2-(菲-2-基)乙酰氯 | 74681-55-3

• 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-(菲-2-基)乙酰氯
• 英文名称: 3-(N-benzyl-N-methylamino)-1-phenyl-propan-1-ol
• 英文别名: 3-[Benzyl(methyl)amino]-1-phenyl-1-propanol；3-[benzyl(methyl)amino]-1-phenylpropan-1-ol
• CAS: 74681-55-3
• 化学式: C₁₇H₂₁NO
• 分子量: 255.36
• InChiKey: HOJWFVSHZMXLAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2-(菲-2-基)乙酰氯 在 sodium hydride 、 氯甲酸甲酯 作用下， 以 N,N-二甲基乙酰胺 、 苯 为溶剂， 反应 17.0h， 生成 氟西汀
  参考文献：
  名称：

  SYNTHESIS, ANOREXIGENIC ACTIVITY AND QSAR OF SUBSTITUTED ARYLOXYPROPANOLAMINES

  摘要：

  Substituted aryloxypropanolamines (6-20) were synthesized and evaluated for their anorexigenic activity. Among them 4-cyanoaryloxy (7), 2-methylaryloxy (9), 2-methoxyl aryloxy (10), 4-acetamidoaryloxy (15), 4-bromoaryloxy (16) and 4-ethylaminoaryloxy (20) exhibited potent anorexigenic activity. According to QSAR studies, the electronic parameter 'sigma' plays an important role in describing the variance in activity.

  DOI：

  10.1007/s00044-004-0107-6
• 作为产物：
  描述：

  (2RS,6SR)-2,6-diphenyl-[1,3]oxazinan-4-one 在 lithium aluminium tetrahydride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 2-(菲-2-基)乙酰氯
  参考文献：
  名称：

  5-Phenylthio-1,3-oxazinan-4-ones via hetero Diels–Alder reactions: synthesis of (R)- and (S)-Duloxetines and Fluoxetines

  摘要：

  The synthesis of 5-phenylthio-1,3-oxazinan-4-ones, through a hetero Diels-Alder strategy, is described. The cycloadducts thus prepared have been shown to be useful intermediates for the synthesis of 1,3-aminoalcohols, valuable intermediates in the preparation of biologically significant molecules, e.g., optically active Duloxetines and Fluoxetines. In the course of this elaboration a novel microwave assisted desulfurization reaction is reported. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.006

文献信息

• Manganese-Catalyzed Anti-Markovnikov Hydroamination of Allyl Alcohols via Hydrogen-Borrowing Catalysis
  作者：Kuhali Das、Koushik Sarkar、Biplab Maji

  DOI：10.1021/acscatal.1c01199

  日期：2021.6.18

  In this article, a selective formal anti-Markovnikov hydroamination of allyl alcohols is presented. It enables the versatile synthesis of valuable γ-amino alcohol building blocks. A phosphine-free Earth’s abundant manganese(I) complex catalyzed the reaction under hydrogen-borrowing conditions. A vast range of aliphatic, aromatic amines, drug molecules, and natural product derivatives underwent successful

  控制加氢胺化反应的选择性对于胺的多样化来说是一项极具挑战性但非常理想的任务。在本文中，介绍了烯丙醇的选择性正式反马尔科夫尼科夫加氢胺化。它使有价值的 γ-氨基醇构建块的多功能合成成为可能。一种不含磷的地球上丰富的锰 (I) 配合物在借氢条件下催化了该反应。大量的脂肪族、芳香族胺、药物分子和天然产物衍生物与具有优异官能团耐受性的伯烯和仲烯丙醇成功加氢胺化（57 个例子）。该催化可以在克级进行，并已应用于药物分子的合成。
• [EN] PROPANAMINE DERIVATIVES AS SEROTONIN AND NOREPINEPHRINE REUPTAKE INHIBITORS<br/>[FR] DERIVES DE PROPANAMINE UTILISES EN TANT QU'INIHIBITEURS DU RECAPTAGE DE LA SEROTONINE ET DE LA NOREPINEPHRINE
  申请人：LILLY CO ELI

  公开号：WO2004043931A1

  公开（公告）日：2004-05-27

  There is provided a heretoaryloxy/thio 3-substituted propanamine compound of formula (I) wherein A is selected from -O- and -S-; X is selected from phenyl optionally substituted with up to 5 substituents each independently selected from halo, C1-C4 alkyl and C1-C4 alkoxy, thienyl optionally substituted with up to 3 substituents each independently selected from halo and C1-C4 alkyl, and C2-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl and C4-C8 cycloalkylalkyl, each of which may be optionally substituted with up to 3 substituents each independently selected from halo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)n- where n is 0, 1 or 2, -CF3, -CN and -CONH2; Y is selected from dihydrobenzothienyl, benzothiazolyl, benzoisothiazolyl, quinolyl, isoquinolyl, naphthyridyl, and thienopyridyl, each of which may be optionally substituted with up to 4 or, where possible, up to 5 substituents each independently selected from halo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)n- where n is 0, 1 or 2, nitro, acetyl, -CF3, -SCF3 and cyano; Z is selected from H, OR3 or F, wherein R3 is selected from H, C1-C6 alkyl and phenyl C1-C6 alkyl; R1 and R2 are each independently H or C1-C4 alkyl; and pharmaceutically acceptable salts thereof.

  提供了一种公式（I）的醚/硫代3-取代丙胺化合物，其中A选自-O-和-S-；X选自苯基，可选地取代为最多5个取代基，每个取代基独立选自卤素、C1-C4烷基和C1-C4烷氧基，噻吩基，可选地取代为最多3个取代基，每个取代基独立选自卤素和C1-C4烷基，以及C2-C8烷基，C2-C8烯基，C3-C8环烷基和C4-C8环烷基烷基，每个基可选地取代为最多3个取代基，每个取代基独立选自卤素、C1-C4烷基、C1-C4烷氧基、C1-C4烷基-S(O)n-其中n为0、1或2、-CF3、-CN和-CONH2；Y选自二氢苯并噻吩基，苯并噻唑基，苯并异噻唑基，喹啉基，异喹啉基，萘啉基和噻吩吡啉基，每个基可选地取代为最多4个或在可能的情况下，最多5个取代基，每个取代基独立选自卤素、C1-C4烷基、C1-C4烷氧基、C1-C4烷基-S(O)n-其中n为0、1或2、硝基、乙酰基、-CF3、-SCF3和氰基；Z选自H、OR3或F，其中R3选自H、C1-C6烷基和苯基C1-C6烷基；R1和R2各自独立地为H或C1-C4烷基；以及其药学上可接受的盐。
• N-substituted derivatives of
  申请人：PLIVA Farmaceutska kemijska, Prehrambena i kozmeticka industrija,

  公开号：US05618968A1

  公开（公告）日：1997-04-08

  The invention provides the preparation procedure for N-substituted derivatives of N-methyl-3-(p-trifluoromethylphenoxy)-3 -phenylpropylamine having the general formula (I), where R is hydrogen and the group of the general formula (II), in which R.sub.1 is aryl, alkylaryl and alkyl group with C.sub.1 to C.sub.4 atoms, and n is 0 and 1, and also covers the compounds of the general formula (I), where R is the group of the formula (II), in which R.sub.1 is aryl and alkylaryl group, and n is 0 and 1. According to this invention by condensation of N-substituted derivatives of N-methyl-3-phenyl-3-hydroxypropylamine (XV), where R.sub.1 is benzyl and p-nitrobenzyl group and n is 0, and p-trifluoromethylchlorbenzene (XVI) prepared N-substituted derivatives of N-methyl-3-(p-trifluoromethylphenoxy)-3 -phenylpropylamine (I), where R is the group of the formula (II), in which n and R are the same as in the compound (XV), which by the reaction with chloroformic acid esther (XVII), where R.sub.1 aryl, alkylaryl and alkyl group with C.sub.1 to C.sub.4 atoms, are converted to N-substituted derivatives of N-methyl-3-(p -trifluoromethylphenoxy)-3-phenylpropylamine (I), where R is the group of the formula (II), in which R.sub.1 is the same as in the compound (XVII), and n is 1, from which is prepared the compound of the formula (I), in which R is hydrogen (Fluoxetin), by basic hydrolysis and/or catalytic hydrogenolysis, when R is the group of the formula (II), in which R.sub.1 is benzyl and p-nitrobenzyl group, and n is 0 and 1.

  本发明提供了N-取代N-甲基-3-(对三氟甲基苯氧基)-3-苯基丙胺的制备方法，其具有通式(I)，其中R为氢原子和通式(II)中的基团，其中R1为芳基、烷基芳基和碳原子数为C1到C4的烷基，n为0和1，并且还包括通式(I)的化合物，其中R为通式(II)中的基团，其中R1为芳基和烷基芳基基团，n为0和1。根据本发明，通过N-取代N-甲基-3-苯基-3-羟基丙胺(XV)和p-三氟甲基氯苯(XVI)的缩合反应，制备了N-取代N-甲基-3-(对三氟甲基苯氧基)-3-苯基丙胺(I)，其中R为通式(II)中的基团，其中n和R与化合物(XV)中相同，通过与氯甲酸酯(XVII)反应，其中R1为芳基、烷基芳基和碳原子数为C1到C4的烷基，转化为N-取代N-甲基-3-(对三氟甲基苯氧基)-3-苯基丙胺(I)，其中R为通式(II)中的基团，其中R1与化合物(XVII)中相同且n为1，从而通过碱性水解和/或催化氢解制备出通式(I)中R为氢原子(Fluoxetin)的化合物，当R为通式(II)中的基团，其中R1为芳基和p-硝基苯基基团，n为0和1。
• [EN] PROCESS FOR THE PREPARATION OF FLUOXETINE<br/>[FR] PROCEDE PREPARATION DE FLUOXETINE
  申请人：EGIS GYÓGYSZERGYÁR RT.

  公开号：WO1998011054A1

  公开（公告）日：1998-03-19

  (EN) The invention relates to a process for the preparation of N-methyl-[3-phenyl-3-[4-(trifluoromethyl)-phenoxy]-propyl]-amine of the Formula (I) and pharmaceutically acceptable acid addition salts thereof by reaction of N,N-dimethyl-3-phenyl-3-[4-(trifluoromethyl)-phenoxy]-propyl}-amine of the Formula (III) and ethyl chloro formate and hydrolysis and decarboxylation of the N-methyl-N-ethoxycarbonyl-3-phenyl-3-[4-(trifluoromethyl)-phenoxy]-propyl}-amine of the Formula (II) and if desired salt formation which comprises carrying out the reaction of the compound of the Formula (III) and ethyl chloro formate in toluene or xylene or a mixture thereof at a temperature below 90 °C; removing the contaminations and by-products from the reaction mixture by treatment with a diluted acid; separating the organic phase which contains the urethane derivative of the Formula (II) and reacting said organic phase, without isolating the urethane derivative of the Formula (II), with an alkali hydroxide at the boiling point of the reaction mixture in the presence of water and optionally n-butanol; removing the inorganic compounds; and if desired converting the base of the Formula (I) thus obtained into a pharmaceutically acceptable acid addition salt thereof. The compounds of the Formula (I) are a known valuable antidepressant.(FR) L'invention concerne un procédé de préparation de N-méthyl-[3-phényl-3[4-(trifluorométhyl)-phénoxy]-propyl]-amine de formule (I) et des sels d'addition d'acide de celle-ci, acceptables sur le plan pharmaceutique. Ledit procédé consiste à faire réagir du N,N-diméthyl-3-phényl-3-[4-(trifluorométhyl)-phénoxy]-propyl}-amine de formule (III) et du chloroformiate d'éthyle et à hydrolyser et décarboxyler le N-méthyl-N-éthoxycarbonyl-3-phényl-3[4-(trifluorométhyl)-phénoxy]-propyl}-amine de formule (II), et si besoin est, à former un sel par la mise en réaction du composé de formule (III) et de chloroformiate d'éthyle dans du toluène, du xylène ou un mélange des deux, à une température inférieure à 90 °C; à enlever les contaminants et les sous-produits du mélange réactionnel par traitement au moyen d'un acide dilué; à séparer la phase organique qui contient un dérivé uréthane de formule (II) et à la faire réagir, sans que le dérivé uréthane de formule (II) soit isolé, avec un hydroxyde alcalin, au point d'ébullition du mélange réactionnel, en présence d'eau et éventuellement de n-butanol; à enlever les composés inorganiques; et si, besoin est, à transformer la base de formule (I) ainsi obtenue en un sel d'addition d'acide de celle-ci, acceptable sur le plan pharmaceutique. Les composés de formule (I) sont des antidépresseurs connus efficaces.

  本发明涉及一种制备公式(I)的N-甲基-[3-苯基-3-[4-(三氟甲基)苯氧基]-丙基]-胺及其药学上可接受的酸盐的方法，该方法通过将公式(III)的N，N-二甲基-3-苯基-3-[4-(三氟甲基)苯氧基]-丙基}-胺与氯乙酸乙酯反应，并水解和脱羧公式(II)的N-甲基-N-乙氧羰基-3-苯基-3-[4-(三氟甲基)苯氧基]-丙基}-胺，并如有需要形成盐，包括在甲苯或二甲苯或二者的混合物中以低于90℃的温度进行公式(III)的化合物和氯乙酸乙酯的反应；通过用稀酸处理反应混合物中的污染物和副产物来去除它们；分离含有公式(II)的脲醇衍生物的有机相，并在存在水和必要时n-丁醇的情况下，在反应混合物的沸点处与碱性氢氧化物反应，而不分离公式(II)的脲醇衍生物；去除无机化合物；如有需要，将得到的公式(I)的碱转化为药学上可接受的酸盐。公式(I)的化合物是一种已知的有价值的抗抑郁药物。
• [EN] HETEROARYLOXY 3-SUBSTITUTED PROPANAMINES S SEROTONIN AND NOREPINEPHRINE REUPTAKE INHIBITORS<br/>[FR] PROPANAMINES SUBSTITUEES EN 3 PAR UN HETEROARYLOXY UTILISEES EN TANT QU'INHIBITEURS DE RECAPTAGE DE SEROTONINE ET DE NOREPINEPHRINE
  申请人：LILLY CO ELI

  公开号：WO2002094262A1

  公开（公告）日：2002-11-28

  There is provided a heretoaryloxy 3-substituted propanamine compound of formula (I): wherein A is selected from -O- and -S-; X is selected from phenyl optionally substituted with up to 5 substituents selected from halo, C1-C4 alkyl and C1-C4 alkoxy, and thienyl optionally substituted with up to 3 substituents selected from halo and C1-C4 alkyl; Y is selected from benzothienyl, indolyl and benzofuranyl, optionally substituted with up to 5 substituents selected from halo, C1-C4 alkyl, C1-C4 alkoxy, nitro, acetyl and cyano; and when Y is indolyl it may be substituted or further substituted by an N-substituent selected from C1-C4 alkyl; R1 and R2 are each independently H or C1-C4 alkyl; and pharmaceutically acceptable salts thereof.

  提供了一种公式（I）的取代了3-丙胺基的芳氧基化化合物，其中A选自-O-和-S-; X选自苯基，可选地取代高达5个卤素、C1-C4烷基和C1-C4烷氧基，以及噻吩基，可选地取代高达3个卤素和C1-C4烷基; Y选自苯并噻吩基、吲哚基和苯并呋喃基，可选地取代高达5个卤素、C1-C4烷基、C1-C4烷氧基、硝基、乙酰基和氰基; 当Y为吲哚基时，它可以被C1-C4烷基的N取代或进一步取代; R1和R2各自独立地为H或C1-C4烷基;以及其药学上可接受的盐。