(1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-1-[(tert-butyldimethylsilyloxy)methyl]-15-ethenyl-quinquecyclopropane | 335248-49-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-1-[(tert-butyldimethylsilyloxy)methyl]-15-ethenyl-quinquecyclopropane
• 英文别名: tert-butyl-[[(1R,2S)-2-[(1R,2R)-2-[(1R,2R)-2-[(1R,2R)-2-[(1R,2S)-2-ethenylcyclopropyl]cyclopropyl]cyclopropyl]cyclopropyl]cyclopropyl]methoxy]-dimethylsilane
• CAS: 335248-49-2
• 化学式: C₂₄H₄₀OSi
• 分子量: 372.666
• InChiKey: AKZPKPZJPSGQBE-JEUMPPENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-1-[(tert-butyldimethylsilyloxy)methyl]-15-ethenyl-quinquecyclopropane 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， 反应 1.0h， 生成 (1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-15-ethenyl-1-quinquecyclopropanemethyl 4-ethenylbenzoate
  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：

  亚甲基三苯基膦烷 、 以 四氢呋喃 为溶剂， 反应 1.0h， 以74 mg的产率得到(1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-1-[(tert-butyldimethylsilyloxy)methyl]-15-ethenyl-quinquecyclopropane
  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

• 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.