(E)-5-<2-(2-Naphthalenyloxy)-3-oxo-1-cyclohexen-1-yl>-2-pentenoic Acid Ethyl Ester | 135525-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-5-<2-(2-Naphthalenyloxy)-3-oxo-1-cyclohexen-1-yl>-2-pentenoic Acid Ethyl Ester
• 英文别名: ethyl (E)-5-(2-naphthalen-2-yloxy-3-oxocyclohexen-1-yl)pent-2-enoate
• CAS: 135525-35-8
• 化学式: C₂₃H₂₄O₄
• 分子量: 364.441
• InChiKey: RJKGEDPCZFWCSL-AWNIVKPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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)-5-<2-(2-Naphthalenyloxy)-3-oxo-1-cyclohexen-1-yl>-2-pentenoic Acid Ethyl Ester 以 甲苯 为溶剂， 反应 0.58h， 以85%的产率得到1,2,3,4,5,6-Hexahydro-4-oxo-(4aα,5β,6α,6aα,12cβ)-12bH-4a,6a-epoxy-5,12c-ethano-benzophenanthrene-6-carboxylic Acid Ethyl Ester
  参考文献：
  名称：

  Intramolecular addition reactions of carbonyl ylides formed during photocyclization of aryl vinyl ethers

  摘要：

  Photocyclization of aryl vinyl ethers reportedly proceeds via carbonyl ylide intermediates. The photochemical behavior of several aryl vinyl ethers, which incorporate a pendant alkene side chain, was explored. Naphthyl vinyl ethers 1c and 1d provided products that are consistent with photocyclization and subsequent intramolecular ylide-alkene addition. Product distribution is influenced by solvent and temperature effects. Thus, irradiation of 1c in toluene provides 9a in 87% yield. However, irradiation of 1c in methanol/toluene (1:1) provides 3c (45%), 11 (24%), and 12 (23%). Product 12 results from photoinitiated intramolecular [2 + 2] cycloaddition of the butenoate ester side chain to the naphthalene system.

  DOI：

  10.1021/jo00019a020
• 作为产物：
  描述：

  3-乙氧基-2-环己烯-1-酮 在 N,N-二甲基丙烯基脲 、 sodium hydroxide 、 水 、 双氧水 、 草酸 、 potassium hydride 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 91.5h， 生成 (E)-5-<2-(2-Naphthalenyloxy)-3-oxo-1-cyclohexen-1-yl>-2-pentenoic Acid Ethyl Ester
  参考文献：
  名称：

  Intramolecular addition reactions of carbonyl ylides formed during photocyclization of aryl vinyl ethers

  摘要：

  Photocyclization of aryl vinyl ethers reportedly proceeds via carbonyl ylide intermediates. The photochemical behavior of several aryl vinyl ethers, which incorporate a pendant alkene side chain, was explored. Naphthyl vinyl ethers 1c and 1d provided products that are consistent with photocyclization and subsequent intramolecular ylide-alkene addition. Product distribution is influenced by solvent and temperature effects. Thus, irradiation of 1c in toluene provides 9a in 87% yield. However, irradiation of 1c in methanol/toluene (1:1) provides 3c (45%), 11 (24%), and 12 (23%). Product 12 results from photoinitiated intramolecular [2 + 2] cycloaddition of the butenoate ester side chain to the naphthalene system.

  DOI：

  10.1021/jo00019a020

文献信息

• Photochemistry of Aryl Vinyl Sulfides and Aryl Vinyl Ethers:  Evidence for the Formation of Thiocarbonyl and Carbonyl Ylides
  作者：James P. Dittami、Yalin Luo、David Moss、W. Grant McGimpsey

  DOI：10.1021/jo9604649

  日期：1996.1.1

  Aryl vinyl thioethers 5a and 9a and aryl vinyl ethers 5b and 9b form ylide intermediates following laser irradiation at 308 nm. In benzene, the ylides possess long-lived absorption bands in the 600-800 nm region with a second weaker band at approximately 460 nm. In methanol, a known quencher of zwitterionic species, the lifetimes are reduced significantly. The decay kinetics measured within the long

  芳基乙烯基硫醚5a和9a以及芳基乙烯基醚5b和9b在308nm激光照射后形成ylide中间体。在苯中，乙炔化物在600-800 nm区域具有长寿命的吸收带，在约460 nm处具有第二弱的吸收带。在已知的两性离子物质淬灭剂甲醇中，寿命会大大缩短。在长波吸收包络线内测得的衰减动力学随波长变化，表明存在一种以上的叶立德物质。在芳基乙烯基醚的情况下，经由类似萘的三重态发生酰基化物的形成，而对于硫醚，则该前驱体的多样性可以是单重态或三重态。苯中5a和5b的产物形成涉及叶立德的闭环反应，生成二氢噻吩和二氢呋喃产物，分别。对于短时间的照射（无论是灯还是激光），观察到顺式和反式融合产物的混合物，而对于长时间的照射，仅检测到了顺式融合的化合物，这表明了将反式转化为顺式的光烯化机理。除了衍生自闭环的产物外，9a还提供分子内加成产物12。相反，衍生自9b的叶立德产生[3 + 2]环加成产物13。
• Intramolecular addition reactions of carbonyl ylides formed during photocyclization of aryl vinyl ethers
  作者：James P. Dittami、Xiao Yi Nie、Hong Nie、H. Ramanathan、Scott Breining、Jon Bordner、Debra L. Decosta、Jeffrey Kiplinger、Philip Reiche、Richard Ware

  DOI：10.1021/jo00019a020

  日期：1991.9

  Photocyclization of aryl vinyl ethers reportedly proceeds via carbonyl ylide intermediates. The photochemical behavior of several aryl vinyl ethers, which incorporate a pendant alkene side chain, was explored. Naphthyl vinyl ethers 1c and 1d provided products that are consistent with photocyclization and subsequent intramolecular ylide-alkene addition. Product distribution is influenced by solvent and temperature effects. Thus, irradiation of 1c in toluene provides 9a in 87% yield. However, irradiation of 1c in methanol/toluene (1:1) provides 3c (45%), 11 (24%), and 12 (23%). Product 12 results from photoinitiated intramolecular [2 + 2] cycloaddition of the butenoate ester side chain to the naphthalene system.