(E)-ethyl 4-(1-formyl-2-naphthoxy)but-2-enoate | 96601-25-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-ethyl 4-(1-formyl-2-naphthoxy)but-2-enoate
• 英文别名: ethyl 4-(1-formyl-2-naphthoxy)-but-2-enoate；ethyl (E)-4-(1-formylnaphthalen-2-yl)oxybut-2-enoate
• CAS: 96601-25-1
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: YAJGCAFYSNDTHN-VMPITWQZSA-N

物化性质

• 沸点：
  470.3±30.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 4-(1-formyl-2-naphthoxy)but-2-enoate 在 盐酸肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Reactions of aldehydes with hydrazine hydrochlorides in the presence of dipolarophiles: intra- and intermolecular [3+ + 2] cycloadditions

  摘要：

  DOI：

  10.1021/jo00387a031
• 作为产物：
  描述：

  4-溴巴豆酸乙酯 、 2-羟基-1-萘甲醛 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到(E)-ethyl 4-(1-formyl-2-naphthoxy)but-2-enoate
  参考文献：
  名称：

  Solid-Phase Synthesis:  Intramolecular Azomethine Ylide Cycloaddition (→Proline) and Carbanilide Cyclization (→Hydantoin) Reactions

  摘要：

  An efficient, diastereoselective route to 2,5,6,7-tetrasubstituted-1H-pyrrolo[1,2-c]imidazoles has been developed using solid-phase intramolecular azomethine ylide cycloaddition and carbanilide cyclization chemistries. To successfully execute this eight-step protocol in the solid phase, it was necessary to insert a spacer moiety between the resin and glycinate functional group. Experiments addressing the stereoselectivity of the 1,3-dipolar cycloaddition step as well as the cyclative release step are also presented.

  DOI：

  10.1021/jo9800210

文献信息

• Phosphonite mediated 1,3-dipolar cycloaddition: a route to polycyclic 2-pyrrolines from imines, acid chlorides and alkenes
  作者：Marie S. T. Morin、Sara Aly、Bruce A. Arndtsen

  DOI：10.1039/c2cc38274a

  日期：——

  2-Pyrrolines can be generated by the PhP(2-catechyl) mediated coupling of alkene-tethered imines and acid chlorides. This reaction proceeds via phosphorus-containing 1,3-dipoles, which undergo cycloaddition with alkenes with high stereo- and regioselectivity. The modularity of this reaction can be used to assemble a range of polysubstituted pyrrolines in one pot transformations.

  2-吡咯啉可以通过PhP(2-儿茶酚)介导的烯烃连接的亚胺和酸氯化物的偶联反应生成。该反应通过含磷的1,3-偶极体进行，这些偶极体与烯烃发生环加成反应，具有高的立体选择性和区域选择性。这种反应的模块化特性可用于在一个反应皿中组装一系列多取代的吡咯啉。
• A Facile Entry into Benzo-/Naphtho-pyrano-indolizino-indole through Sequential Intramolecular 1,3-Dipolar Cycloaddition and Pictet-Spengler Cyclisation
  作者：Raghavachary Raghunathan、G. Subramaniyan、Jayadevan Jayashankaran、Rathna Durga R. Manian

  DOI：10.1055/s-2005-865216

  日期：——

  An assembly of polycyclic N-heterocycles, with the ­formation of four bonds and three rings, was obtained in good yield by the sequential intramolecular 1,3-dipolar cycloaddition via the N-metallation Ag(I)-catalysed imine route and subsequent Pictet-Spengler cyclisation.

  通过 N-金属化 Ag(I)- 催化亚胺途径和随后的 Pictet-Spengler 环化，以良好的收率获得了分子内 1,3- 二极环加成的多环 N-杂环，并形成了四个键和三个环。
• Intramolecular [3⁺+2] Cycloaddition of 2-Alkenyloxy-1-naphthaldehyde Oximes
  作者：Tomio Shimizu、Yoshiyuki Hayashi、Kazuhiro Teramura

  DOI：10.1246/bcsj.58.397

  日期：1985.1

  The thermal treatment of the mixture of 2-alkenyloxy-1-naphthaldehydes and hydroxylamine hydrochloride in ethanol gave intramolecular [3++2] cycload-ducts, 1,3a,4,11c-tetrahydro-3H-naphtho[1′,2′: 5,6]pyrano[4,3-c]isoxazole hydrochlorides.

  将2-烯氧基-1-萘醛和盐酸羟胺在乙醇中的混合物进行热处理，得到分子内[3++2]环加合物，1,3a,4,11c-四氢-3H-萘并[1',2' ：5,6]吡喃并[4,3-c]异恶唑盐酸盐。
• Fulvenes acting as 4π components in an intramolecular [4+2]cycloaddition reaction: Entry into the novel 6-oxatricyclo[6.4.0.02,10]dodeca-2,11-diene ring system
  作者：M. Shanmugasundaram、R. Raghunathan

  DOI：10.1016/s0040-4039(99)00898-9

  日期：1999.6

  Intramolecular [4+2] cycloaddition of fulvenes 2a,b gives 6-oxatricyclo[6.4.0.02,10]dodeca-2,11-diene-[4,5-a]naphtho-endo 9-carboxylic acid alkyl esters 3a,b. Compounds 3a,b are the first representatives of this bridged tricyclic ring system.

  富烯2a，b的分子内[4 + 2]环加成反应得到6-氧杂三环[6.4.0.0 2,10 ] dodeca- 2,11-二烯-[4,5-a]萘内消旋9-羧酸烷基酯3a， b。化合物3a，b是该桥联的三环系统的第一个代表。
• An intramolecular Diels–Alder reaction involving fulvenes as 4π components—stereoselective synthesis of novel oxatricyclo[6.4.0.02,10] dodeca-2,11-diene ring system
  作者：S Manikandan、M Shanmugasundaram、R Raghunathan

  DOI：10.1016/s0040-4020(01)01174-7

  日期：2002.1

  Fulvenes acting as 4π components in an intramolecular [4+2] cycloaddition reaction leading to the formation of novel 6-oxatricyclo [6.4.0.02,10] dodeca-2,11-diene ring systems have been described. Importance of steric buttressing effect in promoting the reaction has been discussed.

  已经描述了在分子内[4 + 2]环加成反应中作为4π组分的ulvenes，其导致形成新的6-氧三环[6.4.0.0 2,10 ] dodeca- 2,11-二烯环系统。已经讨论了空间支撑作用在促进反应中的重要性。