylsilanyloxy-phenanthro[3,4-c]phenanthrene-9,12,13,16-tetraone
  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

• 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.