(E)-4-(naphthalene-1-yl)-3-butenoic acid | 200999-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-4-(naphthalene-1-yl)-3-butenoic acid
• 英文别名: 4-Naphthalen-1-yl-but-3-enoic acid；(E)-4-naphthalen-1-ylbut-3-enoic acid
• CAS: 200999-20-8
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: HZKZXHHWYHPOEY-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-(naphthalene-1-yl)-3-butenoic acid 在 硫酸 、 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 、 苯 为溶剂， 反应 17.5h， 生成 methyl (E)-2-diazo-4-(1-naphthyl)-3-butenoate
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Diarylacetates and 4,4-Diarylbutanoates. A Formal Asymmetric Synthesis of (+)-Sertraline

  摘要：

  The intermolecular C-H insertion chemistry of phenyldiazoacetates catalyzed by dirhodium tetrakis((S)-N (dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOSP)(4)) can be effectively carried out on cyclohexadienes, leading to the asymmetric synthesis of diarylacetates. The reaction of vinyldiazoacetates with cyclohexadienes results in an unprecedented carbenoid reaction that is formally a combined C-H insertion/Cope rearrangement. The synthetic utility of this novel transformation was demonstrated by its utilization in a formal asymmetric synthesis of (+)-sertraline.

  DOI：

  10.1021/ol9905699
• 作为产物：
  描述：

  1-萘甲醛 、 2-(羧乙基)三苯基氯化膦 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 生成 (E)-4-(naphthalene-1-yl)-3-butenoic acid
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Diarylacetates and 4,4-Diarylbutanoates. A Formal Asymmetric Synthesis of (+)-Sertraline

  摘要：

  The intermolecular C-H insertion chemistry of phenyldiazoacetates catalyzed by dirhodium tetrakis((S)-N (dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOSP)(4)) can be effectively carried out on cyclohexadienes, leading to the asymmetric synthesis of diarylacetates. The reaction of vinyldiazoacetates with cyclohexadienes results in an unprecedented carbenoid reaction that is formally a combined C-H insertion/Cope rearrangement. The synthetic utility of this novel transformation was demonstrated by its utilization in a formal asymmetric synthesis of (+)-sertraline.

  DOI：

  10.1021/ol9905699

文献信息

• Direct Enantioselective and Regioselective Alkylation of β,γ-Unsaturated Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries
  作者：Kai Yu、Bukeyan Miao、Wenqi Wang、Armen Zakarian

  DOI：10.1021/acs.orglett.9b00587

  日期：2019.3.15

  Efficient asymmetric alkylation of β,γ-unsaturated carboxylic acids without prior functionalization is enabled by chiral lithium amides. Enantioselectivity is imparted by a putative mixed lithium amide–enediolate aggregate that acts a traceless auxiliary formed in situ, allowing for a direct asymmetric alkylation and a simple recovery of the chiral reagent.

  β，γ-不饱和羧酸的有效不对称烷基化无需事先官能化就可以通过手性锂酰胺实现。对映选择性是由假定的酰胺基-烯二醇锂混合聚集体赋予的，该聚集体发挥就地形成的无痕助剂的作用，允许直接不对称烷基化和简单回收手性试剂。
• [EN] AGENTS WITH ANTIFUNGAL ACTIVITY AND METHODS OF USE THEREOF<br/>[FR] AGENTS ANTIFONGIQUES ET LEURS PROCEDES D'UTILISATION
  申请人：UNIVERSITY OF ALBERTA

  公开号：WO1997048279A1

  公开（公告）日：1997-12-24

  (EN) An antifungal composition is disclosed comprising at least one compound selected from the group consisting of: (a) at least one compound of formula (I), and (b) at least one compound of formula (II), or an alkali or alkali earth salt thereof, and a carrier or diluent therefor. Methods of reducing or inhibiting fungal growth, fungal wood decay and fungal wood stain are also disclosed, along with a method of reducing or inhibiting fairy rings. Paints, stains, cleaning products, disinfectants and wood or lawn treatments containing the compounds are also disclosed.(FR) Composition antifongique contenant au moins un composé sélectionné dans le groupe constitué par: (a) au moins un composé représenté par la formule (I) et (b) au moins un composé représenté par la formule (II), ou un des ses sels alcalins ou terreux alcalins, ainsi qu'un véhicule et un diluant. Procédés servant à limiter ou à inhiber la croissance des champignons, la détérioration du bois et les taches sur le bois provoquées par les champignons, et procédé servant à limiter ou à empêcher les ronds de sorcière. Produits servant à nettoyer la peinture et les taches, désinfectants et produits de traitement du bois et de la pelouse contenant ces composés.
• Catalytic Asymmetric Synthesis of Diarylacetates and 4,4-Diarylbutanoates. A Formal Asymmetric Synthesis of (+)-Sertraline
  作者：Huw M. L. Davies、Douglas G. Stafford、Tore Hansen

  DOI：10.1021/ol9905699

  日期：1999.7.1

  The intermolecular C-H insertion chemistry of phenyldiazoacetates catalyzed by dirhodium tetrakis((S)-N (dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOSP)(4)) can be effectively carried out on cyclohexadienes, leading to the asymmetric synthesis of diarylacetates. The reaction of vinyldiazoacetates with cyclohexadienes results in an unprecedented carbenoid reaction that is formally a combined C-H insertion/Cope rearrangement. The synthetic utility of this novel transformation was demonstrated by its utilization in a formal asymmetric synthesis of (+)-sertraline.