1-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-3-yl)propan-2-one | 41635-19-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-3-yl)propan-2-one
• CAS: 41635-19-2
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: QUQVUQQLKRORNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-3-yl)propan-2-one 在 sodium hydroxide 、 硫酸 作用下， 生成 2-methyl-1-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-3-yl)propan-2-amine
  参考文献：
  名称：

  Vejdelek,Z.J. et al., Collection of Czechoslovak Chemical Communications, 1972, vol. 37, p. 3136 - 3143

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yl)acetonitrile 在 硫酸 、 sodium methylate 作用下， 生成 1-(6,7,8,9-tetrahydro-5H-benzo[7]annulen-3-yl)propan-2-one
  参考文献：
  名称：

  Vejdelek,Z.J. et al., Collection of Czechoslovak Chemical Communications, 1972, vol. 37, p. 3136 - 3143

  摘要：

  DOI：

文献信息

• BENZAZEPINE DERIVATIVES AND THEIR USE AS HISTAMINE H3 ANTAGONISTS
  申请人：Pooni Parminder Kaur

  公开号：US20110124626A1

  公开（公告）日：2011-05-26

  A compound having the formula (1) wherein: R1 is a group selected from C 3-8 cycloalkyl, C 1-6 alkyl, C 1-6 alkylene-C 3-8 cycloalkyl, each of which groups may optionally be substituted with C 1-6 alkyl, halogen, haloC 1-6 alkyl or OR15, or R1 is heterocyclyl, optionally substituted with C 1-6 alkyl, haloC 1-6 alkyl or OR15; n is 0, 1, 2, 3 or 4, the alkylene group —(CH 2 ) m — formed thereby being optionally substituted with a group selected from C 1-4 alkyl, C 3-8 cycloalkyl and arylsulfonyl; A is a group selected from —N(R2)CO—, —CON(R2)-, —OC(O)—, —C(O)O—, —CO—, —C(R2)(OR3)-, —C(═N—O—R3)-, —C(═CR2R3)-, —C 3-8 cycloalkylene-, —C(R2)(haloC 1-6 alkyl)-, C 1-4 alkylene and —C(OR3)(haloC 1-6 alkyl)-; R2 and R3 are each independently selected from H, C 1-6 alkyl, and C 3-8 cycloalkyl, or, when A is —N(R2)CO— and X is absent, R2 may form, together with the adjacent nitrogen atom and Z, an N-containing heterocyclyl group, which may optionally be substituted; X is absent or is C14 alkylene or C24 alkenylene, each of which may optionally be substituted with one or more C 1-4 alkyl groups, OR16, halogen or haloC 1-6 alkyl; Z is selected from aryl, heteroaryl, C 3-8 cycloalkyl, and heterocyclyl, each of which may optionally be substituted by a group selected from —Y-aryl, heteroaryl, —Y—C 3-8 cycloalkyl and —Y-heterocyclyl, or, when X is present, Z may be H, or, when X is absent and A is —C(R2)(OR3)- or —N(R2)CO—, Z may be H, or, when A is —N(R2)CO— and X is absent, Z may form, together with the adjacent nitrogen atom and R2, an N-containing heterocyclyl group which may optionally be substituted, wherein, when A is —CO—, Z is linked to X or A via a carbon atom and wherein, when A is —N(R2)CO— and Z is H, R1 is C 3-8 cycloalkyl; and Y represents a bond, C 1-6 alkylene, CO, NR14, COC 2-6 alkenylene, O, SO 2 or NHCOC 1-6 alkylene; wherein said cycloalkyl, aryl, heteroaryl and heterocyclyl groups Z may be optionally substituted by one or more substituents which may be the same or different, and which are selected from halogen, haloC 1-6 alkyl, hydroxy, cyano, nitro, ═O, —R4, —CO 2 R4, —COR4, —NR5R6, —C 1-6 alkyl-NR5R6, —C 3-8 cycloalkyl-NR5R6, —CONR12R13, —NR12COR13, —NR5SO 2 R6, —OCONR5R6, —NR5CO 2 R6, —NR4CONR5R6 or —SO 2 NR5R6-SHR8, -alkyl-OR8, —SOR8, —OR9, —SO2R9, —OSO 2 R9, -alkyl-SO 2 R9, -alkyl-CONHR9, -alkyl-SONHR9, -alkyl-COR10, —CO-alkyl-R10, —O-alkyl-R11 (wherein R4, R5 and R6 independently represent hydrogen, C 1-6 alkyl, —C 3-8 cycloalkyl, —C 1-6 alkylene-C 3-8 cycloalkyl, aryl, heterocyclyl or heteroaryl, wherein R8 represents C 1-6 alkyl, wherein R9 represents C 1-6 alkyl or aryl, wherein R10 represents aryl, wherein R11 represents C 3-8 cycloalkyl or aryl, R12, R13, R14, R15 and R16 each independently represent H or C 1-6 alkyl, and wherein —NR5R6 and —NR12R13 may represent a nitrogen containing heterocyclyl group); wherein said R4, R5, R6 R8, R9, R11 and R11 groups may be optionally substituted by one or more substituents which may be the same or different, and which are selected from the group consisting of halogen, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, cyano, amino, ═O or trifluoromethyl; and wherein substituents of Z selected from —Y-aryl, —Y-heteroaryl, —Y—C 3-8 cycloalkyl and —Y-heterocyclyl may be optionally substituted by one or more substituents selected from ═O, hydroxy, cyano, nitro, halogen, haloC 1-6 alkyl and C 1-6 alkyl; and wherein, when A is C 1-4 alkylene, said cycloalkyl, aryl, heteroaryl or heterocyclyl group Z (such as a heterocyclyl group Z) is substituted at least with hydroxy, CF 3 , or ═O; and wherein, when A is CON(R2) n is 1; or a pharmaceutically acceptable salt or ester thereof, provided that: when A is —CO—, R1 is CH 3 , C 3-8 cycloalkyl-substituted C 1-6 alkylene or n-butyl, n is 0 and X is —CH 2 CH 2 —, Z is not N-benzyl substituted 4-piperidinyl, N-(3-fluorobenzyl)-substituted 4-piperidinyl or N-acetyl substituted 4-piperidinyl; when A is —OC(O)—, R1 is cyclobutyl, n is 0 and X is —CH 2 CH 2 —, Z is not H; when A is —OC(O)—, R1 is n-propyl, n is 0 and X is —CH 2 —, Z is not H; and when A is —CO—, R1 is CH 3 , n is 0 and X is CH 2 , Z is not H.

  化合物的化学式为(1)，其中：R1是从C3-8环烷基，C1-6烷基，C1-6烷基-C3-8环烷基中选择的一个基团，每个基团可以选择性地被C1-6烷基，卤素，卤基C1-6烷基或OR15取代，或者R1是杂环基，可以选择性地被C1-6烷基，卤基C1-6烷基或OR15取代；n是0、1、2、3或4，由此形成的烷基基团-(CH2)m可以选择性地被从C1-4烷基、C3-8环烷基和芳基磺酰基中选择的一个基团取代；A是从-N(R2)CO-，-CON(R2)-，-OC(O)-，-C(O)O-，-CO-，-C(R2)(OR3)-，-C(═N-O-R3)-，-C(═CR2R3)-，-C3-8环烷基，-C(R2)(卤基C1-6烷基)-，C1-4烷基和-C(OR3)(卤基C1-6烷基)-中选择的一个基团；R2和R3各自独立地选择自H、C1-6烷基和C3-8环烷基，或者当A为-N(R2)CO-且X不存在时，R2可以与相邻的氮原子和Z一起形成一个N-含杂环基团，该基团可以选择性地被取代；X不存在或是C14烷基或C24烯基，每个基团可以选择性地被一个或多个C1-4烷基基团、OR16、卤素或卤基C1-6烷基取代；Z从芳基，杂芳基，C3-8环烷基和杂环基中选择，每个基团可以选择性地被从-Y-芳基、杂芳基、-Y-C3-8环烷基和-Y-杂环基中选择的一个基团取代，或者当X存在时，Z可以是H，或者当X不存在且A为-C(R2)(OR3)-或-N(R2)CO-时，Z可以是H，或者当A为-N(R2)CO-且X不存在时，Z可以与相邻的氮原子和R2一起形成一个可以选择性地被取代的N-含杂环基团，在A为-CO-时，Z通过一个碳原子与X或A连接，在A为-N(R2)CO-且Z为H时，R1为C3-8环烷基；Y表示一个键，C1-6烷基，CO，NR14，COC2-6烯基，O，SO2或NHCOC1-6烷基；其中所述的环烷基，芳基，杂芳基和杂环基Z可以选择性地被一个或多个取代基取代，所述取代基可以是相同的或不同的，所述取代基从卤素、卤基C1-6烷基、羟基、氰基、硝基、═O、-R4、-CO2R4、-COR4、-NR5R6、-C1-6烷基-NR5R6、-C3-8环烷基-NR5R6、-CONR12R13、-NR12COR13、-NR5SO2R6、-OCONR5R6、-NR5CO2R6、-NR4CONR5R6或-SO2NR5R6-SHR8、-烷基-OR8、-SOR8、-OR9、-SO2R9、-OSO2R9、-烷基-SO2R9、-烷基-CONHR9、-烷基-SONHR9、-烷基-COR10、-CO-烷基-R10、-O-烷基-R11中选择（其中R4、R5和R6独立地表示氢、C1-6烷基、-C3-8环烷基、-C1-6烷基-C3-8环烷基、芳基、杂环基或杂芳基，其中R8表示C1-6烷基，其中R9表示C1-6烷基或芳基，其中R10表示芳基，其中R11表示C3-8环烷基或芳基，R12、R13、R14、R15和R16各自独立地表示H或C1-6烷基，其中-NR5R6和-NR12R13可以表示一个含氮杂环基团）；其中所述的Z选择自-Y-芳基、-Y-杂芳基、-Y-C3-8环烷基和-Y-杂环基中选择的一个，所述基团可以选择性地被一个或多个取代基取代，所述取代基选择自═O、羟基、氰基、硝基、卤素、卤基C1-6烷基和C1-6烷基；当A为C1-4烷基时，所述的环烷基、芳基、杂芳基或杂环基Z（如杂环基Z）至少被羟基、CF3或═O取代；当A为CON(R2)时，n为1；或其药学上可接受的盐或酯，前提是：当A为-CO-时，R1为CH3，C3-8环烷基取代的C1-6烷基或正丁基，n为0，X为-CH2CH2-，Z不是N-苄基取代的4-哌啶基、N-(3-氟苄基)-取代的4-哌啶基或N-乙酰取代的4-哌啶基；当A为-OC(O)-时，R1为环丁基，n为0，X为-CH2CH2-，Z不是H；当A为-OC(O)-时，R1为正丙基，n为0，X为-CH2-，Z不是H；当A为-CO-时，R1为CH3，n为0，X为CH2，Z不是H。
• Vejdelek,Z.J. et al., Collection of Czechoslovak Chemical Communications, 1972, vol. 37, p. 3136 - 3143
  作者：Vejdelek,Z.J. et al.

  DOI：——

  日期：——