1-(6,7-dihydro-5H-benzocycohepten-9-yl)pyrrolidine | 25579-44-6

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1-(6,7-dihydro-5H-benzocycohepten-9-yl)pyrrolidine
• 英文别名: 5H-6,7-dihydro-9-(1-pyrrolidinyl)benzocycloheptene；1-(8,9-dihydro-7H-benzocyclohepten-5-yl)-pyrrolidine；1-(8,9-dihydro-7H-benzo[7]annulen-5-yl)pyrrolidine
• CAS: 25579-44-6
• 化学式: C₁₅H₁₉N
• 分子量: 213.323
• InChiKey: SJYLFJVYBMZKIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  370.3±22.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(6,7-dihydro-5H-benzocycohepten-9-yl)pyrrolidine 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 N,N-diphenyl-[(R)-1,1'-spirobiindane-7,7'-diyl]-phosphoramidite 、 氢气 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以96%的产率得到(-)-1-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-yl)pyrrolidine
  参考文献：
  名称：

  手性螺N，N-二芳基亚磷酰胺的铱配合物催化未官能化烯胺的不对称加氢

  摘要：

  合成了手性螺，N，N-二芳基亚磷酰胺。这些新的手性螺单磷酰胺盐是有效的配体，用于铱催化衍生自简单烷基芳基酮的未官能化烯胺的不对称加氢，从而提供了具有良好对映选择性（高达90％ee）的手性叔胺。

  DOI：

  10.1002/cjoc.201090293
• 作为产物：
  描述：

  四氢吡咯 、 1-苯并环庚酮 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 1-(6,7-dihydro-5H-benzocycohepten-9-yl)pyrrolidine
  参考文献：
  名称：

  鉴定一系列新型的选择性5-HT7受体拮抗剂。

  摘要：

  从高通量筛选中鉴定出含有苯并环庚酮核心的新型5-HT（7）受体拮抗剂。分子建模和SAR研究已将这些难处理的命中转化为更有效，更具选择性和更易处理的序列，例如化合物（25）SB-691673。

  DOI：

  10.1016/s0960-894x(03)00077-5

文献信息

• REACTIONS OF CYCLIC ENAMINES WITH DICYANOMETHYLENECYCLOPROPENES. FORMATION OF MEDIUM RING COMPOUNDS AND TRANSANNULATION TO FULVENES
  作者：Otohiko Tsuge、Shigeru Okita、Michihiko Noguchi、Shuji Kanemasa

  DOI：10.1246/cl.1982.847

  日期：1982.6.5

  Several cyclic enamines with five to seven-membered rings react with 2-(1,2-diphenyl-3-cyclopropenylidene)propanedinitrile to give medium ring compounds, showing that the latter is a versatile reagent which can insert three carbon atoms between α- and β-carbons of cyclic enamines. These medium ring compounds undergo transannular reactions on treatment with hydrochloric acid to yield fulvene derivatives with

  几种具有五至七元环的环状烯胺与 2-(1,2-diphenyl-3-cyclopropenylidene)propanedinitrile 反应生成中等环化合物，表明后者是一种通用试剂，可以在 α- 和环状烯胺的β-碳。这些中环化合物在用盐酸处理时发生环间反应，生成富烯衍生物，并消除了烯胺中的胺组分。
• Reactions of enamines with trifluoroacetic anhydride: trifluoroacetylation and the formation of 1,3-oxazines
  作者：Willem Verboom、David N. Reinhoudt、Sybolt Harkema、Gerrit J. Van Hummel

  DOI：10.1021/jo00138a033

  日期：1982.8
• Synthesis, Stability, and Spectroscopic and Electronic Properties of Three Benzocyclohepta[<i>a</i>]azulenylium Ions¹
  作者：Kazuo Yamane、Hiroyuki Yamamoto、Makoto Nitta

  DOI：10.1021/jo020136a

  日期：2002.11.1

  Novel pi-systems, three benzocyclohepta[a]azulenylium ions, 7a-c, are synthesized, and their stability and properties have been characterized in terms of the position of the benzo-annulation and compared with those of the parent cyclohepta[a]azulenylium ion 4. Benzocyclohepta[6,7-a]azulenylium ion (7a) (pK(R+) = 7.3,E-red = -0.567 V vs Ag/Ag+) and benzocyclohepta[6,5-a]azulenylium ion (7b) ( pK(R+) = 5.1, E-red = - 0.482 V vs Ag/Ag+), which are annulated with benzene on the position having a high bond order of 4, are not appreciably destabilized compared with cyclohepta[a]azulenylium ion (4) (pK(R+) = 7.3, E-red = -0.458 V vs Ag/Ag+). On the other hand, benzocyclohepta[7,6-a]azulenylium ion (7c) (pK(R+) = 1.6, E-red = -0.197 V vs Ag/Ag+) is considerably destabilized, probably due to enhanced contribution of the quinoid structure of the benzene ring, which is annulated on the position having a low bond order of the cyclohepta[a]azulenylium ion moiety. Furthermore, the cations 7a and 7b are more stable than 12,13-dihydrobenzocyclohepta[7,6-a]azulenylium ion (25) (pK(R+) = 4.8, E-red = -0.513 V vs Ag/Ag+), which is a dihydrogenated compound of 7a, while 7c is less stable than 25. These features are reflected in the considerable red shift of the longest absorption maximum of the electronic spectrum of 7c, as compared with those of 4, 7a, and 7b, and in the chemical shifts of the protons and their coupling constants of the H-1 NMR spectra. Furthermore, the H-1 NMR spectra and electronic spectra of 5H-benzocyclohepta[6,7-a]azulen-5-one (8a) and 7H-benzocyclohepta[6,5-a]azulen-7-one (8b) in acidic media have also been studied to clarify the spectral characteristics similar to those of 7a and 7b.
• TSUGE, OTOHIKO;OKITA, SHIGERU;NOGUCHI, MICHIHIKO;KANEMASA, SHUJI, CHEM. LETT., 1982, N 6, 847-850
  作者：TSUGE, OTOHIKO、OKITA, SHIGERU、NOGUCHI, MICHIHIKO、KANEMASA, SHUJI

  DOI：——

  日期：——
• VERBOOM, W.;REINHOUDT, D. N.;HARKEMA, S.;VAN, HUMMEL, G. J., J. ORG. CHEM., 1982, 47, N 17, 3339-3342
  作者：VERBOOM, W.、REINHOUDT, D. N.、HARKEMA, S.、VAN, HUMMEL, G. J.

  DOI：——

  日期：——