Ethyl 2-ethoxy-4-phenyl-1,3-cyclopentadiene-1-carboxylate | 136848-45-8

• 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: Ethyl 2-ethoxy-4-phenyl-1,3-cyclopentadiene-1-carboxylate
• 英文别名: ethyl 2-ethoxy-4-phenylcyclopenta-1,3-diene-1-carboxylate
• CAS: 136848-45-8
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: CHJMTOVYROFIEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 2-ethoxy-4-phenyl-1,3-cyclopentadiene-1-carboxylate 在 盐酸 作用下， 以 氯仿 为溶剂， 以99%的产率得到Ethyl 2-oxo-4-phenyl-3-cyclopentene-1-carboxylate
  参考文献：
  名称：

  亚丙基三苯基膦和α-卤代羰基化合物的环戊烯酮

  摘要：

  亚烷基三苯基磷烷3与α-卤代酮和α-卤代硫代酯反应，在碱的存在下，通过[3 + 2]环化过程得到2-乙氧基环戊二烯。2-乙氧基环戊二烯的弱酸处理为环戊烯酮提供了一条新途径。

  DOI：

  10.1016/0040-4039(91)80029-6
• 作为产物：
  描述：

  ethyl (Z)-4-[bromo(triphenyl)-λ5-phosphanyl]-3-ethoxy-2-phenacylbut-3-enoate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 Ethyl 2-ethoxy-4-phenyl-1,3-cyclopentadiene-1-carboxylate
  参考文献：
  名称：

  亚丙基三苯基膦和α-卤代羰基化合物的环戊烯酮

  摘要：

  亚烷基三苯基磷烷3与α-卤代酮和α-卤代硫代酯反应，在碱的存在下，通过[3 + 2]环化过程得到2-乙氧基环戊二烯。2-乙氧基环戊二烯的弱酸处理为环戊烯酮提供了一条新途径。

  DOI：

  10.1016/0040-4039(91)80029-6

文献信息

• Reaction of trisubstituted alkenes with iron porphyrin carbenes: facile synthesis of tetrasubstituted dienes and cyclopentadienes
  作者：Peng Wang、Saihu Liao、Sunewang R. Wang、Run-Duo Gao、Yong Tang

  DOI：10.1039/c3cc44092c

  日期：——

  The unprecedented reaction of trisubstituted alkenes with iron porphyrin carbenes has been successfully developed. Both multiply substituted 1,3-butadiene and cyclopentadiene products are readily accessible with high efficiency and selectivity in good yields.

  已经成功开发了三取代烯烃与卟啉铁甲酸酯的空前反应。多取代的1，3-丁二烯和环戊二烯产物都容易以高产率和高效率和选择性地获得。
• An Anion Receptor Based on Poly-Substituted Cobalticinium Complexes
  作者：Nobuko Komatsuzaki、Mitsunari Uno、Kazuhiko Shirai、Yoshio Takai、Takanori Tanaka、Masami Sawada、Shigetoshi Takahashi

  DOI：10.1246/bcsj.69.17

  日期：1996.1

  Various derivatives of poly-substituted cobalticinium complexes have been synthesized by using substituted cyclopentadienes with a convertible carboxylic group. By 1H NMR titration experiments, these complexes were shown to behave as a receptor for anions such as Cl−, Br−, AcO−, and p-TsO−. Planar-chiral anilide derivative 3a showed chiral recognition toward camphor-10-sulfonate though the difference of the association constants was 10%. The molecular structure including the absolute configuration of 3a have been established by an X-ray crystallographic analysis. The results suggest the hydrophobic cavity constructed by the substituents on the cyclopentadienyl ligands may be an important component for the successful anion complexation.

  通过使用带有可转换羧基的取代环戊二烯，合成了多种多取代钴钿络合物衍生物。通过 1H NMR 滴定实验，这些配合物被证明可作为 Cl-、Br-、AcO- 和 p-TsO- 等阴离子的受体。平面手性苯胺衍生物 3a 显示出对樟脑-10-磺酸盐的手性识别能力，尽管两者的结合常数相差 10%。通过 X 射线晶体学分析，确定了 3a 的分子结构和绝对构型。结果表明，环戊二烯配体上的取代基所构建的疏水空腔可能是阴离子成功络合的重要组成部分。
• Allylidenetriphenylphosphorane as a bifunctional reagent: synthesis of cyclopentenones and .alpha.,.beta.-unsaturated ketones with [3-(alkoxycarbonyl)-2-ethoxy-2-propenylidene]triphenylphosphorane
  作者：Minoru Hatanaka、Yuichiro Himeda、Ritsuo Imashiro、Yasuhiro Tanaka、Ikuo Ueda

  DOI：10.1021/jo00080a019

  日期：1994.1

  When (3-(ethoxycarbonyl)-2-ethoxy-2-propenylidene) triphenylphosphorane (6) was allowed to react with cu-bromo ketones 8a-d in dichloromethane in the presence of Cs2CO3 at room temperature, a [3 + 2] annulation occurred and led to the formation of the corresponding 2-ethoxycyclopentadienes 9a-d in excellent yields. Similarly, bromo thioester 8g underwent the annulation to give 4-(ethylthio)-cyclopentadiene 9g. Secondary bromides 2-bromo-3-pentanone and 2-bromocyclohexanone also afforded tetrasubstituted cyclopentadienes 9e and 9f in moderate yields when 2 equiv of 6 was used. The annulation is believed to proceed through a sequence involving a stepwise alkylation at the gamma position of 6 and an intramolecular Wittig reaction because of the fact that intermediate 11 was isolated. The resulting 2-ethoxycyclopentadienes 9a-g were converted quantitatively into the corresponding cyclopentenones 10a-g upon mild acid treatment. Furthermore, allylidenetriphenylphosphorane underwent a carbon elongation at both ends of the three-carbon unit via an alkylation-Wittig reaction sequence. (3-(tert-Butoxycarbonyl)-2-ethoxy-2-propenylidene)triphenylphosphorane (7) reacted first with alkyl halides and then with aldehydes in the presence of Cs2CO3 to give enol ethers 23a-f, which were converted into alpha,beta-unsaturated ketones 20, 21, and 25c-f by hydrolysis of the enol ether and then decarboxylation. In this way, shogaol (29), the pungent principle component of ginger, was conveniently synthesized starting from 2-methoxy-4-methylphenol.