9,10-Dihydro-9,10-ethanoanthracene-11-methanol P-tosylate | 4427-38-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-Dihydro-9,10-ethanoanthracene-11-methanol P-tosylate
• 英文别名: 15-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenylmethyl 4-methylbenzenesulfonate
• CAS: 4427-38-7
• 化学式: C₂₄H₂₂O₃S
• 分子量: 390.503
• InChiKey: VKDJTAROTSLGAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  potassium cyanide 、 9,10-Dihydro-9,10-ethanoanthracene-11-methanol P-tosylate 以 二甲基亚砜 为溶剂， 反应 24.0h， 以98%的产率得到11-Cyanomethyl-9,10-dihydro-9,10-aethano-anthracen
  参考文献：
  名称：

  Rhodium(I)-Catalyzed Intramolecular Ene Reaction of Vinylidenecyclopropanes and Alkenes for the Formation of Bicyclo[5.1.0]octylenes

  摘要：

  An efficient catalytic system for the intramolecular ene reaction of allene and alkene of diarylvinylidenecyclopropanes has been established. The reaction was achieved by using [RhCl(CO)(2)](2) as the catalyst In co-solvents of toluene and acetonitrile. MeCN was found to play a crucial role in controlling the reaction toward formation of bicyclo[5.1.0]octylene derivatives. An alternative system consisting of [RhCl(CO)(2)](2) and toluene in the absence of MeCN was found to give [2 + 2] cycloaddition adducts. The structures have been unambiguously determined by X-ray structural analysis. Deuterium labeling experiments were conducted to confirm the mechanism hypothesis.

  DOI：

  10.1021/ol902505p
• 作为产物：
  描述：

  7-Dibenzobicyclo<2.2.2>octadienylcarbinol 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到9,10-Dihydro-9,10-ethanoanthracene-11-methanol P-tosylate
  参考文献：
  名称：

  Rhodium(I)-Catalyzed Intramolecular Ene Reaction of Vinylidenecyclopropanes and Alkenes for the Formation of Bicyclo[5.1.0]octylenes

  摘要：

  An efficient catalytic system for the intramolecular ene reaction of allene and alkene of diarylvinylidenecyclopropanes has been established. The reaction was achieved by using [RhCl(CO)(2)](2) as the catalyst In co-solvents of toluene and acetonitrile. MeCN was found to play a crucial role in controlling the reaction toward formation of bicyclo[5.1.0]octylene derivatives. An alternative system consisting of [RhCl(CO)(2)](2) and toluene in the absence of MeCN was found to give [2 + 2] cycloaddition adducts. The structures have been unambiguously determined by X-ray structural analysis. Deuterium labeling experiments were conducted to confirm the mechanism hypothesis.

  DOI：

  10.1021/ol902505p

文献信息

• Bridged polycyclic compounds. 85. Cationic rearrangements accompanying heterolysis of 7-dibenzobicyclo[2.2.2]octadienylcarbinyl derivatives
  作者：Stanley J. Cristol、Gwendolyn O. Mayo、Jan P. Kochansky

  DOI：10.1021/jo00427a005

  日期：1977.4
• Rhodium(I)-Catalyzed Intramolecular Ene Reaction of Vinylidenecyclopropanes and Alkenes for the Formation of Bicyclo[5.1.0]octylenes
  作者：Wei Li、Wei Yuan、Min Shi、Erik Hernandez、Guigen Li

  DOI：10.1021/ol902505p

  日期：2010.1.1

  An efficient catalytic system for the intramolecular ene reaction of allene and alkene of diarylvinylidenecyclopropanes has been established. The reaction was achieved by using [RhCl(CO)(2)](2) as the catalyst In co-solvents of toluene and acetonitrile. MeCN was found to play a crucial role in controlling the reaction toward formation of bicyclo[5.1.0]octylene derivatives. An alternative system consisting of [RhCl(CO)(2)](2) and toluene in the absence of MeCN was found to give [2 + 2] cycloaddition adducts. The structures have been unambiguously determined by X-ray structural analysis. Deuterium labeling experiments were conducted to confirm the mechanism hypothesis.