3-cyclohexylidene-propionic acid ethyl ester | 18559-89-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-cyclohexylidene-propionic acid ethyl ester
• 英文别名: 3-Cyclohexyliden-propionsaeure-aethylester；cyclohexylidene-propanoic acid ethyl ester；Propanoic acid, 3-cyclohexylidene-, ethyl ester；ethyl 3-cyclohexylidenepropanoate
• CAS: 18559-89-2
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: PYGNLMKPUDZLMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  3-cyclohexylidene-propionic acid ethyl ester 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以82%的产率得到1-羟基环己烷丙酸 gamma-内酯
  参考文献：
  名称：

  Direct conversion of β,γ-unsaturated esters into lactones induced by TMS-I

  摘要：

  beta,gamma-unsaturated esters readily prepared by photodeconjugation are converted in one step into butanolides by treatment with TMS-1. the reaction has been extended to the access to alpha-alkylidene lactones.

  DOI：

  10.1016/s0040-4020(01)85681-7
• 作为产物：
  描述：

  丙烯醛缩二乙醇 在 正丁基锂 、 双氧水 、 对甲苯磺酸 作用下， 以 乙醇 、 正己烷 为溶剂， 反应 63.17h， 生成 3-cyclohexylidene-propionic acid ethyl ester
  参考文献：
  名称：

  Stereoselective Syntheses of β,γ-Unsaturated Esters and γ-Lactones:  1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene, a Protected CCH₂CO₂Et Synthon Equivalent

  摘要：

  1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene (3), prepared from N-(alpha-ethoxy-allyl)benzotriazole (1), underwent selective Horner reactions with aldehydes to give substituted dienes. Subsequent hydrolysis of these intermediates readily produced beta,gamma-unsaturated esters 2a-c in good yields. Similar reactions with ketones followed by hydrolysis of 10 produced, depending on the conditions, either the corresponding gamma,gamma-disubstituted beta,gamma-unsaturated esters 11a-d or gamma-lactones 9a-c and 13. A double lithiation process provided beta,gamma,gamma-trisubstituted beta,gamma-unsaturated esters 15, 18, and beta,gamma,gamma-trisubstituted gamma-lactone 14.

  DOI：

  10.1021/jo9701647

文献信息

• Palladium(0)-catalyzed carbonylation of allyl phosphates and allyl acetates. Selective synthesis of β,γ-unsaturated esters
  作者：Shun-Ichi Murahashi、Yasushi Imada、Yuki Taniguchi、Shin-ya Higashiura

  DOI：10.1016/s0040-4039(00)80648-6

  日期：1988.1

  Palladium catalyzed carbonylations of allyl phosphates and allyl acetates give β,γ-unsaturated esters efficiently. The latter reaction requires bromide ion as a co-catalyst.

  钯催化的烯丙基磷酸酯和乙酸烯丙酯的羰基化反应可有效地生成β，γ-不饱和酯。后一反应需要溴离子作为助催化剂。
• Facile Preparation of Functionalized 1-Substituted Cycloalkenes via an Iodine Atom Transfer Radical Addition–Elimination Process
  作者：Philippe Renaud、Daniel Meyer、Estelle Vin、Benjamin Wyler、Guillaume Lapointe

  DOI：10.1055/s-0035-1560555

  日期：——

  scalable two-step one-pot procedure for the preparation of cycloalkenes substituted with a functionalized alkyl side chain is reported. This method is based on a triethylborane-mediated iodine atom transfer radical addition (ATRA) of 1-iodoesters and related compounds to methylenecycloalkanes followed by treatment of the intermediate tertiary iodide with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to

  报道了一种有效且可扩展的两步一锅法，用于制备被官能化烷基侧链取代的环烯烃。该方法基于 1-碘酯和相关化合物与亚甲基环烷烃的三乙基硼烷介导的碘原子转移自由基加成 (ATRA)，然后用 1,8-二氮杂双环 [5.4.0] 十一碳烯处理中间体叔碘化物(DBU) 以促进选择性内源消除。
• Palladium(0)-catalyzed alkoxycarbonylation of allyl phosphates and acetates
  作者：Shunichi Murahashi、Yasushi Imada、Yuki Taniguchi、Shinya Higashiura

  DOI：10.1021/jo00058a040

  日期：1993.3

  Palladium-catalyzed alkoxycarbonylation of allyl phosphates under CO (1 atm) at 50-degrees-C proceeds highly efficiently to give the corresponding beta,gamma-unsaturated esters. The carbonylation of geranyl phosphate ((E)-11) under CO (1 atm) at 50-degrees-C gave ethyl ester of homogeranic acid ((E)-12) stereoselectively. The carbonylation takes place at the least substituted allylic positions with inversion of configuration. Typically, the methoxycarbonylation of cis-5-(methoxycarbonyl)-2-cyclohexen-1-yl phosphate (cis-16) gave trans-dimethyl 2-cyclohexene-1,5-dicarboxylate (trans-17) selectively. Alkoxycarbonylation of allyl acetates is performed for the first time in the presence of a catalytic amount of bromide ion. The reaction can be rationalized by assuming the mechanism which involves oxidative addition of palladium(0) species to allyl acetates to give pi-allylpalladium acetate, fast ligand exchange of the acetate with bromide, insertion of carbon monoxide to give acylpalladium species, and alkoxylation.
• Photochemical reactions. XIV. Additions to ethyl propiolate
  作者：G. Buechi、S. H. Feairheller

  DOI：10.1021/jo01255a027

  日期：1969.3
• 240. Fused carbon rings. Part XIII. Synthesis of derivatives of decalin containing an angular methyl group
  作者：R. P. Linstead、A. F. Millidge、A. L. Walpole

  DOI：10.1039/jr9370001140

  日期：——