α,α'-bis<3,5-bis(hydroxymethyl)phenoxy>-o-xylene | 177798-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: α,α'-bis<3,5-bis(hydroxymethyl)phenoxy>-o-xylene
• 英文别名: [3-[[2-[[3,5-Bis(hydroxymethyl)phenoxy]methyl]phenyl]methoxy]-5-(hydroxymethyl)phenyl]methanol
• CAS: 177798-51-5
• 化学式: C₂₄H₂₆O₆
• 分子量: 410.467
• InChiKey: NNQITDCNAXUTEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α,α'-bis<3,5-bis(hydroxymethyl)phenoxy>-o-xylene 在 吡啶 、 氢氧化钾 、 氯化亚砜 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 生成 62,68-dibromo-49,58-dioxa-5,21,29,45-tetrathiaundecacyclo[23.23.10.27,10.216,19.231,34.240,43.13,47.111,15.123,27.135,39.051,56]heptaconta-1(48),2,7(70),8,10(69),11(68),12,14,16(67),17,19(66),23,25,27(65),31,33,35,37,39(62),40,42,47(59),51,53,55,60,63-heptacosaene
  参考文献：
  名称：

  Synthesis of functionalised cyclophanes with cage structure; via an unusual termolecular collision

  摘要：

  Coupling of the tetrathiol 11 with two equivalents of the dibromide 6,7 and 8 under high dilution technique in the presence of KOH in benzene - ethanol afforded the cyclophanes 1a, 1c & 1b respectively. Similarly cyclophane 1d was obtained from the tetrathiol 11 and tetrabromide 9.

  DOI：

  10.1016/s0040-4039(00)61420-x
• 作为产物：
  描述：

  1,2-二(溴甲基)苯 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 α,α'-bis<3,5-bis(hydroxymethyl)phenoxy>-o-xylene
  参考文献：
  名称：

  3-烷氧基苯卟啉的合成、光谱性质和金属化

  摘要：

  由 5-羟基间苯二甲酸二甲酯分三步制备了一系列 5-烷氧基-1,3-苯二甲醛和相关二聚体。酸催化二醛与三吡喃二甲酸缩合，然后用 2,3-二氯-5,6-二氰基-1,4-苯醌氧化，得到了良好产率的 3-烷氧基苯卟啉，尽管二聚四醛未能得到可分离的类卟啉产品。质子核磁共振波谱没有显示出芳环电流，但三氟乙酸的添加导致了双阳离子的形成，表现出弱的双异性特征。 TFA 光谱滴定表明发生了逐步质子化，产生单阳离子和双阳离子物质。 3-烷氧基苯卟啉与乙酸镍(II)或乙酸钯(II)反应，得到相关的镍(II)或钯(II)络合物。这些稳定的有机金属衍生物表现出增强的均变性能，这对于钯 (II) 配合物最为明显。这些独特的卟啉类化合物提供了对苯卟啉性质的进一步了解。

  DOI：

  10.3390/molecules29081903

文献信息

• Synthesis and structural analysis of isomeric pyridinophanes and thiacyclophanes
  作者：Perumal Rajakumar、Manickam Dhanasekaran、Sivashanmugam Selvanayagam、Venkatachalam Rajakannan、Devadasan Velmurugan、Krishnan Ravikumar

  DOI：10.1016/j.tetlet.2004.12.033

  日期：2005.2

  A one-pot synthesis of structurally isomeric tetrathiacyclophanes through four-centre coupling reactions of suitable bromides and thiols is reported. The structures of the isomers were confirmed by spectroscopy and XRD analysis. Single crystal X-ray analysis reveals interestingly shaped molecular structures with large cavities. (C) 2004 Published by Elsevier Ltd.
• Synthesis of functionalised cyclophanes with cage structure; via an unusual termolecular collision
  作者：Perumal Rajakumar、Arunachalam Kannan

  DOI：10.1016/s0040-4039(00)61420-x

  日期：1993.12

  Coupling of the tetrathiol 11 with two equivalents of the dibromide 6,7 and 8 under high dilution technique in the presence of KOH in benzene - ethanol afforded the cyclophanes 1a, 1c & 1b respectively. Similarly cyclophane 1d was obtained from the tetrathiol 11 and tetrabromide 9.
• Synthesis of Cyclophanes with Intra-Annular Functionality and Cage Structure
  作者：Arunachalam Kannan、Perumal Rajakumar、V. Kabaleeswaran、S. S. Rajan

  DOI：10.1021/jo950957y

  日期：1996.1.1

  Cyclophanes of the type 1 and 2, with large cavity sizes, have been synthesized from the corresponding dichloride 8 or 8a and o-xylene-alpha,alpha'-dithiol (9), p-xylene-alpha,alpha'-dithiol (10), or m-terphenyldithiol (11). Similarly, cyclophanes of the type 3 with intra-annular functionality have been obtained by the coupling of the corresponding dithiol 15 or 19 and m-terphenyl dibromide 5, 5a, 5b, or 5c. With the aim of introducing multifunctionality, cyclophanes of the type 21 and 23 were prepared from 3,5-bis(mercaptomethyl)anisole or 3,5-bis(mercaptomethyl)phenol and the corresponding substituted m-terphenyl dibromide Bb or 5c. Cyclophanes 24, 24a, 24b, and 32, with a new type of cage structure, have been obtained by the coupling of the corresponding tetrathiol as with 2 equiv of the dibromides 5c, 5a, and 5b or 1 equiv of the tetrabromide 31, respectively. Further, the sodium salts of the cyclophanes 3c, 21, and 24b were completely characterized by H-1 NMR spectroscopy. XRD analysis of the cyclophane 21 revealed the presence of an ethanol molecule inside the cavity, indicating the facile formation of a host-guest complex.
• Synthesis, Spectroscopic Properties, and Metalation of 3-Alkoxybenziporphyrins
  作者：Rachel A. Tomlovich、Timothy D. Lash

  DOI：10.3390/molecules29081903

  日期：——

  characteristics. Spectroscopic titration with TFA demonstrated that stepwise protonation took place, generating monocationic and dicationic species. 3-Alkoxybenziporphyrins reacted with nickel(II) or palladium(II) acetate to give the related nickel(II) or palladium(II) complexes. These stable organometallic derivatives showed increased diatropic properties that were most pronounced for the palladium(II) complexes

  由 5-羟基间苯二甲酸二甲酯分三步制备了一系列 5-烷氧基-1,3-苯二甲醛和相关二聚体。酸催化二醛与三吡喃二甲酸缩合，然后用 2,3-二氯-5,6-二氰基-1,4-苯醌氧化，得到了良好产率的 3-烷氧基苯卟啉，尽管二聚四醛未能得到可分离的类卟啉产品。质子核磁共振波谱没有显示出芳环电流，但三氟乙酸的添加导致了双阳离子的形成，表现出弱的双异性特征。 TFA 光谱滴定表明发生了逐步质子化，产生单阳离子和双阳离子物质。 3-烷氧基苯卟啉与乙酸镍(II)或乙酸钯(II)反应，得到相关的镍(II)或钯(II)络合物。这些稳定的有机金属衍生物表现出增强的均变性能，这对于钯 (II) 配合物最为明显。这些独特的卟啉类化合物提供了对苯卟啉性质的进一步了解。