4-(N-Methyl-anilinomethyl)-phenol | 82965-58-0

• 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: 4-(N-Methyl-anilinomethyl)-phenol
• 英文别名: 4-[(N-methylanilino)methyl]phenol
• CAS: 82965-58-0
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: ILBJNQKYQYLTAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-硝基-2-糠酰氯 、 4-(N-Methyl-anilinomethyl)-phenol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 [4-[(N-methylanilino)methyl]phenyl] 5-nitrofuran-2-carboxylate
  参考文献：
  名称：

  Structural Modulation Study of Inhibitory Compounds for Ribonuclease H Activity of Human Immunodeficiency Virus Type 1 Reverse Transcriptase

  摘要：

  人类免疫缺陷病毒 1 型（HIV-1）的逆转录酶具有两种酶功能。其中一个功能是核糖核酸酶（RNase）H 活性，它只消化 RNA/DNA 混合体中的 RNA。RNase H 活性是一类新型抗艾滋病毒药物的诱人靶点，因为目前还没有获得批准的抑制剂。在我们以前的研究中，通过化学筛选发现了一种以 5-硝基呋喃-2-羧酸酯为核心的药剂，并合成了数十种衍生物以提高化合物的效力。在这项工作中，我们对部分化学结构进行了调整，以加深对类似化合物结构-活性关系的理解。研究表明，几种具有硝基呋喃-苯基酯骨架的衍生物是有效的 RNase H 抑制剂。在苯基环上连接甲氧基羰基和甲氧基基团可提高抑制效力。这些活性衍生物没有观察到明显的细胞毒性。相比之下，具有硝基呋喃-苄酯骨架的衍生物无论在苄基环上连接何种官能团，都显示出适度的抑制活性。对 5-硝基-呋喃-2-羧基的调节和酯连接的转换都会导致抑制效力的急剧下降。这些发现对设计有效的 HIV-1 RNase H 酶活性抑制剂具有参考价值。

  DOI：

  10.1248/cpb.60.764

文献信息

• Process for preparing a piperidine derivative
  申请人：Sumika Fine Chemicals Co., Ltd.

  公开号：US20030144519A1

  公开（公告）日：2003-07-31

  A piperidine derivative, which can be used as an intermediate for pharmaceuticals such as paroxetine useful as antidepressants, represented by the general formula (I): 1 wherein R 1 is hydrogen atom, benzyloxycarbonyl group or tert-butoxycarbonyl group; R 2 is hydroxymethyl group, an alkylsulfonyloxymethyl group having an alkyl moiety of 1 to 2 carbon atoms, phenylsulfonyloxymethyl group which may have methyl group at the 4-position, (3,4-methylenedioxyphenyl)oxymethyl group, carboxyl group or —CO 2 R 7 group in which R 7 is an alkyl group having 1 to 5 carbon atoms, and Z is methylene group or carbonyl group, with proviso that, (A) when R 1 is benzyloxycarbonyl group or tert-butoxycarbonyl group, then R 2 is hydroxymethyl group, an alkylsulfonyloxymethyl group having an alkyl moiety of 1 to 2 carbon atoms, phenylsulfonyloxymethyl group which may have methyl group at the 4-position or (3,4-methylenedioxyphenyl)oxymethyl group, and Z is methylene group; or (B) when R 1 is hydrogen atom and Z is carbonyl group, then R 2 is carboxyl group or —CO 2 R 7 group (R 7 is as defined above); or (C) when R 1 is hydrogen atom and Z is methylene group, then R 2 is hydroxymethyl group

  一种哌啶衍生物，可用作如帕罗西汀等抗抑郁药物的中间体，由通式（I）表示：其中R1为氢原子，苄氧羰基基团或叔丁氧羰基基团；R2为羟甲基基团，具有1至2个碳原子的烷基磺酰氧甲基基团，可能在4位具有甲基基团的苯基磺酰氧甲基基团，（3,4-亚甲二氧基苯基）氧甲基基团，羧基或CO2R7基团，其中R7为具有1至5个碳原子的烷基基团，Z为亚甲基或羰基基团，但有附加条件，即（A）当R1为苄氧羰基基团或叔丁氧羰基基团时，R2为羟甲基基团，具有1至2个碳原子的烷基磺酰氧甲基基团，可能在4位具有甲基基团的苯基磺酰氧甲基基团或（3,4-亚甲二氧基苯基）氧甲基基团，而Z为亚甲基；或（B）当R1为氢原子且Z为羰基基团时，R2为羧基或CO2R7基团（其中R7如上所定义）；或（C）当R1为氢原子且Z为亚甲基时，R2为羟甲基基团。
• Piperidine derivative as intermediates for the preparation of paroxetine and process for their preparation
  申请人：SUMIKA FINE CHEMICALS Co., Ltd.

  公开号：EP0812827A1

  公开（公告）日：1997-12-17

  A piperidine derivative, which can be used as an intermediate for pharmaceuticals such as paroxetine useful as antidepressants, represented by the general formula (I): wherein R1 is hydrogen atom, benzyloxycarbonyl group or tert-butoxycarbonyl group; R2 is hydroxymethyl group, an alkylsulfonyloxymethyl group having an alkyl moiety of 1 to 2 carbon atoms, phenylsulfonyloxymethyl group which may have methyl group at the 4-position, (3,4-methylenedioxyphenyl)oxymethyl group, carboxyl group or -CO2R7 group in which R7 is an alkyl group having 1 to 5 carbon atoms, and Z is methylene group or carbonyl group, with proviso that, (A) when R1 is benzyloxycarbonyl group or tert-butoxycarbonyl group, then R2 is hydroxymethyl group, an alkylsulfonyloxymethyl group having an alkyl moiety of 1 to 2 carbon atoms, phenylsulfonyloxymethyl group which may have methyl group at the 4-position or (3,4-methylenedioxyphenyl)oxymethyl group, and Z is methylene group; or (B) when R1 is hydrogen atom and Z is carbonyl group, then R2 is carboxyl group or -CO2R7 group (R7 is as defined above); or (C) when R1 is hydrogen atom and Z is methylene group, then R2 is hydroxymethyl group. Also processes for the production of the intermediates are described.

  一种哌啶衍生物，可用作抗抑郁药帕罗西汀等药物的中间体，由通式(I)表示： 其中 R1 为氢原子、苄氧羰基或叔丁氧羰基；R2 是羟甲基、具有 1 至 2 个碳原子的烷基的烷磺酰氧基甲基、可在 4 位上具有甲基的苯磺酰氧基甲基、（3,4-亚甲基二氧苯基）氧基甲基、羧基或-CO2R7 基（其中 R7 是具有 1 至 5 个碳原子的烷基），Z 是亚甲基或羰基、但 (A) 当 R1 为苄氧羰基或叔丁氧羰基时，则 R2 为羟甲基、具有 1 至 2 个碳原子的烷基的烷基磺酰氧甲基、在 4 位可能具有甲基的苯基磺酰氧甲基或（3,4-亚甲基二氧苯基）氧甲基，且 Z 为亚甲基；或 (B) 当 R1 为氢原子且 Z 为羰基时，则 R2 为羧基或-CO2R7 基团（R7 如上定义）；或 (C) 当 R1 为氢原子且 Z 为亚甲基时，则 R2 为羟甲基。 此外，还介绍了中间体的生产工艺。
• Optical resolution of a piperidine derivative
  申请人：SUMIKA FINE CHEMICALS Co., Ltd.

  公开号：EP1384711A1

  公开（公告）日：2004-01-28

  The present invention relates to a method for preparing (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidine represented by the formula (II): The method comprises the step of optically resolving (3SR,4RS)-trans-4-(4-fluorophenyl)-3-hydroxymethylpiperidine with o-chlorotartranilic acid as an optically active organic acid.

  本发明涉及一种制备式(II)代表的(3S,4R)-反式-4-(4-氟苯基)-3-羟甲基哌啶的方法： 该方法包括以下步骤：用邻氯酒石酸作为光学活性有机酸对(3SR,4RS)-反式-4-(4-氟苯基)-3-羟甲基哌啶进行光学解析。
• Process for drying paroxetine hydrochloride
  申请人：SUMIKA FINE CHEMICALS Co., Ltd.

  公开号：EP1384720A1

  公开（公告）日：2004-01-28

  The present invention relates to a method for drying paroxetine hydrochloride containing 8 to 15% by weight of isopropanol. The method comprises the steps of: (1) drying crystals of paroxetine hydrochloride containing 8 to 15% by weight of isopropanol obtained by the precipitation of crystals of paroxetine hydrochloride from an isopropanol solution of paroxetine hydrochloride, under reduced pressure at 70°C, and (2) drying the resulting paroxetine hydrochloride under a reduced pressure at a temperature of from 80° to 110°C to give paroxetine hydrochloride having an isopropanol content of 0.1 to 5% by weight.

  本发明涉及一种干燥盐酸帕罗西汀的方法，其中含有 8%至 15%（按重量计）的异丙醇。该方法包括以下步骤 (1) 在 70°C 的减压条件下，通过从盐酸帕罗西汀的异丙醇溶液中析出盐酸帕罗西汀结晶而得到的含 8 至 15%（重量）异丙醇的盐酸帕罗西汀结晶的干燥，以及 (2) 在 80° 至 110°C 的温度下减压干燥所得的盐酸帕罗西汀，得到异丙醇含量为 0.1%至 5%（按重量计）的盐酸帕罗西汀。
• Process for preparing crystalline paroxetin hydrochloride
  申请人：SUMIKA FINE CHEMICALS Co., Ltd.

  公开号：EP1394160A1

  公开（公告）日：2004-03-03

  The present invention relates to a method for obtaining crystals of paroxetine hydrochloride containing isopropanol. The method comprises the step of adding seed crystals of paroxetine hydrochloride containing isopropanol to an isopropanol solution of paroxetine hydrochloride, preferably at a temperature of from 45° to 50°C, to afford crystalline paroxetine hydrochloride.

  本发明涉及一种获得含异丙醇的盐酸帕罗西汀晶体的方法。该方法包括以下步骤：将含有异丙醇的盐酸帕罗西汀籽晶加入盐酸帕罗西汀的异丙醇溶液中，最好在 45° 至 50°C 的温度下进行，以获得盐酸帕罗西汀晶体。