4b,5,10,10a-tetrahydro-5,10-methanobenz[b]fluoren-11-one | 490039-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 4b,5,10,10a-tetrahydro-5,10-methanobenz[b]fluoren-11-one
• 英文别名: (1S,2R,10S,11R)-pentacyclo[9.6.1.02,10.03,8.012,17]octadeca-3,5,7,12,14,16-hexaen-9-one
• CAS: 490039-67-3
• 化学式: C₁₈H₁₄O
• 分子量: 246.309
• InChiKey: SDGCDFLUGUPAKF-TWMKSMIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,4-二氢-1,4-甲桥萘 、 2-碘苯甲醛 在 dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) 锌 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以75%的产率得到4b,5,10,10a-tetrahydro-5,10-methanobenz[b]fluoren-11-one
  参考文献：
  名称：

  Facile β-Alkyl and β-Hydride Elimination in the Nickel-Catalyzed Annulation of o-Iodophenyl Ketones and Aldehydes with Bicyclic Alkenes

  摘要：

  o-Iodoaryl aldehydes react with bicyclic alkenes in the presence of NiBr2(dppe) and Zn powder in acetonitrile at 80 degrees C undergoing annulation to give polycyclic ketone derivatives. Surprisingly, o-iodoaryl alkyl ketones also react with bicyclic alkenes to form polycyclic ketones with structures the same as those from the corresponding o-iodoaryl aldehydes.

  DOI：

  10.1021/ol061051p

文献信息

• Rhodium(I)-Catalyzed Carbonylative Annulation of Iodobenzenes with Strained Olefins and 4-Octyne in the Presence of Furfural Involving<i>ortho</i>-C-H Bond Cleavage
  作者：Takuma Furusawa、Hiroki Tanimoto、Yasuhiro Nishiyama、Tsumoru Morimoto、Kiyomi Kakiuchi

  DOI：10.1002/adsc.201601056

  日期：2017.1.19

  rhodium(I)‐catalyzed carbonylative annulation of iodobenzenes with strained olefins in the presence of furfural as a carbonyl source, accompanied by ortho‐C–H bond cleavage, is reported. The use of 4‐octyne in place of strained olefins also leads to the formation of the corresponding inden‐9‐one. The timely release of the carbonyl moiety via the rhodium‐catalyzed decarbonylation of furfural plays a decisive

  据报道，在糠醛作为羰基来源存在的情况下，铑（I）催化的碘代苯与应变烯烃的羰基化环化反应，伴随着邻-C-H键断裂。使用4-辛炔代替应变烯烃也会导致相应的茚满9-1的形成。通过铑催化的糠醛脱羰基及时释放羰基在该反应中起决定性作用。
• Rhodium-Catalyzed Annulation Reactions of 2-Cyanophenylboronic Acid with Alkynes and Strained Alkenes
  作者：Tomoya Miura、Masahiro Murakami

  DOI：10.1021/ol051249u

  日期：2005.7.1

  A new [3 + 2] annulation reaction was developed in which 2-cyanophenylboronic acid reacted as a three-carbon component with alkynes or alkenes to afford substituted indenones or indanones. The use of an alkynoate even produced benzotropone, a formal [3 + 2 + 2] adduct. The cyclic skeletons were constructed by intramolecular nucleophilic addition of an intermediate organorhodium(I) species to a cyano group.
• Facile β-Alkyl and β-Hydride Elimination in the Nickel-Catalyzed Annulation of <i>o-</i>Iodophenyl Ketones and Aldehydes with Bicyclic Alkenes
  作者：Paritosh Shukla、Chien Hong Cheng

  DOI：10.1021/ol061051p

  日期：2006.6.1

  o-Iodoaryl aldehydes react with bicyclic alkenes in the presence of NiBr2(dppe) and Zn powder in acetonitrile at 80 degrees C undergoing annulation to give polycyclic ketone derivatives. Surprisingly, o-iodoaryl alkyl ketones also react with bicyclic alkenes to form polycyclic ketones with structures the same as those from the corresponding o-iodoaryl aldehydes.