[2-[(4-氯苯基)甲基氨基]苯基]甲醇 | 123401-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [2-[(4-氯苯基)甲基氨基]苯基]甲醇
• 英文名称: o-(p-chlorobenzylamino)benzylalcohol
• 英文别名: (2-((4-chlorobenzyl)amino)phenyl)methanol；2-[[(4-chlorophenyl)methyl]amino]benzenemethanol；(2-{[(4-Chlorophenyl)methyl]amino}phenyl)methanol；[2-[(4-chlorophenyl)methylamino]phenyl]methanol
• CAS: 123401-94-5
• 化学式: C₁₄H₁₄ClNO
• mdl: MFCD12495890
• 分子量: 247.724
• InChiKey: GWRPWZUIVBRRKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [2-[(4-氯苯基)甲基氨基]苯基]甲醇 在 硫酸 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 9-Chloro-11H-dibenzo[b,e]azepine 5-oxide
  参考文献：
  名称：

  Synthesis and structure–Activity relationship of 2-(aminoalkyl)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine derivatives: a novel series of 5-HT2A/2C receptor antagonists. Part 2

  摘要：

  DOI：

  10.1016/s0960-894x(01)00722-3
• 作为产物：
  描述：

  2-(4'-chlorophenyl)-1,2-dihydro-4H-3,1-benzoxazine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 [2-[(4-氯苯基)甲基氨基]苯基]甲醇
  参考文献：
  名称：

  Synthesis and structure–Activity relationship of 2-(aminoalkyl)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine derivatives: a novel series of 5-HT2A/2C receptor antagonists. Part 2

  摘要：

  DOI：

  10.1016/s0960-894x(01)00722-3

文献信息

• A new synthetic approach to 5-deazaflavin and 5-deaza-10-thiaflavin.
  作者：Xing CHEN、Kiyoshi TANAKA、Fumio YONEDA

  DOI：10.1248/cpb.38.612

  日期：——

  A novel, one-step synthesis of 5-deazaflavin developed, in which a [4+2]cycloaddition is presumably involved, to give the 5-deazaflavin derivative in moderate yield. This methodology was successfully applied to the stepwise preparation of its thio analogue, 5-deaza-10-thiaflavin, whose 1, 5-dihydro derivative was transformed into the corresponding sulfone in good yield.

  开发了一种新颖的一步合成5-去氟黄素的方法，其中可能涉及[4+2]环加成反应，以中等产率得到5-去氟黄素衍生物。这种方法成功应用于其硫类类似物5-去氟-10-硫黄素的逐步制备，其1,5-二氢衍生物转化为对应的磺酰胺，产率良好。
• A new synthetic method for the preparation of 5-deazaflavins and 5-deaza-10-oxaflavins
  作者：Xing Chen、Minako Nagata、Kiyoshi Tanaka、Fumio Yoneda

  DOI：10.1039/c39890000044

  日期：——

  The condensation of 6-chlorouracils with o-(substituted amino)benzyl alcohols and o-hydroxybenzyl alcohol gave directly 5-deazaflavin and 5-deaza-10-oxaflavin derivatives, respectively.

  6-氯尿嘧啶与邻-（取代的氨基）苄醇和邻-羟基苄醇的缩合分别直接得到5-脱氮杂黄酮和5-脱氮杂-10-氧杂黄酮衍生物。
• Substituted tetracyclic azepine derivatives
  申请人：Janssen Pharmaceutica N.V.

  公开号：US05552399A1

  公开（公告）日：1996-09-03

  This invention concerns the compounds of formula (I), the pharmaceutically acceptable salts and stereoisomeric forms thereof, and also the N-oxide forms thereof. ##STR1## wherein: R.sup.1 and R.sup.2 each independently are hydrogen; C.sub.1-6 alkyl; C.sub.1-6 alkylcarbonyl; trihalomethylcarbonyl; C.sub.1-6 alkyl substituted with hydroxy, C.sub.1-6 alkyloxy, carboxyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkyloxycarbonyl or aryl; or R.sup.1 and R.sup.2 taken together with the nitrogen atom to which they are attached may form a morpholinyl ring or an optionally substituted heterocycle; R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.9, R.sup.10, R.sup.11 or R.sup.12 each independently are hydrogen, halo, cyano, hydroxy, trifluoromethyl, trifluoromethoxy, carboxyl, nitro, amino, mono- or di(C.sub.1-6 alkyl)-amino, C.sub.1-6 alkylcarbonylamino, aminosulfonyl, mono- or di(C.sub.1-6 alkyl)-aminosulfonyl, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkyloxy-carbonyl; R.sup.7 and R.sup.8 are each independently hydrogen, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy or R.sup.7 and R.sup.8 taken together may form mono- or di(cyano)methylene, or together with the carbon atom to which they are attached form a carbonyl or a spiro substituent; or R.sup.7 and R.sup.8 taken together may form methylene; R.sup.13 is hydrogen, C.sub.1-6 alkyl, or trifluoromethyl; R.sup.14 is hydrogen, C.sub.1-6 alkyl, cyano, or trifluoromethyl; n is zero to 6. These compounds were tested as mCPP-antagonists in rats. The compounds of formula (I) may be used as therapeutic agents in the treatment or the prevention of CNS disorders, cardiovascular disorders or gastrointestinal disorders.

  这项发明涉及式(I)的化合物，其药学上可接受的盐和立体异构体，以及它们的N-氧化物形式。其中：R.sup.1和R.sup.2分别独立地是氢；C.sub.1-6烷基；C.sub.1-6烷基羰基；三卤甲基羰基；带有羟基、C.sub.1-6烷氧基、羧基、C.sub.1-6烷基羰氧基、C.sub.1-6烷氧羰基或芳基的C.sub.1-6烷基；或者R.sup.1和R.sup.2与它们所连接的氮原子一起可以形成吗啡啉环或一个可选择地取代的杂环；R.sup.3、R.sup.4、R.sup.5、R.sup.6、R.sup.9、R.sup.10、R.sup.11或R.sup.12分别独立地是氢、卤、氰、羟基、三氟甲基、三氟甲氧基、羧基、硝基、氨基、单或双(C.sub.1-6烷基)-氨基、C.sub.1-6烷基羰胺基、氨基磺酰基、单或双(C.sub.1-6烷基)-氨基磺酰基、C.sub.1-6烷基、C.sub.1-6烷氧基、C.sub.1-6烷基羰基、C.sub.1-6烷氧羰基；R.sup.7和R.sup.8各自独立地是氢、羟基、C.sub.1-6烷基、C.sub.1-6烷氧基或R.sup.7和R.sup.8一起可以形成单或双(氰)亚甲基，或者与它们连接的碳原子一起形成羰基或螺旋取代基；或者R.sup.7和R.sup.8一起可以形成亚甲基；R.sup.13是氢、C.sub.1-6烷基或三氟甲基；R.sup.14是氢、C.sub.1-6烷基、氰或三氟甲基；n为0到6。这些化合物在大鼠中作为mCPP拮抗剂进行了测试。式(I)的化合物可用作治疗或预防中枢神经系统疾病、心血管疾病或消化系统疾病的治疗剂。
• Chemodivergent Spirocyclization of 2‐Sec‐Aminobenzilidene Imidazolones: Lewis Versus Brønsted Acids Catalysis
  作者：Dmitrii S. Ivanov、Elvira R. Zaitseva、Alexander Yu. Smirnov、Dina A. Rustamova、Andrey A. Mikhaylov、Maria A. Sycheva、Darya A. Gluschenko、Nadezhda S. Baleeva、Mikhail S. Baranov

  DOI：10.1002/adsc.202200109

  日期：2022.4.26

  Benzylidene imidazolones with ortho- secondary aminogroup undergo acid-promoted chemodivergent spirocyclization. Strong Lewis acids provide access to spirocyclic tetrahydroquinolines via [1,5]-hydride shift triggered cyclization despite of the presence of free secondary amino group. Brønsted acids promote unprecedented intramolecular umpolung hydroamination reaction with the formation of spirocyclic indolines

  具有邻仲氨基的亚苄基咪唑酮经历酸促进的化学发散螺环化。尽管存在游离的仲氨基，但强路易斯酸通过 [1,5]-氢化物移位触发的环化作用提供了获得螺环四氢喹啉的途径。布朗斯台德酸促进前所未有的分子内 umpolung 加氢胺化反应，形成螺环二氢吲哚。每个过程都以排他的原子经济方式进行。
• [EN] SUBSTITUTED TETRACYCLIC AZEPINE DERIVATIVES WHICH HAVE AFFINITY FOR 5-HT2 RECEPTORS<br/>[FR] DERIVES D'AZEPINE TETRACYCLIQUE SUBSTITUES, PRESENTANT UNE AFFINITE POUR LES RECEPTEURS 5-HT2
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：WO1996014320A1

  公开（公告）日：1996-05-17

  (EN) This invention concerns the compounds of formula (I), the pharmaceutically acceptable salts and stereoisomeric forms thereof, and also the $i(N)-oxide forms thereof. In formula (I) R1 and R2 each independently are hydrogen; C1-6alkyl; C1-6alkylcarbonyl; trihalomethylcarbonyl; C1-6alkyl substituted with hydroxy, C1-6alkyloxy, carboxyl, C1-6alkylcarbonyloxy, C1-6alkyloxycarbonyl or aryl; or R1 and R2 taken together with the nitrogen atom to which they are attached may form a morpholinyl ring or an optionally substitued heterocycle; R3, R4, R5, R6, R9, R10, R11 or R12 each independently are hydrogen, halo, cyano, hydroxy, trifluoromethyl, trifluoromethoxy, carboxyl, nitro, amino, mono- or di(C1-6alkyl)-amino, C1-6alkylcarbonylamino, aminosulfonyl, mono- or di(C1-6alkyl)-aminosulfonyl, C1-6alkyl, C1-6alkyloxy, C1-6alkylcarbonyl, C1-6alkyloxy-carbonyl; R7 and R8 are each independently hydrogen, hydroxy, C1-6alkyl, C1-6alkyloxy or R7 and R8 taken together may form mono- or di(cyano)methylene, or together with the carbon atom to which they are attached form a carbonyl or a spiro substituent; or R7 and R8 taken together may form methylene; R13 is hydrogen, C1-6alkyl, or trifluoromethyl; R14 is hydrogen, C1-6alkyl, cyano, or trifluoromethyl; n is zero to 6. These compounds were tested as mCPP-antagonists in rats. The compounds of formula (I) may be used as therapeutic agents in the treatment or the prevention of CNS disorders, cardiovascular disorders or gastrointestinal disorders.(FR) La présente invention concerne les composés représentés par la formule générale (I), leurs sels acceptables du point de vue pharmaceutique, leurs formes stéréo-isomères, ainsi que leurs formes $i(N)-oxyde. Dans cette formule R1 et R2 sont chacun indépendamment hydrogène, C1-6alkyle, C1-6alkylocarbonyle, trihalométhylocarbonyle, C1-6alkyle substitué par un hydroxy, par un C1-6alkylocarbonyloxy, par un C1-6alkylocarbonyle, ou par un aryle; ou bien, R1 et R2 pris ensemble avec l'atome d'azote auquel ils sont attachés peuvent former un noyau morpholinyle ou un hétérocycle éventuellement substitué; R3, R4, R5, R6, R9, R10, R11 ou R12 sont chacun indépendamment hydrogène, halo, cyano, hydroxy, trifluorométhyle, trifluorométhoxy, carboxyle, nitro, amino, mono- ou di(C1-6alkyl)-amino, C1-6alkylocarbonylamino, aminosulfonyle, mono- ou di(C1-6alkyl)-aminosulfonyle, C1-6alkyloxy-carbonyle; R7 et R8 sont chacun indépendamment hydrogène, hydroxy, C1-6alkyle, C1-6alkyloxy, ou bien R7 et R8 pris ensemble peuvent former un mono- ou di(cyano)méthylène, ou former, avec l'atome de carbone auquel ils sont attachés, un substitut carbonyle ou spiro; en outre, R7 et R8 pris ensemble peuvent former un méthylène; R13 est hydrogène, C1-6alkyle ou trifluorométhyle; R14 est hydrogène, C1-6alkyle, cyano ou trifluorométhyle; n est un entier valant de zéro à 6. Ces composés ont été testés chez le rat comme antagonistes CPPm. Ces composés de la formule (I) sont utilisables comme agents thérapeutiques dans le traitement ou la prévention des troubles du système nerveux central, des troubles cardio-vasculaires ou des troubles gastro-intestinaux.

  本发明涉及式（I）的化合物，其在药学上可接受的盐和立体异构体形式，以及其$i(N)-氧化物形式。在式（I）中，R1和R2各自独立地为氢; C1-6烷基; C1-6烷基羰基; 三卤甲基羰基; C1-6烷基取代羟基，C1-6烷氧基，羧基，C1-6烷基羰氧基，C1-6烷氧羰基或芳基; 或R1和R2与它们连接的氮原子一起可以形成吗啡啶环或可选择取代的杂环; R3、R4、R5、R6、R9、R10、R11或R12各自独立地为氢、卤、氰、羟基、三氟甲基、三氟甲氧基、羧基、硝基、氨基、单或双（C1-6烷基）-氨基，C1-6烷基羰基胺基，氨基磺酰基，单或双（C1-6烷基）-氨基磺酰基，C1-6烷基，C1-6烷氧基，C1-6烷基羰基，C1-6烷氧羰基; R7和R8各自独立地为氢，羟基，C1-6烷基，C1-6烷氧基或R7和R8一起可以形成单或双（氰）亚甲基，或与它们连接的碳原子一起形成羰基或螺旋取代基; 或R7和R8一起可以形成亚甲基; R13为氢，C1-6烷基或三氟甲基; R14为氢，C1-6烷基，氰或三氟甲基; n为0到6。这些化合物在大鼠中作为mCPP拮抗剂进行了测试。式（I）的化合物可用作治疗或预防中枢神经系统疾病、心血管疾病或胃肠道疾病的治疗剂。