spiro-1,2,3,6-tetrahydropyrene> | 149296-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: spiro-1,2,3,6-tetrahydropyrene>
• 英文别名: spiro[cyclopentane-6,6'-[6H]-1,2,3,6-tetrahydropyrene]；spiro[2,3-dihydro-1H-pyrene-6,1'-cyclopentane]
• CAS: 149296-31-1
• 化学式: C₂₀H₂₀
• 分子量: 260.379
• InChiKey: LCWPILNGLHBDCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  spiro-1,2,3,6-tetrahydropyrene> 在 copper diacetate 、 二异丁基氢化铝 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 4.5h， 生成 1'-hydroxyspiro-1,2,3,6-tetrahydropyrene>
  参考文献：
  名称：

  Spectrometry and reactivity of the 1-hydropyrenyl anion

  摘要：

  A study of the charge distribution in the 1-hydropyrenyl anion (2-), and of its regioselectivity toward electrophilic attack was undertaken. In order to obtain reliable information on the reactive positions in 2-, a model with the same conjugated system was prepared, which has its 1-position fixed with a spirocyclopentane ring. Highly resolved H-1 and C-13 NMR spectra of this spiro[cyclopentane-1,1'-[1H]pyrenyl] anion (1-) and of 2- were obtained. These spectra could be completely assigned by means of COSY, NOESY, and 2D H-1-C-13 COSY techniques. According to the C-13 NMR measurements, 5-C of 1- and 2- bears the highest negative charge. The results of PM3 semiempirical calculations support this finding and, furthermore, a large HOMO coefficient was calculated at the quaternary 3a-C of 2-, suggesting that this position is susceptible toward attack by soft electrophiles. In full agreement with the C-13 NMR and PM3 results, 5-C of 1- and 2- show the highest reactivity toward electrophilic attack, while the quaternary 3a-C of 1- and 2- is attacked by soft electrophiles. These new results contradict earlier findings because until now, carbon atom 9-C of the 1-hydropyrenyl anion (2-) was assumed to be the most reactive position, and soft electrophiles were thought to attack 10a-C of 2-.

  DOI：

  10.1021/jo00063a029
• 作为产物：
  描述：

  芘 、 alkaline earth salt of/the/ methylsulfuric acid 在 正丁基锂 、 sodium 、 异丙醇 作用下， 以 四氢呋喃 、 氨 为溶剂， 生成 spiro-1,2,3,6-tetrahydropyrene>
  参考文献：
  名称：

  苯二甲酰基阴离子的光谱法和反应性

  摘要：

  为了研究该共轭阴离子对甲基和甲氧基的扰动，制备了芳香族奇数交替的菲烯基阴离子及其许多衍生物。通过1 H和13 C NMR光谱，烷基化实验和半经验计算研究了共轭阴离子。发现带电碳原子上的取代基扰乱了整个共轭体系，而无活性（不带电）碳原子上的取代基对取代基邻位的影响很大。

  DOI：

  10.1002/poc.610070605