(19R,20R)-19,20-dimethyl-21-oxahexacyclo[10.6.2.13,6.02,7.09,19.016,20]henicosa-1,4,7,9,11,13,15,17-octaene | 138590-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (19R,20R)-19,20-dimethyl-21-oxahexacyclo[10.6.2.13,6.02,7.09,19.016,20]henicosa-1,4,7,9,11,13,15,17-octaene
• CAS: 138590-19-9
• 化学式: C₂₂H₁₈O
• 分子量: 298.384
• InChiKey: YDMQRKJDVKRBLX-SLMMIHQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (19R,20R)-19,20-dimethyl-21-oxahexacyclo[10.6.2.13,6.02,7.09,19.016,20]henicosa-1,4,7,9,11,13,15,17-octaene 在 3,6-二-2-吡啶基-1,2,4,5-四嗪 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以78%的产率得到trans-11b,11c-dimethyl-11b,11c-dihydropereno<1,2-c>furan
  参考文献：
  名称：

  An Experimental Estimation of Aromaticity Relative to That of Benzene. The Synthesis and NMR Properties of a Series of Highly Annelated Dimethyldihydropyrenes: Bridged Benzannulenes

  摘要：

  The synthesis of 13 trans-dimethyldihydropyrenes (bridged [14]annulenes) fused to one or more benzene, naphthalene, phenanthrene, phenalene, or quinoxaline rings and 6 cis-dihydropyrene derivatives from benzenoid precursors using either a thiacyclophane route or an electrocyclic addition of a furan to an annulyne followed by deoxygenation is reported. Their H-1 NMR spectra are studied in detail to obtain correlations between (3)J(H,H) coupling constants and the internal methyl proton chemical shifts and also between the latter and the more distant external annulene ring proton shifts. These linear correlations are then used to obtain a relationship between the relative aromaticity of benzene and the fused ring in question, such that the aromaticity of the fused ring can be estimated relative to that of a benzene ring simply from a measurement of chemical shift in the fused annulene.

  DOI：

  10.1021/ja00110a008
• 作为产物：
  描述：

  呋喃 、 2-Brom-trans-10b,10c-dimethyl-10b,10c-dihydropyren 在 potassium tert-butylate 、 sodium amide 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以62%的产率得到(19R,20R)-19,20-dimethyl-21-oxahexacyclo[10.6.2.13,6.02,7.09,19.016,20]henicosa-1,4,7,9,11,13,15,17-octaene
  参考文献：
  名称：

  The synthesis and trapping of the first [14]annulyne with benzyne like reactivity. A fast route to several annelated bridged annulenes.

  摘要：

  DOI：

  10.1016/s0040-4039(00)98049-3

文献信息

• Bond Alternation in Azulenes
  作者：Yingchun Lu、David M. Lemal、Jerry P. Jasinski

  DOI：10.1021/ja984113i

  日期：2000.3.1

  6-Azulyne, the first azulyne to be prepared, has been trapped with furan to give an adduct whose crystal structure reveals marked bond alternation in the azulene π system. The double bond in the furan moiety is responsible in part for the bond localization, as hydrogenation of that bond attenuates the effect. The regiochemistry of electrophilic attack on the adduct has been examined briefly, with results contrary

  5,6-Azulyne 是第一个制备的 Azulyne，已被呋喃捕获，得到一种加合物，其晶体结构显示出在 azulene π 系统中的显着键交替。呋喃部分中的双键部分负责键的定位，因为该键的氢化减弱了效果。对加合物的亲电攻击的区域化学进行了简要检查，结果与前沿轨道理论的预测相反。量子力学计算已经阐明了这些现象。
• The synthesis and reliable estimate of aromaticity in a diatropic, bridged, oxa[17]annulene.
  作者：Reginald H. Mitchell、Pengzu Zhou

  DOI：10.1016/0040-4039(91)80157-2

  日期：1991.10

  The bridged oxa[17]annulene, 7, has been synthesised and shown to have 11–16% of the ring current of the parent annulene, which is the first reliable experimental estimate of aromaticity of an oxa-annulene.

  桥联的氧杂[17]环戊烯7已被合成，并显示出其母体环的环电流的11–16％，这是对氧杂-环戊烯芳香性的第一个可靠的实验估计。