3',4'-dihydrospiro[cyclohexane-1,2'-(1'H)-naphthalen]-1'-one | 7416-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3',4'-dihydrospiro[cyclohexane-1,2'-(1'H)-naphthalen]-1'-one
• 英文别名: 3',4'-dihydro-spiro[cyclohexane-1,2'-naphthalen]-1'-one；3',4'-Dihydro-spiro[cyclohexan-1,2'-naphthalin]-1'-on；1-Oxo-1,2,3,4-tetrahydro-naphthalin-2-spirocyclohexan；1,2-Benzo-cyclohexenon-3-4-spiro-1'-cyclohexan；2,2-Pentamethylen-tetralon-(1)；Spiro[3,4-dihydronaphthalene-2,1'-cyclohexane]-1-one
• CAS: 7416-01-5
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: CAIYBPDHKCKHQY-UHFFFAOYSA-N

物化性质

• 沸点：
  145 °C(Press: 3 Torr)
• 密度：
  1.07224 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  3',4'-dihydrospiro[cyclohexane-1,2'-(1'H)-naphthalen]-1'-one 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 6,7,8,9,10,11-hexahydro-5H-cyclohepta[a]naphthalene
  参考文献：
  名称：

  Christol et al., Bulletin de la Societe Chimique de France, 1958, p. 248,254

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(o-iodophenyl)ethyl methanesulfonate 在 palladium diacetate 正丁基锂 、 三乙胺 、 二异丙胺 、 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 25.0h， 生成 3',4'-dihydrospiro[cyclohexane-1,2'-(1'H)-naphthalen]-1'-one
  参考文献：
  名称：

  腈的Carpalpallading：通过Pd催化ω-（2-碘芳基）烷腈和相关化合物的环化反应合成苯并酮和环戊烯酮。

  摘要：

  已经开发出一种通过腈的分子内碳弹头化合成2，2-二取代的苯并环酮的有效方法。取代的3-（2-碘芳基）丙烷腈的环化以高收率提供茚满酮。该反应与多种官能团相容。该方法已经扩展到四氢萘酮和环戊烯酮的合成。

  DOI：

  10.1021/jo0262006

文献信息

• Synthetic Morphinans and Hasubanans. Part IV. Total Synthesis of 3,14-Dihydroxyisomorphinans, 3-Methoxy-Δ^8,14-morphinans, and 9α-Hydroxy-3-methoxyhasubanan
  作者：Ivo Monković、Henry Wong、Bernard Belleau、Irwin J. Pachter、Yvon G. Perron

  DOI：10.1139/v75-358

  日期：1975.9.1

  The synthesis of a versatile intermediate 4a-(2-aminoethyl)-l,2,3,4,4a,9-hexahydro-6-methoxyphenanthrene (3a) and its utilization in the synthesis of 9α-hydroxy-3-methoxy-17-methylhasubanan (10), 3,14-dimethoxy-17-methylisomorphinan (9l), various 14-hydroxyisomorphinans (9), and 3-methoxy-Δ^8,14-morphinan (11b) is described. A number of 17-alkyl-3,14-dihydroxyisomorphinans were prepared and tested for narcotic antagonist and analgesic activities in laboratory animals. Some of these new compounds have exhibited significant activities.

  合成了一种多用途中间体4a-(2-氨基乙基)-1,2,3,4,4a,9-六氢-6-甲氧基菲(3a)，并研究了其在9α-羟基-3-甲氧基-17-甲基哈苏班烷(10)、3,14-二甲氧基-17-甲基异吗啡烷(9l)、各种14-羟基异吗啡烷(9)和3-甲氧基-Δ^8,14-吗啡烷(11b)合成中的应用。制备了一系列17-烷基-3,14-二羟基异吗啡烷，并在实验动物中测试了它们的麻醉拮抗和镇痛活性。其中一些新化合物表现出显著的活性。

• Azetidinone compound and process for preparation thereof
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP0597423A2

  公开（公告）日：1994-05-18

  There is disclosed an azetidinone compound of the formula [I]: wherein Ring B is a benzene ring which may have substituent(s), R¹ is a hydroxy-substituted lower alkyl group which may have substituent(s), X is oxygen atom and the like, Y is oxygen atom and the like, and Z is a methylene group which may have substituent(s), which is useful as a synthetic intermediate of the 1β-methylcarbapenem-type antibacterial agent.

  本发明公开了一种式[I]的氮杂环丁酮化合物： 其中环 B 是可能具有取代基的苯环，R¹ 是可能具有取代基的羟基取代的低级烷基，X 是氧原子等，Y 是氧原子等，Z 是可能具有取代基的亚甲基，该化合物可用作 1β-甲基碳青霉烯类抗菌剂的合成中间体。
• Synthesis and pharmacological evaluation of 4a-phenanthrenamine derivatives acting at the phencyclidine binding site of the N-methyl-D-aspartate receptor complex
  作者：Christopher F. Bigge、Thomas C. Malone、Sheryl J. Hays、Graham Johnson、Perry M. Novak、Leonard J. Lescosky、Daniel M. Retz、Daniel F. Ortwine、Albert W. Probert

  DOI：10.1021/jm00066a007

  日期：1993.7

  A novel series of octahydrophenanthrenamines and their heterocyclic analogues have been synthesized as potential noncompetitive antagonists of the N-methyl-D-aspartate (NMDA) receptor complex. The compounds were evaluated for their affinity at the phencyclidine (PCP) binding site by determining their ability to displace [H-3]TCP from crude rat brain synaptic membranes. A wide range of affinities were observed, with the most potent analogs possessing IC50's equivalent to that of the reference agent MK-801 (3,dizocilpine). NMDA antagonist activity was demonstrated by prevention of glutamate-induced accumulation of [Ca-45(2+)] in cultured rat cortical neurons. Selected compounds were also studied in vivo to determine their ability to prevent the lethal effects of systemically injected NMDA in the mouse. In general, the SAR of the phenanthrenamine series may be summarized as follows: (a) for the amino group at C4a, NHMe > NH2 > NHEt much-greater-than NC5H10; (b) for the B-ring substitution, X = CH2 > S > 0; (c) unsaturation of the C ring decreases receptor affinity; (d) cis-ring fusion between the B and C rings is desirable; (e) 6-hydroxy or 6-methoxy substitution of the phenanthrenamine system identified an additional hydrogen bonding interaction that substantially increased receptor affinity; (f) spiro analogues (such as 55, IC50 = 3400 nM), which altered the point of attachment of the C ring, caused a substantial reduction in PCP-site affinity. Molecules from this series were useful for refining a pharmacophore model consistent with previous models of the PCP site. In this model, the (R)-(+)-phenanthrenamine 13 superimposes closely onto MK-801 (3), and the angular 4a-amino group is believed to hydrogen bond with a putative receptor site atom. In the phenanthrenamine and thiaphenanthrenamine series, the (R)-(+)-enantiomers (9, 13, and 44) are more potent by approximately 5-10-fold than their corresponding (S)-(-)-enantiomers with respect to their affinity for the PCP site, their ability to prevent accumulation of [Ca-45(2+)] in cultured neuronal cells, and their protection against the lethal effects of NMDA in mice. In general, there was no separation between the dose that prevented NMDA lethality and the dose that produced ataxia in mice, except in the case of the thiaphenanthrenamines 41 and 43. We have not yet obtained evidence that this small separation in activity offers a therapeutic advantage in the treatment of cerebral ischemia or other neurodegenerative disorders.
• Mousseron et al., Bulletin de la Societe Chimique de France, 1957, p. 346,352
  作者：Mousseron et al.

  DOI：——

  日期：——
• Sen-Gupta, Journal of the Indian Chemical Society, 1942, vol. 19, p. 467,471
  作者：Sen-Gupta

  DOI：——

  日期：——