1,6-bis(4-formylbuta-1,3-dienyl)cyclohepta-1,3,5-triene | 112489-37-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-bis(4-formylbuta-1,3-dienyl)cyclohepta-1,3,5-triene
• 英文别名: (2E,4E)-5-[6-[(1E,3E)-5-oxopenta-1,3-dienyl]cyclohepta-1,3,5-trien-1-yl]penta-2,4-dienal
• CAS: 112489-37-9
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: SELMZXYVCRGPOM-BWZMWZRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6-bis(4-formylbuta-1,3-dienyl)cyclohepta-1,3,5-triene 在 盐酸 、 n-butyllithium hexane 、 copper diacetate 、 乙醇锂 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 17,18,19,20-tetradehydro-16,21-dimethyl-1,6-methano<30>annulene
  参考文献：
  名称：

  Ojima, Juro; Fujita, Satoshi; Masamuto, Masayuki, Journal of the Chemical Society. Perkin transactions I, 1988, p. 385 - 394

  摘要：

  DOI：
• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 1,6-bis(4-formylbuta-1,3-dienyl)cyclohepta-1,3,5-triene
  参考文献：
  名称：

  Ojima, Juro; Fujita, Satoshi; Masamuto, Masayuki, Journal of the Chemical Society. Perkin transactions I, 1988, p. 385 - 394

  摘要：

  DOI：

文献信息

• Synthesis, Structural and Conformational Analysis of Methanohomo(15)annulene and Methanohomo(19)annulene.
  作者：Hiroyuki Higuchi、Tamae Hashimoto、Kaori Nakafuku、Juro Ojima、Gaku Yamamoto

  DOI：10.1246/bcsj.66.294

  日期：——

  Methanohomo[15]annulene and methanohomo[19]annulene were synthesized by the Wittig reactions of 1,3-bis(triphenylphosphonio)propane dibromide with 1,6-bis(2-formylvinyl)- and 1,6-bis(4-formyl-1,3-butadienyl)-1,3,5-cycloheptatriene, respectively. Conformational properties of these homoannulenes are discussed. Attempts to convert these homoannulenes into the corresponding 14π- and 18π-methanoannulenyl cations were unsuccessful.

  通过 1,3-双(三苯基膦)丙烷二溴化物与 1,6-双(2-甲酰基乙烯基)-和 1,6-双(4-甲酰基-1,3-丁二烯基)-1,3,5-环庚三烯的维蒂希反应，分别合成了 Methanohomo[15]annulene 和 methanohomo[19]annulene 。本文讨论了这些均苯烯烃的构象特性。将这些均苯烯烃转化为相应的 14π- 和 18π- 甲基苯烯烃阳离子的尝试并不成功。
• Unusual formation of a methano-bridged didehydro[20]annulenedione. A highly diatropic, dicationic 18π-electron species in D₂SO₄
  作者：Gaku Yamamoto、Hiroyuki Higuchi、Kaori Asano、Jūro Ojima

  DOI：10.1039/c39930000698

  日期：——

  An intramolecular coupling of 1,6-bis(5-oxohepta-1,3-dien-6-ynyl)cyclohepta-1,3,5-triene under Glaser conditions affords 12,15-dichloro-13,14-didehydro-1,6-methano[20]annulene-11,16-dione, which exhibits strong diatropicity in D2SO4, suggesting the formation of the highly delocalized dicationic species.

  在格拉塞条件下，1,6-双（5-氧代庚烷-1,3-二烯-6-炔基）环庚烷-1,3,5-三烯发生分子内偶联，生成 12,15-二氯-13,14-二脱氢-1,6-甲桥[20]庚烯-11,16-二酮。
• The highly stable 1,6-methanotetradehydro-[26]-, -[28]-, -[30]-, -[32]-, -[34]-, and -[38]-annulenes. Limiting ring size for dia- and para-tropicity
  作者：J?ro Ojima、Satoshi Fujita、Masayuki Masumoto、Emiko Ejiri、Tadahito Kato、Shigeyasu Kuroda、Yoshihiko Nozawa、Hitoshi Tatemitsu

  DOI：10.1039/c39870000534

  日期：——

  The title annulenes have been synthesized and their 1H n.m.r. spectra indicate that the [28]- and [34]-annulenes as well as the lower-membered ones can sustain a ring current.

  标题环已合成，其1 H nmr光谱表明[28]-和[34]-环以及低级环可以维持环电流。
• Synthesis and Properties of Methano-Bridged Thia[15]-, Thia[17]-, and Thia[19]annulenes
  作者：Shigeyasu Kuroda、Yoshihiko Nozawa、Yoshiharu Yoneyama、Satoshi Fujita、Kazuhiro Yanagihara、Juro Ojima

  DOI：10.1246/cl.1987.1679

  日期：1987.8.5

  Title annulenes have been synthesized through a double Wittig reaction between the vinylogous dicarbaldehydes of 1,6-diformylcycloheptatriene and bis[(triphenylphosphonio)methyl]sulfide dibromide, and their 1H NMR spectra were examined proving that the thia[17]- and - [19]annulenes sustain ring current, while the thia-[15]annulene does not.

  标题环烯已通过 1,6-二甲酰基环庚三烯的乙烯基二甲醛和双[（三苯基膦）甲基] 硫化物二溴化物之间的双重 Wittig 反应合成，并检查了它们的 1H NMR 光谱，证明硫杂 [17]- 和 - [19 ]annulenes 维持环电流，而 thia-[15]annulene 不。
• Syntheses and properties of methano-bridged dichlorodidehydro-[16]-, -[20]-and-[24]-annulenediones
  作者：Hiroyuki Higuchi、Kaori Asano、J?ro Ojima、Koji Yamamoto、Toshikatsu Yoshida、Tomohiro Adachi、Gaku Yamamoto

  DOI：10.1039/p19940001453

  日期：——

  Bisethynylation of the vinylogous dialdehydes of cyclohepta-1.3,5-triene-1,6-dicarbaldehyde with ethynylmagnesium bromide followed by oxidation of the resulted diols afforded the diacetylenic diketones. Intramolecular oxidative coupling of these diketones under the Glaser conditions unexpectedly afforded three annulenediones with a 1,4-dichlorobutatriene moiety. The unusual structures were confirmed by X-ray crystallographic analysis of 10,13-dichloro-11.12-didehydro-1,6methano[16]annulene-9,1 4-dione. These annulenediones exhibited strong diatropicity in D2SO4 due to the dicationic 14 pi-, 18 pi- and 22 pi-electron species and their diatropicities were shown to increase with increasing ring size.