12-methylene-1,10-dioxa-4,7-dithiacyclotridecane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12-methylene-1,10-dioxa-4,7-dithiacyclotridecane
• 化学式: C₁₀H₁₈O₂S₂
• 分子量: 234.384
• InChiKey: QCZGBJLZELFBDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  12-methylene-1,10-dioxa-4,7-dithiacyclotridecane 在 盐酸 、 锂硼氢 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 1,2-bis[((1,10-dioxa-4,7-dithiacyclotridecan-12-yl)methoxy)methyl]benzene
  参考文献：
  名称：

  Structurally original oxathioethers macrocycles containing an exocyclic double-bond: synthesis, characterization, reactivity, and coordination

  摘要：

  New oxathioethers macrocycles have been synthesized and characterized. Each macrocycle consists in structurally defined ether and thioether moieties and an exocyclic double-bond (2a-c) or a hydroxymethyl group (3a-c). Macrocycles (2a-c) have been synthesized by reaction of dianions of thioethers dials (1a-c) with 3-chloro-2-chloromethylprop-1-ene. Their hydroboration/oxidation led to corresponding primary alcohols (3a-c). Structures of compounds (2b) and (3a) have been determined by X-ray diffraction. The reactivity of the hydroxyl group allowed the preparation of oxathioethers macrocycles bearing a polyether chain or a benzyl group (4a,b) and the synthesis of new bicyclic sandwich-type compounds (5a,b). The ability of these functionalized macrocycles to coordinate to palladium has been investigated. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.082
• 作为产物：
  描述：

  3-氯-2-氯甲基丙烯 、 3,6-二硫杂-1,8-辛二醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以17%的产率得到12-methylene-1,10-dioxa-4,7-dithiacyclotridecane
  参考文献：
  名称：

  Structurally original oxathioethers macrocycles containing an exocyclic double-bond: synthesis, characterization, reactivity, and coordination

  摘要：

  New oxathioethers macrocycles have been synthesized and characterized. Each macrocycle consists in structurally defined ether and thioether moieties and an exocyclic double-bond (2a-c) or a hydroxymethyl group (3a-c). Macrocycles (2a-c) have been synthesized by reaction of dianions of thioethers dials (1a-c) with 3-chloro-2-chloromethylprop-1-ene. Their hydroboration/oxidation led to corresponding primary alcohols (3a-c). Structures of compounds (2b) and (3a) have been determined by X-ray diffraction. The reactivity of the hydroxyl group allowed the preparation of oxathioethers macrocycles bearing a polyether chain or a benzyl group (4a,b) and the synthesis of new bicyclic sandwich-type compounds (5a,b). The ability of these functionalized macrocycles to coordinate to palladium has been investigated. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.082

文献信息

• Functionalized oxathiacrown macrocycles: Synthesis, characterization and coordination to palladium(II), ruthenium(II) and copper(I)
  作者：Guillaume Carel、David Madec、Alina Saponar、Nathalie Saffon、Gabriela Nemes、Ghassoub Rima、Annie Castel

  DOI：10.1016/j.jorganchem.2014.01.002

  日期：2014.4

  New oxathiacrown macrocycles with exocyclic double bond 1 and 2 were synthesized and characterized. Their coordination behavior with soft transition metals is investigated. Reaction of 1 with PdCl2 afforded exo-coordinated complex 3 with the two S-donor atoms. With RuCl2(PPh3)(3), the macrocyclic ligand 1 is bonded through three donor atoms (two sulfur and one oxygen) to the ruthenium center in a facial coordination mode. By contrast, double and single-stranded one dimensional (1D) coordination polymers were obtained by reaction of CuBr with macrocycles 1 and 2. All complexes were spectroscopically characterized and their structure was secured by X-ray diffraction analysis. (C) 2014 Elsevier B. V. All rights reserved.
• Structurally original oxathioethers macrocycles containing an exocyclic double-bond: synthesis, characterization, reactivity, and coordination
  作者：Guillaume Carel、Alina Saponar、Nathalie Saffon、Marc Vedrenne、Stéphane Massou、Gabriela Nemes、Ghassoub Rima、David Madec、Annie Castel

  DOI：10.1016/j.tet.2014.06.082

  日期：2014.9

  New oxathioethers macrocycles have been synthesized and characterized. Each macrocycle consists in structurally defined ether and thioether moieties and an exocyclic double-bond (2a-c) or a hydroxymethyl group (3a-c). Macrocycles (2a-c) have been synthesized by reaction of dianions of thioethers dials (1a-c) with 3-chloro-2-chloromethylprop-1-ene. Their hydroboration/oxidation led to corresponding primary alcohols (3a-c). Structures of compounds (2b) and (3a) have been determined by X-ray diffraction. The reactivity of the hydroxyl group allowed the preparation of oxathioethers macrocycles bearing a polyether chain or a benzyl group (4a,b) and the synthesis of new bicyclic sandwich-type compounds (5a,b). The ability of these functionalized macrocycles to coordinate to palladium has been investigated. (C) 2014 Elsevier Ltd. All rights reserved.