1r,2t-Di-p-tosyloxymethyl-3c,4t-diphenyl-cyclobutan | 103397-59-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 环丁烷木脂素
• 英文名称: 1r,2t-Di-p-tosyloxymethyl-3c,4t-diphenyl-cyclobutan
• 英文别名: 1-ref,2-cis-Bis-(p-tosyloxymethyl)-3-trans,4-trans-diphenyl-cyclobutan；1,2-Bis-(p-toluolsulfonyloxymethyl)-3,4-diphenylcyclobutan
• CAS: 103397-59-7
• 化学式: C₃₂H₃₂O₆S₂
• 分子量: 576.734
• InChiKey: NEYOPKCSKVNFFL-UTRLAFKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  86.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  正丁基锂 、 1r,2t-Di-p-tosyloxymethyl-3c,4t-diphenyl-cyclobutan 在 copper(l) iodide 作用下， 生成
  参考文献：
  名称：

  Aggregate Formation and Photoreactivity in Phospholipid Vesicles and Langmuir-Blodgett Multilayers: Topologically Controlled Photodimerization of Amphiphilic Styrenes

  摘要：

  The amphiphilic styrene fatty acid 1 and its corresponding phosphatidylcholine derivative 2 have been found to exhibit aggregate formation and topologically controlled photodimerization in Langmuir-Blodgett (LB) assemblies and phospholipid vesicles, respectively. For both compounds, formation of the beta or syn, head-to-head photodimer is the chief photoreaction observed upon irradiation in the assemblies; a trace of the cis styrene is observed on irradiation in the phospholipid vesicles. Changes in the absorption spectrum and a lack of fluorescence in the assemblies, compared to dilute organic solutions, suggest that 1 and 2 exist as ''H'' aggregates in both the LB films and vesicles. Monte Carlo simulations suggest that the most stable structure in a monolayer is a simple translation aggregate. Energy minimization gives a cross sectional area in good agreement with that measured for films at the air-water interface. The calculated structure has nearest neighbor separation within the ''magic distance'' for solid state photodimerization of 4.10 Angstrom. The relatively small calculated tilt angle suggests that dimers can be formed without substantial reorganization. The lambda(max) for the aggregate estimated by an extended dipole calculation shows good agreement with the measured absorption maximum. Vesicles of 2, either pure or with excess saturated phospholipid, give topologically controlled formation of the beta dimer via photolysis of an aggregated form.

  DOI：

  10.1021/ja00102a012
• 作为产物：
  描述：

  β-truxinic acid 在 吡啶 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1r,2t-Di-p-tosyloxymethyl-3c,4t-diphenyl-cyclobutan
  参考文献：
  名称：

  Aggregate Formation and Photoreactivity in Phospholipid Vesicles and Langmuir-Blodgett Multilayers: Topologically Controlled Photodimerization of Amphiphilic Styrenes

  摘要：

  The amphiphilic styrene fatty acid 1 and its corresponding phosphatidylcholine derivative 2 have been found to exhibit aggregate formation and topologically controlled photodimerization in Langmuir-Blodgett (LB) assemblies and phospholipid vesicles, respectively. For both compounds, formation of the beta or syn, head-to-head photodimer is the chief photoreaction observed upon irradiation in the assemblies; a trace of the cis styrene is observed on irradiation in the phospholipid vesicles. Changes in the absorption spectrum and a lack of fluorescence in the assemblies, compared to dilute organic solutions, suggest that 1 and 2 exist as ''H'' aggregates in both the LB films and vesicles. Monte Carlo simulations suggest that the most stable structure in a monolayer is a simple translation aggregate. Energy minimization gives a cross sectional area in good agreement with that measured for films at the air-water interface. The calculated structure has nearest neighbor separation within the ''magic distance'' for solid state photodimerization of 4.10 Angstrom. The relatively small calculated tilt angle suggests that dimers can be formed without substantial reorganization. The lambda(max) for the aggregate estimated by an extended dipole calculation shows good agreement with the measured absorption maximum. Vesicles of 2, either pure or with excess saturated phospholipid, give topologically controlled formation of the beta dimer via photolysis of an aggregated form.

  DOI：

  10.1021/ja00102a012

文献信息

• Cyclobutane Diolefins. 1,2-Diphenyldimethylenecyclobutane^1,2
  作者：A. T. Blomouist、Yvonne C. Meinwald

  DOI：10.1021/ja01499a036

  日期：1960.7