4,4'-[nonane-1,9-diylbis(oxy)]bis[benzenemethanol]

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,4'-[nonane-1,9-diylbis(oxy)]bis[benzenemethanol]
• 英文别名: 1,9-bis[(4-hydroxymethyl)phenoxy]nonane；[4-[9-[4-(Hydroxymethyl)phenoxy]nonoxy]phenyl]methanol；[4-[9-[4-(hydroxymethyl)phenoxy]nonoxy]phenyl]methanol
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: PVSIDFCKWIPFNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-[nonane-1,9-diylbis(oxy)]bis[benzenemethanol] 在 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,1'-[nonane-1,9-diylbis(oxy)]bis[4-(bromomethyl)benzene]
  参考文献：
  名称：

  Analysis and Improvement of an Anion-Templated Rotaxane Synthesis

  摘要：

  A series of new rotaxanes with axles different in length was prepared. Following the synthetic protocol utilizing a known anion template effect (Scheme 1), surprisingly low yields in the order of 2 - 5% were obtained (Scheme 3), which furthermore significantly depended on the nature of the stopper (Fig. 1). Variations in the synthetic procedures and computational results from Monte Carlo simulations allowed us to analyze the origin of these findings: The rotaxane wheel 3 acts as a noncovalently bound 'protecting group' for the stopper nucleophile. The protection of the nucleophilic phenolate O-atom depends much on the steric demands of the stoppers (see 2 vs. 10) which induce different conformations of the wheel. Based on this model. an improved synthetic scheme is suggested.

  DOI：

  10.1002/1522-2675(200206)85:6<1578::aid-hlca1578>3.0.co;2-l
• 作为产物：
  描述：

  4,4'-[1,9-壬烷二基二(氧基)]二苯甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 4.0h， 生成 4,4'-[nonane-1,9-diylbis(oxy)]bis[benzenemethanol]
  参考文献：
  名称：

  27 至 39 位吡啶大环化合物

  摘要：

  已经通过威廉姆森醚合成或闭环复分解合成了一组 27 至 39 元吡啶大环 2 和 3。吡啶是 2,6-二取代的以允许内相互作用。除了长度之外，脂肪链的性质也不同：饱和（2）和不饱和（3）。

  DOI：

  10.1002/ejoc.201000505

文献信息

• US9310681B2
  申请人：——

  公开号：US9310681B2

  公开（公告）日：2016-04-12
• 27- to 39-Membered Pyridine Macrocycles
  作者：Ulrich Lüning、Ellen Mak、Melanie Zindler、Britta Hartkopf、Rainer Herges

  DOI：10.1002/ejoc.201000505

  日期：2010.9

  A set of 27- to 39-membered pyridine macrocycles 2 and 3 has been synthesized by Williamson ether synthesis or ring-closing metathesis. The pyridines are 2,6-disubstituted to allow endo interactions. In addition to the length, also the nature of the aliphatic chain was varied: saturated (2) and unsaturated (3).

  已经通过威廉姆森醚合成或闭环复分解合成了一组 27 至 39 元吡啶大环 2 和 3。吡啶是 2,6-二取代的以允许内相互作用。除了长度之外，脂肪链的性质也不同：饱和（2）和不饱和（3）。
• Analysis and Improvement of an Anion-Templated Rotaxane Synthesis
  作者：Christoph A. Schalley、Gabriele Silva、Carl Friedrich Nising、Petra Linnartz

  DOI：10.1002/1522-2675(200206)85:6<1578::aid-hlca1578>3.0.co;2-l

  日期：2002.6

  A series of new rotaxanes with axles different in length was prepared. Following the synthetic protocol utilizing a known anion template effect (Scheme 1), surprisingly low yields in the order of 2 - 5% were obtained (Scheme 3), which furthermore significantly depended on the nature of the stopper (Fig. 1). Variations in the synthetic procedures and computational results from Monte Carlo simulations allowed us to analyze the origin of these findings: The rotaxane wheel 3 acts as a noncovalently bound 'protecting group' for the stopper nucleophile. The protection of the nucleophilic phenolate O-atom depends much on the steric demands of the stoppers (see 2 vs. 10) which induce different conformations of the wheel. Based on this model. an improved synthetic scheme is suggested.