bis[2-(trimethylsilyl)ethyl] 1,4-benzenedicarboxylate | 335248-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis[2-(trimethylsilyl)ethyl] 1,4-benzenedicarboxylate
• 英文别名: Bis(2-trimethylsilylethyl) benzene-1,4-dicarboxylate
• CAS: 335248-33-4
• 化学式: C₁₈H₃₀O₄Si₂
• 分子量: 366.605
• InChiKey: HIYUROZVXJYVIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis[2-(trimethylsilyl)ethyl] 1,4-benzenedicarboxylate 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (1R,3S,4R,6S,7R,9R,10S,12R,13S,15R)-15-[(t-butyldimethylsilyloxy)methyl]-1-quinquecyclopropanemethyl 2-(trimethylsilyl)ethyl 1,4-benzenedicarboxylate
  参考文献：
  名称：

  Synthesis and Characterization of Coronanes:  Multicyclopropane-Fused Macrocyclic Arrays

  摘要：

  Stepwise macrocyclization of the all syn-trans-1,15-quinquecyclopropanedimethanol (4) with iso- and terephthaloyl chlorides and 4,4'-methanediyl-dibenzoic acid (28) gave the corresponding coronanes 22, 23, and 32. The same protocol was used with all syn-trans-1,21-septecyclopropanedimethanol (5) and 2,3-naphthalenedicarboxylic acid to obtain the macrolide 27. Direct macrocyclization of diol 4 and 1,10-phenanthroline-2,9-dicarbonyl chloride (33) and 2,2'-bipyridine-4,4'-dicarbonyl chloride (35) gave the coronanes 34 and 36, respectively. Ring closing metathesis (RCM) of the diene 42 using Cl-2(Cy3P)(2)Ru=CHPh (48) (Grubbs's catalyst) gave the macrocyclic lactone 45. The structures of coronanes 22, 23, 32, 34, 36, and 45 were confirmed by X-ray crystallographic studies which showed the cyclopropyl chain to adopt very differing conformations throughout the series. Several of the macrocycles have significant free pathways through their ring centers, and in the case of compound 34 there is a water molecule hydrogen bonded within the ring. This latter compound has the potential to act as a chiral ligand to metal centers.

  DOI：

  10.1021/jo001167d
• 作为产物：
  描述：

  2-(三甲硅基)乙醇 、 对苯二甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到bis[2-(trimethylsilyl)ethyl] 1,4-benzenedicarboxylate
  参考文献：
  名称：

  Synthesis and Characterization of Coronanes:  Multicyclopropane-Fused Macrocyclic Arrays

  摘要：

  Stepwise macrocyclization of the all syn-trans-1,15-quinquecyclopropanedimethanol (4) with iso- and terephthaloyl chlorides and 4,4'-methanediyl-dibenzoic acid (28) gave the corresponding coronanes 22, 23, and 32. The same protocol was used with all syn-trans-1,21-septecyclopropanedimethanol (5) and 2,3-naphthalenedicarboxylic acid to obtain the macrolide 27. Direct macrocyclization of diol 4 and 1,10-phenanthroline-2,9-dicarbonyl chloride (33) and 2,2'-bipyridine-4,4'-dicarbonyl chloride (35) gave the coronanes 34 and 36, respectively. Ring closing metathesis (RCM) of the diene 42 using Cl-2(Cy3P)(2)Ru=CHPh (48) (Grubbs's catalyst) gave the macrocyclic lactone 45. The structures of coronanes 22, 23, 32, 34, 36, and 45 were confirmed by X-ray crystallographic studies which showed the cyclopropyl chain to adopt very differing conformations throughout the series. Several of the macrocycles have significant free pathways through their ring centers, and in the case of compound 34 there is a water molecule hydrogen bonded within the ring. This latter compound has the potential to act as a chiral ligand to metal centers.

  DOI：

  10.1021/jo001167d

文献信息

• Hetero Bi-Paddle-Wheel Coordination Networks: A New Synthetic Route to Rh-Containing Metal–Organic Frameworks
  作者：Satoshi Matsunaga、Ken-ichi Hasada、Kenji Sugiura、Naoki Kitamura、Yuri Kudo、Nanako Endo、Wasuke Mori

  DOI：10.1246/bcsj.20110361

  日期：2012.4.15

  We have successfully synthesized rhodium-containing MOFs with 1:1 abundance ratios of paddle-wheel units of Rh2 and Cu2/Zn2, i.e., [Rh2M2(1,4-bdc)4]·nSolvent (M = Cu: RhCu-DMF, RhCu-EtOH; M = Zn: RhZn-DMF; 1,4-bdc: 1,4-benzenedicarboxylate) by a novel synthetic method involving assembly of discrete paddle-wheel dirhodium(II) tetra(1,4-benzenedicarboxylate) with Cu2+ or Zn2+ ions. The diffraction patterns of these complexes were very similar to the predicted and experimental XRPD patterns reported for [Cu2(1,4-bdc)2]. This result indicates that this method enables the incorporation of coordinatively unsaturated noble-metal sites for the many reported MOFs with multi-carboxy ligands and paddle-wheel nodes.

  我们成功合成了Rh2和Cu2/Zn2的叶轮单元丰度比为1:1的含铑MOF，即[Rh2M2(1,4-bdc)4]·nSolvent (M = Cu: RhCu-DMF, RhCu-EtOH；M = Zn：RhZn-DMF；1,4-bdc：1,4-苯二甲酸），采用离散桨轮二铑（II）四（1,4-苯二甲酸）与 Cu2+ 组装的新型合成方法或 Zn2+ 离子。这些配合物的衍射图与​​ [Cu2(1,4-bdc)2] 报道的预测和实验 XRPD 图非常相似。这一结果表明，该方法能够为许多报道的具有多羧基配体和桨轮节点的 MOF 掺入配位不饱和贵金属位点。
• Synthesis and Characterization of Coronanes:  Multicyclopropane-Fused Macrocyclic Arrays
  作者：Anthony G. M. Barrett、Dieter Hamprecht、Rachel A. James、Mitsuru Ohkubo、Panayiotis A. Procopiou、Miguel A. Toledo、Andrew J. P. White、David J. Williams

  DOI：10.1021/jo001167d

  日期：2001.4.1

  Stepwise macrocyclization of the all syn-trans-1,15-quinquecyclopropanedimethanol (4) with iso- and terephthaloyl chlorides and 4,4'-methanediyl-dibenzoic acid (28) gave the corresponding coronanes 22, 23, and 32. The same protocol was used with all syn-trans-1,21-septecyclopropanedimethanol (5) and 2,3-naphthalenedicarboxylic acid to obtain the macrolide 27. Direct macrocyclization of diol 4 and 1,10-phenanthroline-2,9-dicarbonyl chloride (33) and 2,2'-bipyridine-4,4'-dicarbonyl chloride (35) gave the coronanes 34 and 36, respectively. Ring closing metathesis (RCM) of the diene 42 using Cl-2(Cy3P)(2)Ru=CHPh (48) (Grubbs's catalyst) gave the macrocyclic lactone 45. The structures of coronanes 22, 23, 32, 34, 36, and 45 were confirmed by X-ray crystallographic studies which showed the cyclopropyl chain to adopt very differing conformations throughout the series. Several of the macrocycles have significant free pathways through their ring centers, and in the case of compound 34 there is a water molecule hydrogen bonded within the ring. This latter compound has the potential to act as a chiral ligand to metal centers.