ethyl 2,5-cycloheptadienecarboxylate | 72184-78-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2,5-cycloheptadienecarboxylate
• 英文别名: Ethyl cyclohepta-2,5-diene-1-carboxylate
• CAS: 72184-78-2
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: PTSLEZWYLKCORO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 2,5-cycloheptadienecarboxylate 在 氢氧化钾 作用下， 生成 2,5-Cycloheptadienecarboxylic acid
  参考文献：
  名称：

  Kajiwara, Tadahiko; Sasaki, Yasuhi; Kimura, Fumiko, Agricultural and Biological Chemistry, 1981, vol. 45, # 6, p. 1461 - 1466

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-3-((1S,2S)-2-Vinyl-cyclopropyl)-acrylic acid ethyl ester 生成 ethyl 2,5-cycloheptadienecarboxylate
  参考文献：
  名称：

  Akintobi,T. et al., Liebigs Annalen der Chemie, 1979, p. 986 - 996

  摘要：

  DOI：

文献信息

• Synthesis of (±)-Desmarestene and (±)-Viridiene, the Two Sperm Releasing and Attracting Pheromones from the Brown Algae<i>Desmarestia aculeata</i>and<i>Desmarestia viridis</i>
  作者：Wilhelm Boland、Karin Jakoby、Lothar Jaenicke

  DOI：10.1002/hlca.19820650742

  日期：1982.11.3

  Desmarestene 1 6-(1Z,3-butadienyl)-1,4-cycloheptadiene and viridiene 3cis-3-(1Z, 3-butadienyl)-4-vinylcyclopentene are chemical messengers for male gametes of the brown algae Desmarestia aculeate and Desmarestia viridis. Total syntheses of 1, 3 and their stereoisomers 1a, 3a-c are reported. Gas-chromatographic comparison of synthetic 1 and 3 with the corresponding natural products has established their

  Desmarestene 1 6-（1 Z，3-丁二烯基）-1,4-环庚二烯和viridiene 3顺-3-（1 Z，3-丁二烯基）-4-乙烯基环戊烯是褐藻雄配子的化学信使Desmarestia aculeate和Desmarestia贻贝。的全合成1，3和其立体异构体1a中，图3a - Ç报告。合成1和3与相应的天然产物的气相色谱比较确定了它们的结构特征。
• Tandem Reduction−Chloroallylboration of Esters:  Asymmetric Synthesis of Lamoxirene, the Spermatozoid Releasing and Attracting Pheromone of the Laminariales (Phaeophyceae)
  作者：Christian Hertweck、Wilhelm Boland

  DOI：10.1021/jo991629r

  日期：2000.4.1

  The asymmetric synthesis of all four stereoisomers of lamoxirene (cis-2-cyclohepta-2,5-dienyl-3-vinyloxirane), the spermatozoid-releasing and -attracting pheromone of the Laminariales (Phaeophyceae), is reported. Chiral ethyl cyclohepta-2,5-diene carboxylates, prepared by a divinylcyclopropane Cope rearrangement, were effectively alkylated by means of a novel tandem DIBAL-H reduction/asymmetric al

  据报道，拉莫西林的全部四个立体异构体（顺式-2-环庚基-2,5-二烯基-3-乙烯基环氧乙烷），海带（精科）的精子释放和吸引信息素的不对称合成。通过二乙烯基环丙烷Cope重排制备的手性乙基环庚-2,5-二烯羧酸酯通过新颖的串联DIBAL-H还原/不对称α-氯烯丙基化反应使用（Z）-γ-氯代烯丙基op基樟脑基硼烷有效地烷基化。随后的顺-α-氯醇用DBU转化为相应的乙烯基环氧乙烷，从而以良好的化学性质和优异的光学收率（90-97％ee）提供了信息素的所有四个异构体。精子释放试验使用的是同生生长的物种指状芽孢杆菌，hyperborea和L. saccharina，并建立了（1'S，2R，
• Highly efficient synthesis of (±)-lamoxirene, the gamete-releasing and gamete-attracting pheromone of the Laminariales (Phaeophyta)
  作者：Christian Hertweck、Wilhelm Boland

  DOI：10.1016/s0040-4020(97)01008-9

  日期：1997.10

  An efficient and highly diastereoselective synthesis of lamoxirene (cis-2-cyclohepta-2,5-dienyl-3-vinyloxirane, 4), the gamete releasing and -attracting pheromone of the Laminariales (Phaeophyceae), is reported. Ethyl cyclohepta-2,5-diene carboxylate (7) is effectively alkylated to provide the syn-alpha-chlorohydrin 8 via reductive chloroallylboration with DIBAL-H and (Z)-gamma-chloroallyl-BBN. Cyclisation of the chlorohydrin 8 is readily achieved with DBU yielding the pheromone in 25% overall yield from the cyclopropyl ester 5. (C) 1997 Elsevier Science Ltd.
• Kajiwara, Tadahiko; Sasaki, Yasuhi; Kimura, Fumiko, Agricultural and Biological Chemistry, 1981, vol. 45, # 6, p. 1461 - 1466
  作者：Kajiwara, Tadahiko、Sasaki, Yasuhi、Kimura, Fumiko、Hatanaka, Akikazu

  DOI：——

  日期：——
• Akintobi,T. et al., Liebigs Annalen der Chemie, 1979, p. 986 - 996
  作者：Akintobi,T. et al.

  DOI：——

  日期：——