3,5,7,10,12,14,17,19,21,24,26,28-dodecamethyl<1.1.1.1>metacyclophane-4,18-diol | 145572-25-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,5,7,10,12,14,17,19,21,24,26,28-dodecamethyl<1.1.1.1>metacyclophane-4,18-diol
• 英文别名: 3,5,7,10,12,14,17,19,21,24,26,28-dodecamethyl[1.1.1.1]metacyclophane-4,18-diol；4,6,10,12,16,18,22,24,25,26,27,28-Dodecamethylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-5,17-diol
• CAS: 145572-25-4
• 化学式: C₄₀H₄₈O₂
• 分子量: 560.82
• InChiKey: LYYYKNYABUBEQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  42
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5,7,10,12,14,17,19,21,24,26,28-dodecamethyl<1.1.1.1>metacyclophane-4,18-diol 在 sodium hydroxide 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 4,18-bis(carboxymethyl)-3,5,7,10,12,14,17,19,21,24,26,28-dodecamethyl<1.1.1.1>metacyclophane
  参考文献：
  名称：

  Mesitylene-derived 1,3-alternate [1.1.1.1]metacyclophanes

  摘要：

  Synthetic procedures to conformationally immobile 1,3-alternate [1.1.1.1]metacyclophanes based on mesitylene units are described. Coupling of mesitol (19) with bis(chloromethyl)mesitol (20) and bis(chloromethyl)mesitylene (21) in nitroethane in the presence of SnCl4 affords metacyclophanes 6 and 7-10, respectively, possessing extra-annular hydroxyl groups. Metacyclophanes 12 and 14, which hold one or two pairs of carboxyl groups in the distal positions, have been obtained from the appropriate distal diol 8 and tetrol 6 by treatment with tert-butyl bromoacetate followed by basic hydrolysis. Functionalized molecular frameworks, such as 15 and 18, have been also prepared in high yield by direct methods. The H-1 NMR spectral characteristics of 1,3-alternate metacyclophanes synthesized are briefly discussed. The structures of mono-, tri-, and tetrahydroxy metacyclophanes 10, 7, and 6, respectively, have been determined by X-ray crystallography. All three macrocycles have very similar 1,3-alternate-biconic conformations with approximate 42mBAR symmetry. Molecules 10 and 7 are isomorphous, and the lone hydroxyl group in 10 and the three hydroxyl groups in 7 are disordered over four possible sites. A toluene of solvation is docked against the molecular cavity in both 10 and 7. Compound 6 has crystallographic 2-fold symmetry and what would have been voids in the crystal lattice are occupied by disordered solvent molecules.

  DOI：

  10.1021/jo00052a023
• 作为产物：
  描述：

  2,4,6-三甲酚 、 2,4-双(氯甲基)三甲基苯 在 四氯化锡 作用下， 以 various solvent(s) 为溶剂， 反应 13.0h， 以9%的产率得到3,5,7,10,12,14,17,19,21,24,26,28-dodecamethyl<1.1.1.1>metacyclophan-4-ol
  参考文献：
  名称：

  Mesitylene-derived 1,3-alternate [1.1.1.1]metacyclophanes

  摘要：

  Synthetic procedures to conformationally immobile 1,3-alternate [1.1.1.1]metacyclophanes based on mesitylene units are described. Coupling of mesitol (19) with bis(chloromethyl)mesitol (20) and bis(chloromethyl)mesitylene (21) in nitroethane in the presence of SnCl4 affords metacyclophanes 6 and 7-10, respectively, possessing extra-annular hydroxyl groups. Metacyclophanes 12 and 14, which hold one or two pairs of carboxyl groups in the distal positions, have been obtained from the appropriate distal diol 8 and tetrol 6 by treatment with tert-butyl bromoacetate followed by basic hydrolysis. Functionalized molecular frameworks, such as 15 and 18, have been also prepared in high yield by direct methods. The H-1 NMR spectral characteristics of 1,3-alternate metacyclophanes synthesized are briefly discussed. The structures of mono-, tri-, and tetrahydroxy metacyclophanes 10, 7, and 6, respectively, have been determined by X-ray crystallography. All three macrocycles have very similar 1,3-alternate-biconic conformations with approximate 42mBAR symmetry. Molecules 10 and 7 are isomorphous, and the lone hydroxyl group in 10 and the three hydroxyl groups in 7 are disordered over four possible sites. A toluene of solvation is docked against the molecular cavity in both 10 and 7. Compound 6 has crystallographic 2-fold symmetry and what would have been voids in the crystal lattice are occupied by disordered solvent molecules.

  DOI：

  10.1021/jo00052a023

文献信息

• Mesitylene-derived 1,3-alternate [1.1.1.1]metacyclophanes
  作者：Sebastiano Pappalardo、George Ferguson、John F. Gallagher

  DOI：10.1021/jo00052a023

  日期：1992.12

  Synthetic procedures to conformationally immobile 1,3-alternate [1.1.1.1]metacyclophanes based on mesitylene units are described. Coupling of mesitol (19) with bis(chloromethyl)mesitol (20) and bis(chloromethyl)mesitylene (21) in nitroethane in the presence of SnCl4 affords metacyclophanes 6 and 7-10, respectively, possessing extra-annular hydroxyl groups. Metacyclophanes 12 and 14, which hold one or two pairs of carboxyl groups in the distal positions, have been obtained from the appropriate distal diol 8 and tetrol 6 by treatment with tert-butyl bromoacetate followed by basic hydrolysis. Functionalized molecular frameworks, such as 15 and 18, have been also prepared in high yield by direct methods. The H-1 NMR spectral characteristics of 1,3-alternate metacyclophanes synthesized are briefly discussed. The structures of mono-, tri-, and tetrahydroxy metacyclophanes 10, 7, and 6, respectively, have been determined by X-ray crystallography. All three macrocycles have very similar 1,3-alternate-biconic conformations with approximate 42mBAR symmetry. Molecules 10 and 7 are isomorphous, and the lone hydroxyl group in 10 and the three hydroxyl groups in 7 are disordered over four possible sites. A toluene of solvation is docked against the molecular cavity in both 10 and 7. Compound 6 has crystallographic 2-fold symmetry and what would have been voids in the crystal lattice are occupied by disordered solvent molecules.