2-bromomethyl-3-(p-methoxybenzyloxy)prop-1-ene | 168321-28-6

• 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: 2-bromomethyl-3-(p-methoxybenzyloxy)prop-1-ene
• 英文别名: 1-[2-(Bromomethyl)prop-2-enoxymethyl]-4-methoxybenzene
• CAS: 168321-28-6
• 化学式: C₁₂H₁₅BrO₂
• 分子量: 271.154
• InChiKey: YUCFGBNFKUTOHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯硫酚 、 2-bromomethyl-3-(p-methoxybenzyloxy)prop-1-ene 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以89%的产率得到3-[(4-methoxybenzyl)oxy]-2-[(phenylthio)methyl]propene
  参考文献：
  名称：

  Zeolite β-Induced Rearrangement of Alkoxybenzyl Allyl Ethers to Aldehydes and Ketones. 5.¹ Variation of the Allylic Moiety

  摘要：

  Allylic PMB ethers rearranged in the presence of zeolite beta to form 4-arylbutanals or 5-arylpentanones depending on the substituent pattern of the allylic moiety. Best results were obtained with substrates carrying simple substituents in the allylic 2-position, but a couple of substrates lacking a 2-substituent also rearranged. More functionalized substituents in this position were not tolerated. A propargyl PMB ether and a homoallylic PMB ether rearranged as well, but the products were mixtures of isomeric olefins. The 4-arylbutanals 2c and 2e and the 5-arylpentanone 2j were cyclized in PPA to give naphthalene and dihydronaphthalene derivatives, respectively.

  DOI：

  10.1021/jo972243o
• 作为产物：
  描述：

  2-hydroxymethyl-3-(p-methoxybenzyloxy)prop-1-ene 在 咪唑 、 溴 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以85%的产率得到2-bromomethyl-3-(p-methoxybenzyloxy)prop-1-ene
  参考文献：
  名称：

  A new synthetic approach to 5-dethia-4-methyl-5-oxacephems

  摘要：

  Starting from (L)-ethyl lactate and 4-vinyloxy-azetidin-2-one the diastereomeric (4S,6R)- and (4S,6S)-4-methyl-5-oxa-3-methylene and 3-oxo-cephams were obtained. The formation of the cepham skeleton proceeds with a diastereomeric excess up to 80%, depending on catalyst and reaction conditions. For comparison, the corresponding racemic cephams lacking a methyl at C-4 or with a gem-dimethyl group at C-4 were synthesized. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00939-6

文献信息

• 3-AMINO-5-CARBOXY-SUBSTITUTED PIPERIDINES AND 3-AMINO-4-CARBOXY-SUBSTITUTED PYRROLIDINES AS TACHYKININ ANTAGONISTS
  申请人：PFIZER INC.

  公开号：EP0719253B1

  公开（公告）日：2004-04-28
• [EN] 3-AMINO-5-CARBOXY-SUBSTITUTED PIPERIDINES AND 3-AMINO-4-CARBOXY-SUBSTITUTED PYRROLIDINES AS TACHYKININ ANTAGONISTS<br/>[FR] PIPERIDINES 3-AMINO-5-CARBOXY-SUBSTITUEES ET PYRROLIDINES 3-AMINO-4-CARBOXY-SUBSTITUEES UTILISEES COMME ANTAGONISTES DE TACHYKININE
  申请人：PFIZER INC.

  公开号：WO1995007886A1

  公开（公告）日：1995-03-23

  (EN) A compound of the chemical formula (I) and its pharmaceutically acceptable salt, wherein Y is C2-C4 alkylene; Z is a valence bond or C1-C6 alkylene; R1 is substituted or unsubstituted aryl (e.g., phenyl and naphthyl) or heteroaryl (e.g., thienyl and furyl); R2 is hydrogen or C1-C6 alkyl; R3 is hydrogen, hydroxy or the like; R4 is substituted or unsubstituted benzyl or the like. Typical examples are (2S*,3S*,4S*,5R*)-4-Carboxy-3-[N-(5-Isopropyl-2-methoxy-benzyl)amino]-5-methyl-2-phenylpyrrolidine and (2S*,3S*,5S*)-5-Carboxy-3-[N-(2-methoxy-5-trifluoromethoxybenzyl)amino]-2-phenylpiperidine. The novel substituted azaheterocyclecarboxylic acids in this invention have excellent substance P antagonistic activity and are thus useful for the treatement of gastrointestinal disorders, central nervous system disorders, allergy, inflammatory diseases, asthma, pain, emesis or migraine in mammals, especially humans.(FR) Composé de formule chimique (I) et son sel acceptable en pharmacologie. Dans la formule, Y représente C2-C4 alkylène; Z représente une liaison de valence ou C1-C6 alkylène; R1 représente aryle substitué ou non (par exemple phényle et naphtyle) ou hétéroaryle (par exemple thiényle et furyle); R2 représente hydrogène ou C1-C6 alkyle; R3 représente hydrogène, hydroxy ou une substance analogue; R4 représente benzyle substitué ou non ou une substance analogue. Des exemples typiques sont la (2S*,3S*,4S*,5R*)-4-carboxy-3-[N-(5-isopropyl-2-méthoxy-benzyl)amino]-5-méthyl-2-phénylpyrrolidine et la (2S*,3S*,5S*)-5-carboxy-3-[N-(2-méthoxy-5-trifluorométhoxybenzyl)amino]-2-phénylpipéridine. Les nouveaux acides azahétérocyclecarboxyliques substitués ci-décrits présentent une excellente activité d'antagonistes vis-à-vis de la substance P et sont utiles dans le traitement de troubles gastro-intestinaux et du système nerveux central, d'allergies, de maladies inflammatoires, d'asthme, de la douleur, des vomissements, ou de la migraine chez les mammifères, notamment chez l'homme.
• Zeolite β-Induced Rearrangement of Alkoxybenzyl Allyl Ethers to Aldehydes and Ketones. 5.¹ Variation of the Allylic Moiety
  作者：Johan Wennerberg、Charlotte Olofsson、Torbjörn Frejd

  DOI：10.1021/jo972243o

  日期：1998.5.1

  Allylic PMB ethers rearranged in the presence of zeolite beta to form 4-arylbutanals or 5-arylpentanones depending on the substituent pattern of the allylic moiety. Best results were obtained with substrates carrying simple substituents in the allylic 2-position, but a couple of substrates lacking a 2-substituent also rearranged. More functionalized substituents in this position were not tolerated. A propargyl PMB ether and a homoallylic PMB ether rearranged as well, but the products were mixtures of isomeric olefins. The 4-arylbutanals 2c and 2e and the 5-arylpentanone 2j were cyclized in PPA to give naphthalene and dihydronaphthalene derivatives, respectively.
• A new synthetic approach to 5-dethia-4-methyl-5-oxacephems
  作者：Zbigniew Kałuża、Arkadiusz Kazimierski、Krzysztof Lewandowski、Kinga Suwińska、Beata Szczȩsna、Marek Chmielewski

  DOI：10.1016/s0040-4020(03)00939-6

  日期：2003.7

  Starting from (L)-ethyl lactate and 4-vinyloxy-azetidin-2-one the diastereomeric (4S,6R)- and (4S,6S)-4-methyl-5-oxa-3-methylene and 3-oxo-cephams were obtained. The formation of the cepham skeleton proceeds with a diastereomeric excess up to 80%, depending on catalyst and reaction conditions. For comparison, the corresponding racemic cephams lacking a methyl at C-4 or with a gem-dimethyl group at C-4 were synthesized. (C) 2003 Elsevier Ltd. All rights reserved.