15-methylene-1,13-dioxa-4,7,10-trithiacyclohexadecane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 15-methylene-1,13-dioxa-4,7,10-trithiacyclohexadecane
• 英文别名: 15-Methylidene-1,13-dioxa-4,7,10-trithiacyclohexadecane；15-methylidene-1,13-dioxa-4,7,10-trithiacyclohexadecane
• 化学式: C₁₂H₂₂O₂S₃
• 分子量: 294.503
• InChiKey: AXPRSRNYTCKXFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  94.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  15-methylene-1,13-dioxa-4,7,10-trithiacyclohexadecane 在 盐酸 、 锂硼氢 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 2.0h， 以45%的产率得到(1,13-dioxa-4,7,10-trithiacyclohexadecan-15-yl)methanol
  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 、 2,2'-[硫烷二基二(2,1-乙二基硫烷二基)]二乙醇 在 sodium 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以17%的产率得到15-methylene-1,13-dioxa-4,7,10-trithiacyclohexadecane
  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

• 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.