9,10-dihydro-9,10-methanoanthracene-9-carboxaldehyde | 60070-19-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-dihydro-9,10-methanoanthracene-9-carboxaldehyde
• 英文别名: 9-formyl-9,10-dihydro-9,10-methanoanthracene；9-Formyl-9,10-dihydro-9,10-methanoanthracen；tetracyclo[6.6.1.02,7.09,14]pentadeca-2,4,6,9,11,13-hexaene-1-carbaldehyde
• CAS: 60070-19-1
• 化学式: C₁₆H₁₂O
• 分子量: 220.271
• InChiKey: ZAELYRWEXINIKF-UHFFFAOYSA-N

物化性质

• 熔点：
  102.5 °C
• 沸点：
  351.6±31.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  9,10-dihydro-9,10-methanoanthracene-9-carboxaldehyde 在 chromium(VI) oxide 、 sodium hydroxide 、 硫酸 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 2-(1-Tetracyclo[6.6.1.02,7.09,14]pentadeca-2,4,6,9,11,13-hexaenyl)acetic acid
  参考文献：
  名称：

  Dibenzotetracyclic derivatives. II. Synthesis of 9-aminoalkyl-9,10-dihydro-9,10-methanoanthracenes.

  摘要：

  报告了 9-氨基烷基-9，10-二氢-9，10-甲桥蒽 (2) 的合成。关键的中间体 9-甲酰基-9，10-二氢-9，10-甲桥蒽 (4) 是由 9-氨基-12-羟基-9，10-二氢-9，10-乙桥蒽 (3b) 通过亚硝酸脱氨合成的。氨基醇 (3b) 由蒽-9-甲醛开始，分 5 步合成。

  DOI：

  10.1248/cpb.27.1806
• 作为产物：
  描述：

  12-Acetoxy-9,10-dihydro-9,10-ethanoanthracen-9-carbaldehyde 在 chromium(VI) oxide 、 硫酸 、 sodium nitrite 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 生成 9,10-dihydro-9,10-methanoanthracene-9-carboxaldehyde
  参考文献：
  名称：

  Dibenzotetracyclic derivatives. II. Synthesis of 9-aminoalkyl-9,10-dihydro-9,10-methanoanthracenes.

  摘要：

  报告了 9-氨基烷基-9，10-二氢-9，10-甲桥蒽 (2) 的合成。关键的中间体 9-甲酰基-9，10-二氢-9，10-甲桥蒽 (4) 是由 9-氨基-12-羟基-9，10-二氢-9，10-乙桥蒽 (3b) 通过亚硝酸脱氨合成的。氨基醇 (3b) 由蒽-9-甲醛开始，分 5 步合成。

  DOI：

  10.1248/cpb.27.1806

文献信息

• Methanoanthraceneyl methyl piperidinyl compounds
  申请人：Zeneca Limited

  公开号：US05512575A1

  公开（公告）日：1996-04-30

  Compounds of formula I or I', ##STR1## wherein X and Y are independently selected from hydrogen, halo, and (1-6C)alkoxy; R.sup.1 is selected from (A) (1-6C)alkyl; (B) phenyl and naphthyl or substituted versions thereof; (C) phenyl (1-3C)alkyl and naphthyl (1-3C) alkyl; (D) five- and six-membered heteroaryl rings; (E) heteroaryl (1-3C)alkyl and pharmaceutically acceptable salts thereof, useful in the treatment of neuropsychiatric disorders such as psychoses; pharmaceutical compositions comprising a compound of formula I or I' and a pharmaceutically acceptable diluent or carrier; and methods of treating neuropsychiatric disorders comprising administering to a mammal (including man) in need of such treatment an effective amount of a compound of formula I or I', or a pharmaceutically acceptable salt thereof are claimed. The invention also relates to novel processes for producing enantiomeric methanoanthracenyl sulfoxides.

  化学式I或I'的化合物，其中X和Y分别选自氢、卤素和(1-6C)烷氧基；R.sup.1选自(A)(1-6C)烷基；(B)苯基和萘基或其取代物；(C)苯基(1-3C)烷基和萘基(1-3C)烷基；(D)五元和六元杂芳环；(E)杂芳基(1-3C)烷基及其药学上可接受的盐，用于治疗精神病等神经精神障碍；包括化合物I或I'和药学上可接受的稀释剂或载体的药物组合物；以及治疗神经精神障碍的方法，包括向需要此类治疗的哺乳动物(包括人类)施用化合物I或I'或其药学上可接受的盐的有效量。该发明还涉及用于生产对映体甲基蒽基亚砜的新工艺。
• [EN] MCHIR ANTAGONISTS<br/>[FR] ANTAGONISTES DU MCH1R
  申请人：ASTRAZENECA AB

  公开号：WO2004004726A1

  公开（公告）日：2004-01-15

  The present invention provides compounds of formula (I), wherein R1 represents a C1-4alkoxy group optionally substituted by one or more fluoro or a C1-4alkyl group optionally substituted by one or more fluoro; n represents 0 or 1; R2 represents a C1-4alkyl group optionally substituted by one or more fluoro or a C1-4alkoxy group optionally substituted by one or more fluoro; m represents 0 or 1; R3 represents H or a C1-4alkyl group; L1 represents an alkylene chain (CH2)r in which r represents 2 or 3 or L1 represents a cyclohexyl group wherein the two nitrogens bearing R3 and R4, respectively, are linked to the cyclohexyl group either via the 1,3 or the 1,4 positions of the cyclohexyl group or L1 represents a cyclopentyl group wherein the two nitrogens bearing R3 and R4, respectively, are linked to the cyclopentyl group via the 1,3 position of the cyclopentyl group and additionally when R5 represents 9, 10-methanoanthracen-9(10H)-yl the group -L1-N(R4)- together represents a piperidyl ring which is linked to L2 through the piperidinyl nitrogen and to N-R3 via the 4 position of the piperidyl ring with the proviso that when R5 represents 9, 10-methanoanthracen-9(10H)-yl then r is only 2; R4 represents H or a C1-4alkyl group optionally substituted by one or more of the following: an aryl group or a heteroaryl group; L2 represents a bond or an alkylene chain (CH2)s in which s represents 1, 2 or 3 wherein the alkylene chain is optionally substituted by one or more of the following: a C1-4alkyl group, phenyl or heteroaryl; R5 represents aryl, a heterocyclic group or a C3-8cycloalkyl group which is optionally fused to a phenyl or to a heteroaryl group; as well as optical isomers and racemates thereof as well as pharmaceutically acceptable salts, thereof; with provisos, processes for preparing such compounds, their use in the treatment of obesity, psychiatric disorders, cognitive disorders, memory disorders, schizophrenia, epilepsy, and related conditions, and neurological disorders such as dementia, multiple sclerosis, Parkinson's disease, Huntington's chorea and Alzheier's disease and pain related disorders and to pharmaceutical compositions containing them.

  本发明提供了以下式（I）的化合物，其中R1代表一个C1-4烷氧基团，该基团可以选择地被一个或多个氟或一个C1-4烷基基团选择性地取代；n代表0或1；R2代表一个C1-4烷基基团，该基团可以选择地被一个或多个氟或一个C1-4烷氧基团选择性地取代；m代表0或1；R3代表H或一个C1-4烷基基团；L1代表一个烷基链（CH2）r，其中r代表2或3，或者L1代表一个环己基团，其中分别带有R3和R4的两个氮原子通过环己基团的1,3位或1,4位连接到环己基团，或者L1代表一个环戊基团，其中分别带有R3和R4的两个氮原子通过环戊基团的1,3位连接到环戊基团，另外当R5代表9,10-甲基蒽-9(10H)-基时，-L1-N(R4)-群共同代表一个通过哌啶环与L2通过哌啶氮连接并通过哌啶环的4位与N-R3连接的哌啶环，但当R5代表9,10-甲基蒽-9(10H)-基时，r仅为2；R4代表H或一个C1-4烷基基团，该基团可以选择地被以下之一或多个取代：芳基或杂芳基；L2代表一个键或一个烷基链（CH2）s，其中s代表1,2或3，其中该烷基链可以选择地被以下之一或多个取代：一个C1-4烷基基团，苯基或杂芳基；R5代表芳基，一个杂环基团或一个C3-8环烷基基团，该基团可以选择地与苯基或杂芳基融合；以及它们的光学异构体和拉氏体，以及其药学上可接受的盐；具有特定条件，制备这种化合物的方法，它们在治疗肥胖症、精神障碍、认知障碍、记忆障碍、精神分裂症、癫痫、以及相关疾病，以及神经系统疾病如痴呆症、多发性硬化症、帕金森病、亨廷顿舞蹈症、阿尔茨海默病和与疼痛相关的疾病的治疗中的用途，以及含有它们的药物组合物。
• Piperidine derivatives, compositions and use
  申请人：Imperial Chemical Industries PLC

  公开号：US05266570A1

  公开（公告）日：1993-11-30

  Compounds of formula I, Ia or Ib and pharmaceutically acceptable salts thereof, useful in the treatment of neuropsychiatric disorders such as psychoses; pharmaceutical compositions comprising a compound of formula I and a pharmaceutically acceptable diluent or carrier; and methods of treating neuropschiatric disorders comprising administering to a mammal (including man) in need of such treatment an effective amount of a compound of formula I, or a pharmaceutically acceptable salt thereof; ##STR1##

  公式I、Ia或Ib的化合物及其药学上可接受的盐，在治疗精神病等神经精神障碍方面有用；包括公式I化合物和药学上可接受的稀释剂或载体的药物组合物；以及治疗神经精神障碍的方法，包括向需要此类治疗的哺乳动物（包括人类）施用公式I化合物或其药学上可接受的盐的有效量；##STR1##
• Organic tricyclic compounds
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04224344A1

  公开（公告）日：1980-09-23

  Novel 9-aminoalkyl-methanoanthracenes of the formula: ##STR1## wherein A is C.sub.1 -C.sub.4 alkylene or C.sub.3 -C.sub.4 alkenylene and R.sub.1 and R.sub.2 are each hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.6 cycloalkyl(C.sub.1 -C.sub.3)alkyl, ar(C.sub.1 -C.sub.3)alkyl or polyhalo(C.sub.2 -C.sub.4)alkyl or, when taken together with the adjacent nitrogen atom, they may form a 5 to 7-membered nitrogen-containing heterocyclic ring which may contain an additional hetero atom, and their non-toxic salts, which are useful as anti-anxiety, anti-depressant, major tranquilizer, anti-histamine and anti-allergy drugs and can be prepared through a novel key intermediate, i.e., 9-formyl-9,10-dihydro-9,10-methanoanthracene, by various methods.

  新型9-氨基烷基-甲基蒽的化学式为：其中A为C.sub.1 -C.sub.4烷基或C.sub.3 -C.sub.4烯基，R.sub.1和R.sub.2分别为氢、C.sub.1 -C.sub.4烷基、C.sub.3 -C.sub.4烯基、C.sub.3 -C.sub.4炔基、C.sub.3 -C.sub.6环烷基(C.sub.1 -C.sub.3)烷基、ar(C.sub.1 -C.sub.3)烷基或多卤(C.sub.2 -C.sub.4)烷基，或者与相邻氮原子结合时，它们可以形成一个含氮的5至7元杂环，该环可能含有额外的杂原子，以及它们的无毒盐。这些化合物可用作抗焦虑、抗抑郁、镇静剂、抗组织胺和抗过敏药物，并可通过一种新型关键中间体制备，即9-甲酰基-9,10-二氢-9,10-甲基蒽，通过各种方法制备。
• 2-Morpholine containing methano or ethano anthracene compounds
  申请人：Sumitomo Chemical Company, Limited

  公开号：US04045560A1

  公开（公告）日：1977-08-30

  Novel morpholine compounds of the formula: ##STR1## wherein R.sub.1 represents hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.5 alkenyl, aryl(C.sub.1 -C.sub.4)alkyl or (C.sub.3 -C.sub.6)cycloalkyl(C.sub.1 -C.sub.4)alkyl and n represents 1 or 2, and their non-toxic salts, which are useful as antidepressants and can be produced by various methods.

  新型吗啡啉化合物的分子式：##STR1##其中R.sub.1代表氢、C.sub.1 -C.sub.4烷基、C.sub.3 -C.sub.5烯基、芳基(C.sub.1 -C.sub.4)烷基或(C.sub.3 -C.sub.6)环烷基(C.sub.1 -C.sub.4)烷基，n代表1或2，以及它们的无毒盐，可用作抗抑郁药，并可通过各种方法生产。