7-nitro-1,2-dihydronaphthalene | 67090-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-nitro-1,2-dihydronaphthalene
• 英文别名: 1,2-dihydro-7-nitro-naphthalene；6-nitro-1,2-dihydronaphthalene
• CAS: 67090-45-3
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: SBMDVBRLMNDQDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  47-48 °C(Solv: hexane (110-54-3))
• 沸点：
  290.9±29.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-nitro-1,2-dihydronaphthalene 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 生成 trans-2-bromo-6-nitro-1,2,3,4-tetrahydro-1-naphthalenol
  参考文献：
  名称：

  1,2-N-烷基亚氨基-1,2,3,4-四氢萘衍生物的合成和沙丁胺醇作为新的β-肾上腺素能受体的闭环类似物的制备。

  摘要：

  描述了一种制备5-取代2-叔烷基氨基-6-羟基-1,2,3,4-四氢-1-萘酚的方法。该方法包括由2-溴-1-羟基衍生物通过1, 2-环氧化物制备1-烷基氨基-2-羟基-1,2,3,4-四氢萘，然后将1-烷基氨基和2-羟基转位基团通过闭环形成1, 2-氮丙啶。详细研究了环氧化物和氮丙啶的形成以及环氧化物与胺的反应。环氧化物的开环反应具有区域选择性，亲核试剂的攻击位置不受苯环上取代基的电子效应影响。环化成氮丙啶环最好通过 Wenker 方法使用三氧化硫-三乙胺加合物作为硫酸化剂来完成。使用我们的方法，合成了反式-2-叔丁基氨基-6-羟基-5-羟甲基-1,2,3,4-四氢-1-萘酚 (70)，作为沙丁胺醇的构象固定类似物。

  DOI：

  10.1248/cpb.26.394
• 作为产物：
  描述：

  6-硝基-Alpha-四氢萘酮 在 sodium tetrahydroborate 、 potassium hydrogensulfate 作用下， 生成 7-nitro-1,2-dihydronaphthalene
  参考文献：
  名称：

  1,2-N-烷基亚氨基-1,2,3,4-四氢萘衍生物的合成和沙丁胺醇作为新的β-肾上腺素能受体的闭环类似物的制备。

  摘要：

  描述了一种制备5-取代2-叔烷基氨基-6-羟基-1,2,3,4-四氢-1-萘酚的方法。该方法包括由2-溴-1-羟基衍生物通过1, 2-环氧化物制备1-烷基氨基-2-羟基-1,2,3,4-四氢萘，然后将1-烷基氨基和2-羟基转位基团通过闭环形成1, 2-氮丙啶。详细研究了环氧化物和氮丙啶的形成以及环氧化物与胺的反应。环氧化物的开环反应具有区域选择性，亲核试剂的攻击位置不受苯环上取代基的电子效应影响。环化成氮丙啶环最好通过 Wenker 方法使用三氧化硫-三乙胺加合物作为硫酸化剂来完成。使用我们的方法，合成了反式-2-叔丁基氨基-6-羟基-5-羟甲基-1,2,3,4-四氢-1-萘酚 (70)，作为沙丁胺醇的构象固定类似物。

  DOI：

  10.1248/cpb.26.394

文献信息

• Synthesis of functionalized 2,3-dihydropyrroles by oxidative radical cyclization of N-Sulfonyl β-enamino esters with alkenes
  作者：Masahiro Yoshida、Asuka Kobayashi、Atsushi Nakayama、Kosuke Namba

  DOI：10.1016/j.tet.2016.03.055

  日期：2016.5

  N-sulfonyl β-enamino esters with alkenes has been developed. Substituted 2,3-dihydropyrroles were produced when the reactions were carried out in the presence of CAN and Cu(OAc)2 as the oxidant. Intramolecular cyclization of β-enamino carbonyl compounds having an alkenyl and an alkynyl side chain proceeded to afford the corresponding bicyclic products, respectively.

  已经开发出N-磺酰基β-烯氨基酯与烯烃的氧化自由基环化。当在CAN和Cu（OAc）2作为氧化剂存在下进行反应时，会生成取代的2,3-二氢吡咯。具有烯基和炔基侧链的β-烯氨基羰基化合物的分子内环化分别进行，得到相应的双环产物。
• 5-Methyl-1-(naphthalen-2-YL)-1H-Pyrazoles useful as sigma receptor inhibitors
  申请人：Laboratorios Del. Dr. Esteve, S.A.

  公开号：EP2113501A1

  公开（公告）日：2009-11-04

  Compounds having the formula (I): wherein the dashed line (represented by - - - - - ) represents an optional double bond; R1 is hydrogen and R2 is hydroxyethyl; or R1 and R2 together with the nitrogen atom to which they are attached form a morpholinyl ring optionally substituted with one or two hydroxy groups; R3 is hydroxy or C1-6alkoxy; n is selected from 0, 1, and 2; with the proviso that the combination where the dashed line represents a double bond, R1 and R2 together with the nitrogen atom to which they are attached form a morpholinyl ring, and n is 0, is excluded; and an N-oxide, salt, or stereoisomer thereof. Also provided are methods for the preparation of compounds of formula (I); their uses as a medicament, particularly for the treatment or prophylaxis of a sigma receptor mediated disease or condition.

  具有以下结构式（I）的化合物： 其中虚线（表示为- - - - -）代表可选的双键； R1为氢，R2为羟乙基；或者R1和R2与它们附着的氮原子一起形成一个吗啡啉环，该环可选择地被一个或两个羟基取代； R3为羟基或C1-6烷氧基； n选自0、1和2； 但是排除以下组合：虚线代表双键，R1和R2与它们附着的氮原子一起形成吗啡啉环，n为0； 以及其N-氧化物、盐或立体异构体。 此外，提供了制备结构式（I）化合物的方法；它们作为药物的用途，特别是用于治疗或预防σ受体介导的疾病或症状。
• Benzocyclohexanes and benzocycloheptanes useful as analgesics
  申请人：Roussel Uclaf

  公开号：US05130329A1

  公开（公告）日：1992-07-14

  Novel all possible enantiomeric and diastereoisomeric forms of compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms, --No.sub.2, --NH.sub.2 and mono and dialkylamino of 1 to 5 alkyl carbon atoms, A and B have the trans configuration, one of A and B being ##STR2## R.sub.2 is hydrogen or alkyl of 1 to 5 carbon atoms, Z is --(CH.sub.2).sub.n2, n.sub.2 being an integer from 0 to 5 or branched alkylene of 2 to 8 carbon atoms or --CH.sub.2 --O--, Y is selected from the group consisting of phenyl, naphthyl, indenyl, heteromonocycle of 5 to 6 ring atoms and heterobicycle, all optionally having at least one substituent and the other of A and B is ##STR3## R.sub.4 and R.sub.5 individually being selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken together with the nitrogen to which they are attached form a 5 to 6 ring heterocycle optionally containing a heteroatom selected from the group consisting of --O--, --S-- and --NH-- and their non-toxic, pharmaceutically acceptable acid addition salts having central analgesic properties and a strong affinity for opiate receptors.

  本发明涉及化合物的所有可能的对映体和二对映异构体形式，其化学式为##STR1##其中R.sub.1从氢、卤素、1到5个碳原子的烷基和烷氧基、--No.sub.2、--NH.sub.2和1到5个碳原子的单烷基和双烷基氨基中选择，A和B具有反构型，A和B中的一个为##STR2##R.sub.2为氢或1到5个碳原子的烷基，Z为--(CH.sub.2).sub.n2，n.sub.2为0到5的整数或2到8个碳原子的支链烷基或--CH.sub.2--O--，Y从苯基、萘基、茚基、5到6个环原子的杂环和杂环中选择，所有这些基团可选择地至少有一个取代基，A和B中的另一个为##STR3##R.sub.4和R.sub.5分别从氢和1到5个碳原子的烷基中选择，或者与它们连接的氮原子一起形成一个5到6环杂环，该杂环可选择地包含从--O--、--S--和--NH--中选择的杂原子，并且它们的无毒、药学上可接受的酸盐具有中枢镇痛特性和对阿片受体的强亲和力。
• Benzocyclohexanes and analgesic compositions thereof
  申请人：Roussel Uclaf

  公开号：US05068244A1

  公开（公告）日：1991-11-26

  Novel all possible enantiomeric and diastereoisomeric forms of compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 5 carbon atoms, --NO.sub.2, --NH.sub.2 and mono and dialkylamino of 1 to 5 alkyl carbon atoms, n is 1 or 2, A and B have the trans configuration, one of A and B being ##STR2## R.sub.2 is hydrogen or alkyl of 1 to 5 carbon atoms, Z is --(CH.sub.2)--.sub.n2, n.sub.2 being an integer from 0 to 5 or branched alkylene of 2 to 8 carbon atoms or --CH.sub.2 --O--, Y is selected from the group consisting of phenyl, naphthyl, indenyl, heteromonocycle of 5 to 6 ring atoms and heterobicycle, all optionally having at least one substituent and the other of A and B is ##STR3## R.sub.4 and R.sub.5 individually being selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken together with the nitrogen to which they are attached form a 5 to 6 ring heterocycle optionally containing a heteroatom selected from the group consisting of --O--, --S-- and --NH-- with the proviso 1) A is ##STR4## wherein R.sub.4 l and R.sub.5 have the above definitions and B is ##STR5## wherein R.sub.2, Z and Y have the above definition or 2) Z is --(CH.sub.2).sub.n2 -- and n.sub.2 is 0,2,3,4 or 5 or branched alkylene of 2 to 8 carbon atoms or --CH.sub.2 O-- yr 3) Y is phenyl substituted with at least one member of the group consisting of alkyl of 1 to 5 carbon atoms, alkoxy of 2 to 5 carbon atoms, --NH.sub.2 and mono and dialkylamino or 4) Y is naphthyl, indenyl, heteromonocycle of 5 to 6 ring atoms or heterobicycle, all optionally substituted with at least one substituent, except unsubstituted benzothiophene or 5) R.sub.1 is --NO.sub.2 or 6) R.sub.2 is alkyl of 4 to 5 carbon atoms or 7) R.sub.1 is hydrogen, n.sub.1 is 1, A is ##STR6## Y is selected from the group consisting of 3,4-dimethoxy-phenyl, 4-nitro-phenyl and benzothienyl and B is pyrrolidinyl or 8) R.sub.1 is hydrogen, n.sub.1 is 2, A is ##STR7## Y is selected from the group consisting of 3,4-dimethoxy-phenyl, 3,4-dichloro-phenyl, 4-trifluoromethyl-phenyl, 4-nitro-phenyl and benzothienyl and B is pyrrolidinyl and their non-toxic, pharmaceutically acceptable acid addition salts having central analgesic properties and a strong affinity for opiate receptors.

  本发明涉及一种化合物的所有可能的对映异构体和顺反异构体，该化合物的化学式为##STR1##其中R.sub.1选自氢、卤素、1至5个碳原子的烷基和烷氧基、--NO.sub.2、--NH.sub.2和1至5个烷基碳原子的单烷基和双烷基氨基，n为1或2，A和B具有反式构型，其中A和B中的一个为##STR2##R.sub.2为氢或1至5个碳原子的烷基，Z为--(CH.sub.2)--.sub.n2，n.sub.2为0至5的整数或2至8个碳原子的支链烷基或--CH.sub.2 --O--，Y选自苯基、萘基、茚基、5至6个环原子的杂环单环和杂环双环，所有这些都可以选择至少一个取代基，而A和B中的另一个为##STR3##其中R.sub.4和R.sub.5分别选自氢和1至5个碳原子的烷基，或与它们所连接的氮一起形成一个5至6个环的杂环，该杂环可以选择从--O--、--S--和--NH--中选择的一个杂原子，但是有以下规定：1）A为##STR4##其中R.sub.4和R.sub.5具有上述定义，B为##STR5##其中R.sub.2、Z和Y具有上述定义，或2）Z为--(CH.sub.2).sub.n2 --，n.sub.2为0、2、3、4或5或2至8个碳原子的支链烷基或--CH.sub.2 O--，或3）Y为至少有一个来自由1至5个碳原子的烷基、2至5个碳原子的烷氧基、--NH.sub.2和单烷基和双烷基氨基组成的群的取代基的苯基，或4）Y为萘基、茚基、5至6个环原子的杂环单环或杂环双环，所有这些都可以选择至少一个取代基，但不包括未取代的苯并噻吩，或5）R.sub.1为--NO.sub.2，或6）R.sub.2为4至5个碳原子的烷基，或7）R.sub.1为氢，n.sub.1为1，A为##STR6##Y选自3,4-二甲氧基苯基、4-硝基苯基和苯并噻吩，B为吡咯烷基，或8）R.sub.1为氢，n.sub.1为2，A为##STR7##Y选自3,4-二甲氧基苯基、3,4-二氯苯基、4-三氟甲基苯基、4-硝基苯基和苯并噻吩，B为吡咯烷基，以及它们的非毒性、药学上可接受的酸盐，具有中枢镇痛性和对阿片受体的强亲和力。
• 5-METHYL-1-(NAPHTHALEN-2-YL)-1H-PYRAZOLES USEFUL AS SIGMA RECEPTOR INHIBITORS
  申请人：Torrens Jover Antoni

  公开号：US20110118253A1

  公开（公告）日：2011-05-19

  The invention relates to compounds having the formula (I): wherein the dashed line (represented by - - - - -) represents an optional double bond; R 1 is hydrogen and R 2 is hydroxyethyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a morpholinyl ring optionally substituted with one or two hydroxy groups; each R 3 is independently hydroxy or C 1-6 alkoxy; n is selected from 0, 1, and 2; or a N-oxide, salt, prodrug, solvate or stereoisomer thereof; with the proviso that the compound where the dashed line represents a double bond, R 1 and R 2 together with the nitrogen atom to which they are attached form a morpholinyl ring, and n is 0, is excluded. Also provided are methods for the preparation of compounds of formula (I); their uses as a medicaments, particularly for the treatment or prophylaxis of a sigma receptor mediated diseases or conditions.

  本发明涉及具有以下公式（I）的化合物：其中虚线（表示为- - - - -）表示可选的双键；R1为氢，R2为羟乙基；或者R1和R2与它们所连接的氮原子一起形成一个吗啉环，该吗啉环可选择地被一个或两个羟基取代；每个R3独立地是羟基或C1-6烷氧基；n从0、1和2中选择；或其N-氧化物、盐、前药、溶剂或立体异构体；但是，当虚线表示双键，R1和R2与它们所连接的氮原子一起形成吗啉环，且n为0时，该化合物被排除。还提供了制备公式（I）化合物的方法；它们作为药物的用途，特别是用于治疗或预防σ受体介导的疾病或症状。