(E)-4-(benzylamino)but-3-en-2-one | 187606-80-0

• 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: (E)-4-(benzylamino)but-3-en-2-one
• 英文别名: 4-(benzylamino)but-3-en-2-one；1-Buten-3-one, 1-(benzylamino)-
• CAS: 187606-80-0
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: CQWWYPKMJPSBJK-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-(benzylamino)but-3-en-2-one 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(III) hexafluoroantimonate 、 potassium carbonate 、 戴斯-马丁氧化剂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 6.78h， 生成 (1R,4R,9S)-methyl-3-benzyl-13-oxo-3-azatricyclotridec[8.3.1.0(4,9)]-5-ene-1-carboxylate
  参考文献：
  名称：

  The enantioselective synthesis of tetracyclic methyllycaconitine analogues

  摘要：

  A new enantioselective synthesis of ABEF ring analogues of methyllycaconitine has been developed using a chiral cobalt(III) salen-catalyzed Diels-Alder reaction to form the B ring. Subsequent elaboration to form the A, E and F rings was achieved by sequential Dieckmann, Mannich and Wacker-type cyclizations to afford tetracyclic analogues in 97.5% ee. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.026
• 作为产物：
  描述：

  反式-4-甲氧基-3-丁烯-2-酮 、 苄胺 在 scandium(III) triflate 作用下， 以 氘代氯仿 为溶剂， 反应 24.0h， 生成 (E)-4-(benzylamino)but-3-en-2-one
  参考文献：
  名称：

  A multicomponent formal [1+2+1+2]-cycloaddition for the synthesis of dihydropyridines

  摘要：

  在路易斯酸催化条件下，甲氧基乙烯基甲基酮与不同胺和醛的反应，产生了一种新颖的、正式的、逐步的[1+2+1+2]环加成，从而得到二氢吡啶产品。

  DOI：

  10.1039/c2cc31495a

文献信息

• [EN] OXIDISABLE PYRIDINE DERIVATIVES, THEIR PREPARATION AND USE AS ANTI-ALZHEIMER AGENTS<br/>[FR] DÉRIVÉS DE PYRIDINE OXYDABLE, LEUR PRÉPARATION ET LEUR UTILISATION EN TANT QU'AGENTS ANTI ALZHEIMER
  申请人：INSA INST NAT DES SCIENCES APPLIQUÉES DE ROUEN

  公开号：WO2014114742A1

  公开（公告）日：2014-07-31

  A compound of formula (I) in which the dotted lines indicate the presence of at least one double bond; n = 0 to 4; R3 and R4 are H, or when n = 1, R3 and R4 can also form together a double bond between the carbon atoms, and m = 0, 1 or 2, Z is CH or N or Z is C and - CHR3- is =CH- linked by the double bond to cyclopentanone; or - (-)m- is absent, and Z is NH, >N-alkyl, >N-phenyl, >N-benzyl or >N heteroaryl; R8 is alkyl, aryl or heteroaryl which can be optionally substituted; EWG represents an electron withdrawing group selected from the group comprising COOR, COSR, CONRR', CN, COR, CF3, SOR, SO2R, SONRR', SO2NRR', NO2, halogen, heteroaryl; and the pharmaceutical salts and stereisomers thereof. The compounds of formula (I) are potent in the treatment of neurodegenerative diseases such as Alzheimer's disease.

  式（I）的化合物，其中虚线表示至少存在一条双键；n = 0至4；R3和R4为H，或当n = 1时，R3和R4也可以共同形成碳原子之间的双键，m = 0、1或2，Z为CH或N，或Z为C且-CHR3-为=CH-通过双键连接到环戊酮；或-（-）m-不存在，Z为NH，>N-烷基，>N-苯基，>N-苄基或> N杂环烷基；R8为烷基、芳基或杂环烷基，可以选择性地被取代；EWG代表从包括COOR、COSR、CONRR'、CN、COR、CF3、SOR、SO2R、SONRR'、SO2NRR'、NO2、卤素、杂环烷基在内的电子吸引基团；以及其药用盐和立体异构体。式（I）的化合物在治疗诸如阿尔茨海默病等神经退行性疾病方面具有很强的作用。
• Oxidisable pyridine derivatives, their preparation and use as anti-Alzheimer agents
  申请人：INSA (Institut National des Sciences Appliquees) de Rouen

  公开号：EP2759536A1

  公开（公告）日：2014-07-30

  A compound of the formula (I) in which the dotted lines indicate the presence of at least one double bond; n = 0 to 4; R3 and R4 are H, or when n = 1, R3 and R4 can also form together a double bond between the carbon atoms, and m = 0, 1 or 2, Z is CH or N or Z is C and -CHR3- is =CH- linked by the double bond to the cyclopentanone; or -(-)m- is absent, and Z is NH, >N-alkyl, >N-phenyl, >N-benzyl or >N-heteroaryl; R8 is alkyl, aryl or heteroaryl which can be optionally substituted; EWG represents an electron withdrawing group selected from the group comprising COOR, COSR, CONRR', CN, COR, CF3, SOR, SO2R, SONRR', SO2NRR', NO2, halogen, heteroaryl; and the pharmaceutical salts or tautomers thereof. The compounds of formula (I) are potent in the treatment of neurodegenerative diseases such as Alzheimer's disease.

  式(I)的化合物，其中虚线表示至少存在一个双键；n = 0到4；R3和R4为H，或当n = 1时，R3和R4也可以一起形成碳原子之间的双键，m = 0、1或2，Z为CH或N，或Z为C且-CHR3-为=CH-，通过双键与环戊酮相连；或-(-)m-不存在，Z为NH，>N-烷基，>N-苯基，>N-苄基或>N-杂环烷基；R8为烷基、芳基或杂环烷基，可选择性地取代；EWG代表从COOR、COSR、CONRR'、CN、COR、CF3、SOR、SO2R、SONRR'、SO2NRR'、NO2、卤素、杂环烷基组成的电子吸引基团；以及其药用盐或互变异构体。式(I)的化合物在治疗像阿尔茨海默病这样的神经退行性疾病中具有很强的作用。
• OXIDISABLE PYRIDINE DERIVATIVES, THEIR PREPARATION AND USE AS ANTI-ALZHEIMER AGENTS
  申请人：INSA (INSTITUT NATIONAL DES SCIENNCES APPLIQUÉES) DE ROUEN

  公开号：US20150353493A1

  公开（公告）日：2015-12-10

  A compound of formula (I) in which the dotted lines indicate the presence of at least one double bond; n=0 to 4; R 3 and R 4 are H, or when n=1, R 3 and R 4 can also form together a double bond between the carbon atoms, and m=0, 1 or 2, Z is CH or N or Z is C and —CHR 3 — is ═CH— linked by the double bond to cyclopentanone; or −(−) m - is absent, and Z is NH, >N-alkyl, >N-phenyl, >N-benzyl or >N heteroaryl; R 8 is alkyl, aryl or heteroaryl which can be optionally substituted; EWG represents an electron withdrawing group selected from the group comprising COOR, COSR, CONRR′, CN, COR, CF 3 , SOR, SO 2 R, SONRR′, SO 2 NRR′, NO 2 , halogen, heteroaryl; and the pharmaceutical salts and stereisomers thereof. The compounds of formula (I) are potent in the treatment of neurodegenerative diseases such as Alzheimer's disease.

  式(I)的化合物中，虚线表示存在至少一个双键；n = 0至4；R3和R4为H，或当n = 1时，R3和R4也可以共同形成碳原子之间的双键，m = 0、1或2，Z为CH或N，或者Z为C，-CHR3-与环戊酮通过双键连接，或-(-)m-不存在，Z为NH，>N-烷基，>N-苯基，>N-苯甲基或> N杂环芳基；R8为烷基、芳基或杂环芳基，可以选择性地被取代；EWG代表从COOR、COSR、CONRR'、CN、COR、CF3、SOR、SO2R、SONRR'、SO2NRR'、NO2、卤素、杂环芳基中选择的电子吸引基；以及其药物盐和立体异构体。式(I)的化合物在治疗神经退行性疾病，如阿尔茨海默病方面具有很强的疗效。
• Processes for preparing medicaments for the treatment of cardiovascular diseases and intermediates for use therein
  申请人：Bial-Portela & CA., S.A.

  公开号：US10329268B2

  公开（公告）日：2019-06-25

  The present invention provides a compound of formula N wherein: X is CH2, oxygen or sulphur; R1, R2 and R3 are the same or different and signify hydrogens, halogens, alkyl, alkyloxy, hydroxy, nitro, alkylcarbonylamino, alkylamino or dialkylamino group, wherein N is in the form of the individual R- and S-enantiomer or a mixture of the (R)- and (S)-enantiomer. The present invention also provides a compound of formula MA. The present invention also provides processes for preparing the above compounds, and processes involving their use. The compounds are particularly useful as intermediates in the synthesis of peripherally-selective inhibitors of dopamine-β-hydroxylase.

  本发明提供了一种式 N 的化合物，其中：X为CH2、氧或硫；R1、R2和R3相同或不同，表示氢、卤素、烷基、烷氧基、羟基、硝基、烷基羰基氨基、烷基氨基或二烷基氨基，其中N为单独的R-和S-对映体或(R)-和(S)-对映体的混合物形式。本发明还提供了式 MA 的化合物。本发明还提供了制备上述化合物的工艺以及涉及其使用的工艺。这些化合物作为合成多巴胺-β-羟化酶外周选择性抑制剂的中间体特别有用。
• Microwave-Assisted Palladium-Catalyzed Allylation of β-Enaminones
  作者：Julie Oble、Giovanni Poli、Imen Erray、Farhat Rezgui

  DOI：10.1055/s-0034-1378540

  日期：——

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