N-propyl-3-hydroxybenzylamine | 126845-31-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-propyl-3-hydroxybenzylamine
• 英文别名: 3-[(Propylamino)methyl]phenol；3-(propylaminomethyl)phenol
• CAS: 126845-31-6
• 化学式: C₁₀H₁₅NO
• mdl: MFCD09934064
• 分子量: 165.235
• InChiKey: CEMSAUZILJQSKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  N-propyl-3-hydroxybenzylamine 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 39.0h， 生成 Methyl-carbamic acid 3-({[3-(9-oxo-9H-xanthen-3-yloxy)-propyl]-propyl-amino}-methyl)-phenyl ester
  参考文献：
  名称：

  Acetylcholinesterase Inhibitors:  Synthesis and Structure−Activity Relationships of ω-[N-Methyl-N-(3-alkylcarbamoyloxyphenyl)- methyl]aminoalkoxyheteroaryl Derivatives

  摘要：

  Acetylcholinesterase (AChE) inhibitors are one of the most actively investigated classes of compounds in the search for an effective treatment of Alzheimer's disease. This work describes the synthesis, AChE inhibitory activity, and structure-activity relationships of some compounds related to a recently discovered series of AChE inhibitors: the omega-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)methyl]aminoalkoxyxanthen-9-ones. The influence of structural variations on the inhibitory potency was carefully investigated by modifying different parts of the parent molecule, and a theoretical model of the binding of one representative compound to the enzyme was developed. The biological properties of the series were investigated in some detail by considering not only the activity on isolated enzyme but the selectivity with respect to butyrylcholinesterase (BuChE) and the in vitro inhibitory activity on rat cerebral cortex as well. Some of the newly synthesized derivatives, when tested on isolated and/or AChE-enriched rat brain cortex fraction, displayed a selective inhibitory activity and were more active than physostigmine. In particular, compound 13, an azaxanthone derivative, displayed the best rat cortex AChE inhibition (190-fold higher than physostigmine), as well as a high degree of enzyme selectivity (over 60-fold more selective for AChE than for BuChE). When tested in the isolated enzyme, compound 13 was less active, suggesting some differences either in drug availability/biotransformation or in the inhibitor-sensitive residues of the enzyme when biologically positioned in rat brain membranes.

  DOI：

  10.1021/jm9810046
• 作为产物：
  描述：

  3-[(E)-Propyliminomethyl]-phenol 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N-propyl-3-hydroxybenzylamine
  参考文献：
  名称：

  Development of chemosensor for Sr²⁺using organic nanoparticles: application of sensor in product analysis for oral care

  摘要：

  开发了一系列新的化合物来识别金属离子，并且发现有机化合物中取代基的位置被证明是化学传感器开发的决定因素。采用再沉淀法在水介质中制备有机纳米粒子（ONP），ONP在水介质中的悬浮液可保持稳定1个月。使用荧光光谱研究了这些 ONP 的识别能力，只有化合物 1 的 ONP 产生了 Sr2+ 传感器，并且发现传感器活性不受任何其他阳离子存在的影响。该传感器已成功用于研究口腔凝胶以及用于治疗敏感牙齿的牙膏中的 Sr2+ 水平。

  DOI：

  10.1039/c4ob01234h

文献信息

• Process for producing enyne derivatives
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US05231183A1

  公开（公告）日：1993-07-27

  A process for producing an enyne derivative, and intermediate, which is useful for preparing compounds showing strong inhibiting activities against squalane.epoxidase of Eumycetes and strong anti-cholesterol activities. The process comprises reacting a compound of the formula: Z--CH.sub.2 --CH.dbd.CH--W [I] wherein W is a halogen atom, and Z is a leaving group, with an amine in the presence of a base, if necessary, to obtain a compound of the formula: ##STR1## then reacting an acetylene derivative to this compound in the presence of a palladium catalyst, to obtain a compound of the formula: ##STR2## and, if necessary, N-alkylating this compound.

  生产烯烃衍生物的过程，以及中间体，该中间体对制备显示强抑制Eumycetes角鲨烷环氧化酶和强抗胆固醇活性的化合物很有用。该过程包括在碱存在的情况下，将具有以下式的化合物：Z--CH.sub.2 --CH.dbd.CH--W [I]（其中W是卤素原子，Z是离去基团）与胺反应，以获得具有以下式的化合物：##STR1## 然后在钯催化剂存在下将乙炔衍生物与该化合物反应，以获得具有以下式的化合物：##STR2## 并在必要时对该化合物进行N-烷基化。
• Intermediates for producing enyne derivatives
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US05436354A1

  公开（公告）日：1995-07-25

  (E)-N-(3-Chloro-2-propenyl)-N-methyl-1naphthylenemethanamine and (E)-3-chloro-N-(3-chloro-2-propenyl)-N-methylbenzo[b]thiophene-7-methanami ne which are useful as intermediates in the production of enyne compounds which exhibit squalene epoxidase inhibiting activity and anti-Eumycetes activity.

  (E)-N-(3-氯-2-丙烯基)-N-甲基-1-萘甲胺和(E)-3-氯-N-(3-氯-2-丙烯基)-N-甲基苯并[b]噻吩-7-甲胺是在生产具有角鲨烷环氧酶抑制活性和抗真菌活性的炔烃化合物中有用的中间体。
• 5-CHLORO-2-DIFLUOROMETHOXYPHENYL PYRAZOLOPYRIMIDINE COMPOUNDS,COMPOSITIONS AND METHODS OF USE THEREOF
  申请人：Genentech, Inc.

  公开号：US20160237086A1

  公开（公告）日：2016-08-18

  Compounds of Formula (00A) and methods of use as Janus kinase inhibitors are described herein.

  本文描述了化学式(00A)的化合物以及作为Janus激酶抑制剂的使用方法。
• Process for producing enyne Derivatives
  申请人：BANYU PHARMACEUTICAL CO., LTD.

  公开号：EP0645369A2

  公开（公告）日：1995-03-29

  The invention relates to compounds of the formula wherein R11 is a hydrogen atom, a lower alkyl group, a halo lower alkyl group, a lower alkenyl group, a lower alkynyl group or a cycloalkyl group; R21 is a hydrogen atom or a group of the formula wherein each of R3, R31 and R32, which may be the same or different, is a hydrogen atom or a lower alkyl group, each of R4, R5, R41 and R51, which may be the same or different, is a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group or a lower alkoxy group, and R42 is a hydroxyl group, a halogen atom, a group of the formula B-O (wherein B is a protecting group for a hydroxyl group), a hydroxy methyl group, a formyl group, a carboxyl group, a lower alkoxy carbonyl group, a lower alkanoyl group, an amino group, a mercapto group or a group of the formula R6-X-Y-(wherein R6 is a phenyl or thienyl group which may have one or two substituents selected from the group consisting of a halogen atom, a hydroxyl group, a lower one or two substituents selected from the group consisting of a halogen atom, a hydroxyl group, a lower alkyl group, a cyano group, a lower alkoxy group and a heterocyclic group, each of X and Y, which may be the same or different, is an oxygen atom, a sulfur atom, a carbonyl group, a group of the formula -CHRa- (wherein Ra is a hydrogen atom or a lower alkyl group) or a group of the formula -NRb- (wherein Rb is a hydrogen atom or a lower alkyl group), or X and Y together form a vinylene group or an ethynylene group), provided that when either one of X and Y is an oxygen atom, a sulfur atom or a group of the formula -NRb- (wherein Rb is as defined above), the other is a carbonyl group or a group of the formula -CHRa- (wherein Ra is as defined above), and W is a halogen atom, and a process for preparing such compounds.

  本发明涉及式如下的化合物 其中 R11 是氢原子、低级烷基、卤代低级烷基、低级烯基、低级炔基或环烷基； R21 是氢原子或式中的基团 其中 R3、R31 和 R32（可以相同或不同）各自是氢原子或低级烷基，R4、R5、R41 和 R51（可以相同或不同）各自是氢原子、卤素原子、羟基、低级烷基或低级烷氧基，R42 是羟基、卤素原子、式 B-O 的基团（其中 B 是羟基的保护基）、羟甲基、甲酰基、羧基、低级烷氧基羰基、低级烷酰基、氨基、巯基或式 R6-X-Y- （其中 R6 为苯基或噻吩基，可具有一个或两个选自卤素原子、羟基、一个或两个选自卤素原子的低级取代基、羟基、低级烷基、氰基、低级烷氧基和杂环基，X 和 Y（可以相同或不同）分别是氧原子、硫原子、羰基、式 -CHRa-（其中 Ra 是氢原子或低级烷基）或式 -NRb-（其中 Rb 是氢原子或低级烷基）、或X和Y共同形成乙烯基或乙炔基），条件是当X和Y中的一个是氧原子、硫原子或式-NRb-（其中Rb如上所定义）的基团时，另一个是羰基或式-CHRa-（其中Ra如上所定义）的基团，而W是卤素原子，以及制备此类化合物的工艺。
• Srivastav, Maneesh Kumar; Rajeeva; Salahuddin, Md., Indian Journal of Heterocyclic Chemistry, 2014, vol. 24, # 2, p. 115 - 118
  作者：Srivastav, Maneesh Kumar、Rajeeva、Salahuddin, Md.、Srinivasulu、Shanta Kumar

  DOI：——

  日期：——