(1aα,7aα)-1a,2,7,7a-Tetrahydro-1H-cyclopropanaphthalen-2-one | 27346-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1aα,7aα)-1a,2,7,7a-Tetrahydro-1H-cyclopropanaphthalen-2-one
• 英文别名: (+/-)-1,1a,7,7a-tetrahydro-cyclopropa[b]naphthalen-2-one；(+/-)-1,1a,7,7a-Tetrahydro-cyclopropa[b]naphthalin-2-on；(1aS,7aS)-1,1a,7,7a-tetrahydrocyclopropa[b]naphthalen-2-one
• CAS: 27346-16-3
• 化学式: C₁₁H₁₀O
• 分子量: 158.2
• InChiKey: WMMQEAXDGPIZJS-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1aα,7aα)-1a,2,7,7a-Tetrahydro-1H-cyclopropanaphthalen-2-one 在 sodium tetrahydroborate 、 水 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 0.75h， 生成 (1aα,2β,7aα)-1a,2,7,7a-Tetrahydro-1H-cyclopropanaphthalen-2-ol
  参考文献：
  名称：

  Proton-carbon-13 coupling constants in carbocations. 6. Generation and trapping of the (1a.alpha.,7a.alpha.)-1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalen-2-yl cation

  摘要：

  New synthetic routes to (1a-alpha,2-beta,7b-alpha)-1a,2,3,7b-tetrahydro-1H-cyclopropa[alpha]naphthalen-2-ol (4b) and (1a-alpha,2-alpha,7a-alpha)-1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalen-2-ol (6b) have been established involving dichlorocarbene addition to the appropriate dihydronaphthalene as the key step. Ionization of either alcohol 4b or 6b in FSO3H/SO2CIF at - 130-degrees-C produces the title cation 5b, in which the positive charge is stabilized by the adjacent benzo and cyclopropyl moieties. This is the same cation as that obtained previously by protonation of 1,6-methanol[10]annulene (1). Generation of the cation 5b by protonation of C11-C-13-enriched 1 has shown that the C11 bridge methylene carbon is incorporated into both benzylic positions (C2 and C7) and not the apical cyclopropyl carbon (C1). Application of the DELTA-J equation shows that 5b adopts an anti-boat conformation in this superacid medium.

  DOI：

  10.1021/jo00006a015
• 作为产物：
  描述：

  (1aα,2α,7aα)-1a,2,7,7a-Tetrahydro-1H-cyclopropanaphthalen-2-ol 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以66%的产率得到(1aα,7aα)-1a,2,7,7a-Tetrahydro-1H-cyclopropanaphthalen-2-one
  参考文献：
  名称：

  Proton-carbon-13 coupling constants in carbocations. 6. Generation and trapping of the (1a.alpha.,7a.alpha.)-1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalen-2-yl cation

  摘要：

  New synthetic routes to (1a-alpha,2-beta,7b-alpha)-1a,2,3,7b-tetrahydro-1H-cyclopropa[alpha]naphthalen-2-ol (4b) and (1a-alpha,2-alpha,7a-alpha)-1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalen-2-ol (6b) have been established involving dichlorocarbene addition to the appropriate dihydronaphthalene as the key step. Ionization of either alcohol 4b or 6b in FSO3H/SO2CIF at - 130-degrees-C produces the title cation 5b, in which the positive charge is stabilized by the adjacent benzo and cyclopropyl moieties. This is the same cation as that obtained previously by protonation of 1,6-methanol[10]annulene (1). Generation of the cation 5b by protonation of C11-C-13-enriched 1 has shown that the C11 bridge methylene carbon is incorporated into both benzylic positions (C2 and C7) and not the apical cyclopropyl carbon (C1). Application of the DELTA-J equation shows that 5b adopts an anti-boat conformation in this superacid medium.

  DOI：

  10.1021/jo00006a015

文献信息

• 516. Tropolones. Part IX. 2 : 3-Dihydro-2 : 3-methylene-1 : 4-naphthaquinone
  作者：G. L. Buchanan、J. K. Sutherland

  DOI：10.1039/jr9560002620

  日期：——
• Julia et al., Bulletin de la Societe Chimique de France, 1959, p. 1449,1452
  作者：Julia et al.

  DOI：——

  日期：——
• Mechanism of the Carvone Hydrobromide → Eucarvone Transformation
  作者：Eugene E. van Tamelen、John McNary、Frank A. Lornitzo

  DOI：10.1021/ja01562a052

  日期：1957.3
• Julia; Bonnet, Bulletin de la Societe Chimique de France, 1957, p. 1340,1344
  作者：Julia、Bonnet

  DOI：——

  日期：——
• [EN] COMPOUNDS FOR THE TREATMENT OF INFLAMMATORY DISORDERS<br/>[FR] COMPOSÉS POUR TRAITER DES TROUBLES INFLAMMATOIRES
  申请人：SCHERING CORP

  公开号：WO2010036638A2

  公开（公告）日：2010-04-01

  This invention relates to compounds of the Formula (I) as described herein, or a pharmaceutically acceptable salt, solvate or ester thereof, which can be useful for the treatment of diseases or conditions mediated by MMPs, ADAMs, TACE, aggrecanase, TNF- or combinations thereof.