(-)-(4aR,8aS)-octahydro-2(1H)-naphthalenone | 91684-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(4aR,8aS)-octahydro-2(1H)-naphthalenone
• 英文别名: (4aR)-(4ar,8ac)-octahydro-naphthalen-2-one；3,4,4aβ,5,6,7,8,8aβ-Octahydronaphthalin-2(1H)-on；cis-Bicyclo<4.4.0>decanon-2；cis-<2>Decalon；cis-Decalin-2-on；cis-2-Decalon；2(1H)-Naphthalenone, octahydro-, (4aR,8aS)-rel-；(4aR,8aS)-3,4,4a,5,6,7,8,8a-octahydro-1H-naphthalen-2-one
• CAS: 91684-30-9
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: LGVJRKCQQHOWAU-BDAKNGLRSA-N

物化性质

• 沸点：
  255.0±0.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (-)-(4aR,8aS)-octahydro-2(1H)-naphthalenone 、 乙酸异丙烯酯 以0%的产率得到
  参考文献：
  名称：

  Thompson Hugh W., Gaglani Kamlesh D., J. Chem. Soc. PerKin Trans. 2, (1993) N 5, S 967-972

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S,4aR,8aS)-decahydro-2-naphthol 以91%的产率得到
  参考文献：
  名称：

  Thompson Hugh W., Gaglani Kamlesh D., J. Chem. Soc. PerKin Trans. 2, (1993) N 5, S 967-972

  摘要：

  DOI：

文献信息

• The Iron(II) Complex [Fe(CF₃SO₃)₂(mcp)] as a Convenient, Readily Available Catalyst for the Selective Oxidation of Methylenic Sites in Alkanes
  作者：Mercè Canta、David Font、Laura Gómez、Xavi Ribas、Miquel Costas

  DOI：10.1002/adsc.201300923

  日期：2014.3.10

  The efficient and selective oxidation of secondary CH sites of alkanes is achieved by using low catalyst loadings of a non‐expensive, readily available iron catalyst [Fe(II)(CF3SO3)2(mcp)], Fe‐mcp, [mcp=N,N′‐dimethyl‐N,N′‐bis(2‐pyridylmethyl)cyclohexane‐trans‐1,2‐diamine]}, and hydrogen peroxide (H2O2) as oxidant, via a simple reaction protocol. Natural products are selectively oxidized and isolated

  次级C的有效和选择性氧化烷烃h的位点是通过使用非昂贵的，容易得到的铁催化剂的低催化剂负载的[Fe（II）（CF实现3 SO 3）2（MCP）]， Fe的MCP，[MCP = ñ，N'-二甲基- ñ，N' -双（2-吡啶基甲基）环己烷TRAN S--1,2-二胺]}，和过氧化氢（H 2 ö 2）作为氧化剂，通过一个简单的反应方案。天然产物被选择性地氧化并以合成上可接受的产率分离。容易获得大量催化剂和CH氧化过程的简便性使得该系统成为在制备规模上以较短的反应时间进行烷烃CH氧化反应的特别方便的工具。
• DI-OR TRIAZA-SPIRO [4,5] DECANE DERIVATIVES
  申请人：——

  公开号：US20030176701A1

  公开（公告）日：2003-09-18

  The present invention relates to compounds of the general formula 1 wherein R 1 is C 6-10 -cycloalkyl, optionally substituted by lower alkyl or —C(O)O-lower alkyl; decahydro-naphthalen-1-yl; decahydro-naphthalen-2-yl; indan-1-yl or indan-2-yl, optionally substituted by lower alkyl; decahydro-azulen-2-yl; bicyclo[6.2.0]dec-9-yl; acenaphthen-1-yl; 2,3-dihydro-1H-phenalen-1-yl; 2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl or octahydro-inden-2-yl; R 2 is hydrogen; lower alkyl; ═O or phenyl, optionally substituted by lower alkyl, halogen or alkoxy; 2 is cyclohexyl or phenyl, optionally substituted by lower alkyl, halogen or alkoxy; X is —CH(OH)—; —C(O)—; —CHR 3 —; —CR 3 ═; —O—; —S—; —CH(COOR 4 )— or —C(COOR 4 )═; Y is —CH 2 —; —CH═; —CH(COOR 4 )—, —C(COOR 4 )═; or —C(CN)—; R 3 is hydrogen or lower alkoxy; R 4 is lower alkyl, cycloalkyl, phenyl, or benzyl and either a or b is optionally an additional bond, and to pharmaceutically acceptable acid addition salts thereof. The compounds are agonists of the orphanin FQ (QFQ) receptor and therefore useful in the treatment of diseases, related to this receptor.

  本发明涉及一般式1的化合物， 其中， R1是C6-10环烷基，可选地被较低烷基或-C（O）O-较低烷基取代； 十氢萘-1-基；十氢萘-2-基；吲哚-1-基或吲哚-2-基，可选地被较低烷基取代； 十氢-萜烯-2-基； 双环[6.2.0]癸-9-基； 萘并环[1]苯-1-基； 2,3-二氢-1H-菲-1-基； 2,3,3a,4,5,6-六氢-1H-菲-1-基或八氢-茚-2-基； R2是氢；较低烷基；═O或苯基，可选地被较低烷基，卤素或烷氧基取代； 2是环己基或苯基，可选地被较低烷基，卤素或烷氧基取代； X是—CH（OH）—；—C（O）—；—CHR3—；—CR3═；—O—；—S—；—CH（COOR4）—或—C（COOR4）═； Y是—CH2—；—CH═；—CH（COOR4）—，—C（COOR4）═；或—C（CN）—； R3是氢或较低烷氧基； R4是较低烷基，环烷基，苯基或苯甲基； a或b是可选的额外键，以及其药学上可接受的酸盐。 这些化合物是孤儿受体FQ（QFQ）激动剂，因此在与该受体相关的疾病的治疗中有用。
• 1,3,8-Triaza-spiro 4,5 decan-4-on derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0921125A1

  公开（公告）日：1999-06-09

  The present invention relates to compounds of the general formula wherein R1is hydrogen, lower alkyl, halogen, lower alkoxy, trifluoromethyl, lower alkyl-phenyl or (C5-7)-cycloalkyl; R2is hydrogen, lower alkyl, phenyl or lower alkyl-phenyl; R3is hydrogen, lower alkyl, benzyl, lower alkyl-phenyl, lower alkyl-diphenyl, triazinyl, cyanomethyl, lower alkyl-piperidinyl, lower alkyl-naphthyl, (C5-7)-cycloalkyl, lower alkyl-(C5-7)-cycloalkyl, lower alkyl-pyridinyl, lower alkyl-morpholinyl, lower alkyl-dioxolanyl, lower alkyl-oxazolyl or lower alkyl-2-oxo-oxazolidinyl and wherein the ring systems may be substituted by additional lower alkyl, lower alkoxy, trifluoromethyl or phenyl, or -(CH2)nC(O)O-lower alkyl, -(CH2)nC(O)NH2, -(CH2)nC(O)N(lower alkyl)2, -(CH2)nOH or -(CH2)nC(O)NHCH2C6H5; R4is hydrogen, lower alkyl or nitrilo; Ais a ring system, consisting of (a) (C5-15)-cycloalkyl, which may be in addition to R4optionally substituted by lower alkyl, trifluoromethyl, phenyl, (C5-7)-cycloalkyl, spiro-undecan-alkyl or by 2-norbornyl, or is one of the following groups dodecahydro-acenaphthylen-1yl (e), bicyclo[6.2.0]dec-9-yl (f) and bicyclononan-9-yl (g); and wherein R5 and R6are hydrogen, lower alkyl or taken together and with the carbon atoms to which they are attached form a phenyl ring; R7is hydrogen or lower alkyl; the dotted line represents an optional bond and nis 1 to 4; and to pharmaceutically acceptable acid addition salts thereof. Compounds of the present invention are agonists and/or antagonists of the Orphanin FQ (OFQ) receptor. Consequently they will be useful in the treatment of memory and attention deficits, psychiatric, neurological and physiological disorders, especially, but not limited to, amelioration of symptoms of anxiety and stress disorders, depression, trauma, memory loss due to Alzheimer's disease or other dementias, epilepsy and convulsions, acute and/or chronic pain conditions, symptoms of addictive drug withdrawal, control of water balance, Na+ excretion, arterial blood pressure disorders and metabolic disorders such as obesity.

  本发明涉及通式如下的化合物 式中 R1是氢、低级烷基、卤素、低级烷氧基、三氟甲基、低级烷基苯基或(C5-7)-环烷基； R2 是氢、低级烷基、苯基或低级烷基苯基； R3是氢、低级烷基、苄基、低级烷基-苯基、低级烷基-二苯基、三嗪基、氰甲基、低级烷基-哌啶基、低级烷基-萘基、（C5-7）-环烷基、低级烷基-（C5-7）-环烷基、低级烷基-吡啶基、低级烷基-吗啉基、低级烷基-二氧戊环基、低级烷基-噁唑基或低级烷基-2-氧代-噁唑烷基，其中环系统可被额外的低级烷基、低级烷氧基、三氟甲基或苯基取代，或被-(CH2)nC(O)O-低级烷基、-(CH2)nC(O)NH2、-(CH2)nC(O)N(低级烷基)2、-(CH2)nOH 或 -(CH2)nC(O)NHCH2C6H5取代； R4 是氢、低级烷基或硝基； A 是一个环状系统，包括 (a) (C5-15)-环烷基，除 R4 外，还可被低级烷基、三氟甲基、苯基、(C5-7)-环 烷基、螺十一烷基或 2-降冰片基取代，或为以下基团之一 十二氢-苊烯-1-基 (e)、双环[6.2.0]癸-9-基 (f) 和双环壬-9-基 (g)； 其中 R5 和 R6 为氢、低级烷基或与它们所连接的碳原子一起形成苯环； R7 为氢或低级烷基； 虚线代表任选键，且 n为 1 至 4； 及其药学上可接受的酸加成盐。 本发明的化合物是孤儿素 FQ（OFQ）受体的激动剂和/或拮抗剂。因此，它们可用于治疗记忆和注意力缺陷、精神、神经和生理疾病，特别是但不限于改善焦虑和应激障碍、抑郁症、创伤、阿尔茨海默病或其他痴呆症引起的记忆丧失、癫痫和抽搐、急性和/或慢性疼痛、成瘾药物戒断症状、控制水平衡、Na+排泄、动脉血压紊乱和代谢紊乱（如肥胖）等症状。
• Di-or triaza-spiro(4,5)decane derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0963985A2

  公开（公告）日：1999-12-15

  The present invention relates to compounds of the general formula wherein R1is C6-10-cycloalkyl, optionally substituted by lower alkyl or -C(O)O-lower alkyl; decahydro-naphthalen-1-yl; decahydro-naphthalen-2-yl; indan-1-yl or indan-2-yl, optionally substituted by lower alkyl; decahydro-azulen-2-yl; bicyclo[6.2.0]dec-9-yl; acenaphthen-1-yl; 2,3-dihydro-1H-phenalen-1-yl; 2,3,3a,4,5,6-hexahydro-1H-phenalen-1-yl or octahydro-inden-2-yl; R2is hydrogen; lower alkyl; =O or phenyl, optionally substituted by lower alkyl, halogen or alkoxy; Ⓐis cyclohexyl or phenyl, optionally substituted by lower alkyl, halogen or alkoxy; Xis -CH(OH)-; -C(O)-; -CHR3-; -CR3=; -O-; -S-; -CH(COOR4)- or - C(COOR4)=; Yis -CH2-; -CH=; -CH(COOR4)-, -C(COOR4)=; or -C(CN)-; R3is hydrogen or lower alkoxy; R4is lower alkyl, cycloalkyl, phenyl, or benzyl and either a or b is optionally an additional bond, and to pharmaceutically acceptable acid addition salts thereof. The compounds are agonists and/or antagonists of the orphanin FQ (QFQ) receptor and therefore useful in the treatment of diseases, related to this receptor.

  本发明涉及通式如下的化合物 式中 R1为C6-10-环烷基，任选被低级烷基或-C(O)O-低级烷基取代；十氢萘-1-基；十氢萘-2-基；茚-1-基或茚-2-基，任选被低级烷基取代；十氢氮杂环烯-2-基；双环[6.2.0]癸-9-基；苊-1-基；2,3-二氢-1H-苯戊烯-1-基；2,3,3a,4,5,6-六氢-1H-苯戊烯-1-基或八氢-茚-2-基； R2是氢；低级烷基；=O或苯基，可选择被低级烷基、卤素或烷氧基取代； 是环己基或苯基，可选择被低级烷基、卤素或烷氧基取代； X是-CH(OH)-；-C(O)-；-CHR3-；-CR3=；-O-；-S-；-CH(COOR4)-或-C(COOR4)=； Y是-CH2-；-CH=；-CH(COOR4)-，-C(COOR4)=；或-C(CN)-； R3 是氢或低级烷氧基； R4 是低级烷基、环烷基、苯基或苄基 和 a 或 b 是可选的附加键、 及其药学上可接受的酸加成盐。 这些化合物是孤儿素 FQ（QFQ）受体的激动剂和/或拮抗剂，因此可用于治疗与该受体有关的疾病。
• Regioselective Oxidation of Nonactivated Alkyl C–H Groups Using Highly Structured Non-Heme Iron Catalysts
  作者：Laura Gómez、Mercè Canta、David Font、Irene Prat、Xavi Ribas、Miquel Costas

  DOI：10.1021/jo302196q

  日期：2013.2.15

  Selective oxidation of alkyl C-H groups constitutes one of the highest challenges in organic synthesis. In this work, we show that mononuclear iron coordination complexes Lambda-[Fe(CF3SO3)(2)((S,S,R)-MCPP)] (Lambda-1P), Delta-[Fe(CF3SO3)(2)((R,R,R)-MCPP)] (Delta-1P), Lambda-[Fe(CF3SO3)(2)((S,S,R)-BPBPP)] (Lambda-2P), and Delta-[Fe(CF3SO3)(2)((R,R,R)-BPBPP)] (Delta-2P) catalyze the fast, efficient, and selective oxidation of nonactivated alkyl C-H groups employing H2O2 as terminal oxidant. These complexes are based on tetradentate N-based ligands and contain iron centers embedded in highly structured coordination sites defined by two bulky 4,5-pinenopyridine donor ligands, a chiral diamine ligand backbone, and chirality at the metal (Lambda or Delta). X-ray diffraction analysis shows that in Lambda-1P and Lambda-2P the pinene rings create cavity-like structures that isolate the iron site. The efficiency and regioselectivity in catalytic C-H oxidation reactions of these structurally rich complexes has been compared with those of Lambda-[Fe(CF3SO3)(2)((S,S)-MCP)] (Lambda-1), Lambda-[Fe(CF3SO3)(2)((S,S)-BPBP)] (Lambda-2), Delta-[Fe(CF3SO3)(2)((R,R)-BPBP)] (Delta-2), Lambda-[Fe(CH3CN)(2)((S,S)-BPBP)] (SbF6)(2) (Lambda-2SbF(6)), and Delta-[Fe(CH3CN)(2)((R,R)-BPBP)](SbF6)(2) (Delta-2SbF(6)), which lack the steric bulk introduced by the pinene rings. Cavity-containing complexes Lambda-1P and Lambda-2P exhibit enhanced activity in comparison with Delta-1P, Delta-2P, Lambda-1, Lambda-2, and Lambda-2SbF(6). The regioselectivity exhibited by catalysts Lambda-1P, Lambda-2P, Delta-1P, and Delta-2P in the C-H oxidation of simple organic molecules can be predicted on the basis of the innate properties of the distinct C-H groups of the substrate. However, in specific complex organic molecules where oxidation of multiple C-H sites is competitive, the highly elaborate structure of the catalysts allows modulation of C-H regioselectivity between the oxidation of tertiary and secondary C-H groups and also among multiple methylene sites, providing oxidation products in synthetically valuable yields. These selectivities complement those accomplished with structurally simpler oxidants, including non-heme iron catalysts Lambda-2 and Lambda-2SbF(6).

表征谱图