N-(6-methoxyindan-1-ylmethyl)amine | 108048-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: N-(6-methoxyindan-1-ylmethyl)amine
• 英文别名: (6-methoxy-2,3-dihydro-1H-inden-1-yl)methanamine
• CAS: 108048-25-5
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: SJTLKMRJESNHKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(6-methoxyindan-1-ylmethyl)amine 在 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 N-(6-methoxy-indan-1-ylmethyl)-propionamide
  参考文献：
  名称：

  Synthesis of benzocycloalkane derivatives as new conformationally restricted ligands for melatonin receptors

  摘要：

  Benzocycloalkane derivatives 1-4 were synthesized as new conformationally restricted melatoninergic ligands. They were prepared by rite reaction of the ketones 5 with diethylcyanophosphonate and the reduction of the corresponding cyano compounds or by the Wittig reaction and Curtius degradation to obtain the amines 8. The 1-Cyanobenzocyclobutane derivative was obtained by the benzyne cyclisation reaction. The amines 8 were acylated with acetyl, propionyl or butyryl groups. The affinity of the compounds for chicken brain melatonin receptors was evaluated using 2-[I-125]-iodomelatonin as the radioligand The indanyl (2b,c) tetralin (3a-c) and benzocycloheptane (4c) derivatives were potent compounds with nanomolar affinity and an important enantioselectivity of the receptor was observed with the (+) enantiomers 2b and 3b. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00601-5
• 作为产物：
  描述：

  6-甲氧基-1-茚酮 在 镍 ammonium hydroxide 、 sodium tetrahydroborate 、 甲烷磺酸 、 锂丁酯 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 N-(6-methoxyindan-1-ylmethyl)amine
  参考文献：
  名称：

  Synthesis of benzocycloalkane derivatives as new conformationally restricted ligands for melatonin receptors

  摘要：

  Benzocycloalkane derivatives 1-4 were synthesized as new conformationally restricted melatoninergic ligands. They were prepared by rite reaction of the ketones 5 with diethylcyanophosphonate and the reduction of the corresponding cyano compounds or by the Wittig reaction and Curtius degradation to obtain the amines 8. The 1-Cyanobenzocyclobutane derivative was obtained by the benzyne cyclisation reaction. The amines 8 were acylated with acetyl, propionyl or butyryl groups. The affinity of the compounds for chicken brain melatonin receptors was evaluated using 2-[I-125]-iodomelatonin as the radioligand The indanyl (2b,c) tetralin (3a-c) and benzocycloheptane (4c) derivatives were potent compounds with nanomolar affinity and an important enantioselectivity of the receptor was observed with the (+) enantiomers 2b and 3b. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00601-5

文献信息

• Hydropyridine derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US04833169A1

  公开（公告）日：1989-05-23

  Hydropyridine derivatives of the formula ##STR1## in which R.sub.1 represents carboxy, lower alkoxycarbonyl, carbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl, R.sub.2 represents hydrogen, an optionally etherified or acylated hydroxy group or an optionally acylated amino group, and R.sub.3 represents a radical of the formula R-- (Ia), R--alk.sub.1 -- (Ib) or R'.dbd.alk.sub.2 -- (Ic) in which R represents a benzocycloalkenyl radical having a total of from 8 to 12 ring carbon atoms which is bonded via a saturated carbon atom and which is unsubstituted or is mono- or poly-substituted in the benzo moiety by hydroxy, lower alkoxy, lower alkanoyloxy, halogen, lower alkyl and/or by trifluoromethyl, and/or subsituted in the .alpha.-position by lower alkyl, and R' represents a benzocycloalkylidene radical having a total of from 8 to 12 ring carbon atoms which is unsubstituted or is mono- or poly-substituted in the benzo moiety by hydroxy, lower alkoxy, lower alkanoyloxy, halogen, lower alkyl and/or by trifluoromethyl, and alk.sub.1 represents lower alkylene or lower alkylidene and alk.sub.2 represents lower alkyl-.omega.-ylidene, wherein the dotted line is intended to show that there may be a single bond or especially a double bond, and 3-aminopropionic acid compounds of the formula R.sub.3 --NH--CH.sub.2 CH.sub.2 --R.sub.1 (IVc) in which R.sub.1 and R.sub.3 have the meanings given above, and their pharmaceutically acceptable salts, have nootropic properties and can be used as nootropic active ingredients in medicaments. They are manufactured by methods known per se.

  公式为##STR1##的吡啶衍生物，其中R.sub.1代表羧基、较低的烷氧羰基、氨基甲酰、N-较低烷基氨基甲酰或N,N-二较低烷基氨基甲酰，R.sub.2代表氢、可选择乙酰化或酰化的羟基或可选择酰化的氨基，R.sub.3代表公式R--（Ia）、R--alk.sub.1 --（Ib）或R'.dbd.alk.sub.2 --（Ic）的基团，其中R代表具有总共8至12个环碳原子的苯并环己烯基基团，通过饱和碳原子连接，并且在苯环上未被取代或者在苯基上被羟基、较低烷氧基、较低烷酰氧基、卤素、较低烷基和/或三氟甲基单取代或多取代，或者在α-位置被较低烷基取代；R'代表具有总共8至12个环碳原子的苯并环己基亚甲基基团，未被取代或者在苯基上被羟基、较低烷氧基、较低烷酰氧基、卤素、较低烷基和/或三氟甲基单取代或多取代，alk.sub.1代表较低烷基或较低烷基亚甲基，alk.sub.2代表较低烷基-ω-亚甲基，其中虚线表示可能存在单键或特别是双键，以及公式为R.sub.3 --NH--CH.sub.2 CH.sub.2 --R.sub.1（IVc）的3-氨基丙酸化合物，其中R.sub.1和R.sub.3具有上述给定的含义，及其药学上可接受的盐，具有智力增强作用，可用作药物中的智力增强活性成分。它们通过已知方法制造。
• Hydropyridin-Derivate
  申请人：CIBA-GEIGY AG

  公开号：EP0213080A2

  公开（公告）日：1987-03-04

  Hydropyridin-Derivate der Formel worin R, Carboxy, Niederalkoxycarbonyl, Carbamoyl, N-Niederalkylcarbamoyl oder N,N-Diniederalkylcarbamoyl bedeutet, R, Wasserstoff, eine gegebenenfalls verätherte oder acylierte Hydroxygruppe oder eine gegebenenfalls acylierte Aminogruppe bedeutet und R3 einen Rest der Formeln R-(la), R-alk,- (Ib) oder R'=alk2- (Ic) bedeutet, in der R einen unsubstituierten oder im Benzoteil ein- oder mehrfach durch Hydroxy, Niederalkoxy, Niederalkanoyloxy, Halogen, Niederalkyl und/oder Trifluormethyl und/oder in a-Stellung durch Niederalkyl substituierten, über ein gesättigtes C-Atom gebundenen Benzocycloalkenylrest mit insgesamt 8 bis 12 Ring-C-Atomen bzw. R' einen unsubstituierten oder im Benzoteil ein- oder mehrfach durch Hydroxy, Niederalkoxy, Niederalkanoyloxy, Halogen, Niederalkyl und/oder Trifluormethyl substituierten Benzocycloalkylidenrest mit insgesamt 8 bis 12 Ring-C-Atomen bedeutet, und alk, Niederalkylen oder Niederalkyliden bzw. alk, Niederalkyl-ω-yliden bedeutet, wobei die gestrichelte Linie zum Ausdruck bringen soll, dass eine Einfach- oder insbesondere Doppelbindung vorliegen kann, sowie 3-Aminopropionsäureverbindungen der Formel R3―NH―CH2CH2-―R, (IVc), woring R, und R, obige Bedeutungen haben, und ihre pharmazeutisch verwendbaren Salze haben nootrope Eigenschaften und können als nootrope Arzneimittelwirkstoffe verwendet werden. Sie werden nach an sich bekannten Methoden hergestellt.

  式中的氢吡啶衍生物 其中 R 是羧基、低级烷氧羰基、氨基甲酰基、N-低级烷基氨基甲酰基或 N,N-二低级烷基氨基甲酰基，R 是氢、任选醚化或酰化的羟基或任选酰化的氨基，R3 是式 R-(la)、R-alk,- (Ib)或 R'=alk2- (Ic)的基、其中 R 是一个苯环烯基，该基在苯偶氮基上未被羟基、低级烷氧基、低级烷酰氧基、卤素、低级烷基和/或三氟甲基和/或在 a 位上被低级烷基取代，并通过一个饱和碳原子键合，共有 8 至 12 个环状碳原子，或R'表示苯环亚烷基，该基在苯偶氮基上未被羟基、低级烷氧基、低级烷酰氧基、卤素、低级烷基和/或三氟甲基取代，或被单取代或被多取代，且总共具有 8 至 12 个环 C 原子，以及烷基、低级亚烷基或低级亚烷基，或式 R3-NH-CH2CH2--R，(IVc)，其中 R 和 R 具有上述含义的 3-氨基丙酸化合物及其药用盐具有促智特性，可用作促智活性药物成分。它们是通过已知方法生产的。
• US4833169A
  申请人：——

  公开号：US4833169A

  公开（公告）日：1989-05-23
• US4939160A
  申请人：——

  公开号：US4939160A

  公开（公告）日：1990-07-03
• Synthesis of benzocycloalkane derivatives as new conformationally restricted ligands for melatonin receptors
  作者：S. Kloubert、M. Mathé-Allainmat、J. Andrieux、S. Sicsic、M. Langlois

  DOI：10.1016/s0960-894x(98)00601-5

  日期：1998.12

  Benzocycloalkane derivatives 1-4 were synthesized as new conformationally restricted melatoninergic ligands. They were prepared by rite reaction of the ketones 5 with diethylcyanophosphonate and the reduction of the corresponding cyano compounds or by the Wittig reaction and Curtius degradation to obtain the amines 8. The 1-Cyanobenzocyclobutane derivative was obtained by the benzyne cyclisation reaction. The amines 8 were acylated with acetyl, propionyl or butyryl groups. The affinity of the compounds for chicken brain melatonin receptors was evaluated using 2-[I-125]-iodomelatonin as the radioligand The indanyl (2b,c) tetralin (3a-c) and benzocycloheptane (4c) derivatives were potent compounds with nanomolar affinity and an important enantioselectivity of the receptor was observed with the (+) enantiomers 2b and 3b. (C) 1998 Elsevier Science Ltd. All rights reserved.