(E)-3-戊烯酸乙酯 | 3724-66-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (E)-3-戊烯酸乙酯
• 英文名称: ethyl (E)-3-pentenoate
• 英文别名: ethyl 3-pentenoate；ethyl (E)-pent-3-enoate；ethyl pent-3-enoate；pent-3t-enoic acid ethyl ester；Pent-3t-ensaeure-aethylester；trans-Pent-3-ensaeure-aethylester；ethyl 3-trans-pentenoate；(E)-3-Pentenoic acid ethyl ester
• CAS: 3724-66-1
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: UMLQAWUDAFCGGS-HWKANZROSA-N

物化性质

• 沸点：
  145-150 °C
• 密度：
  0.907±0.06 g/cm3(Predicted)
• LogP：
  2.059 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  (E)-3-戊烯酸乙酯 在 Rh on carbon 吡啶 、 六甲基磷酰三胺 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 苄基三乙基氯化铵 、 氢气 、 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 异丙醇 为溶剂， 反应 25.5h， 生成 (23S,24R,25R)-24,25-(dichloromethylene)-23-ethyl-6β-methoxy-3α,5-cyclocholestane
  参考文献：
  名称：

  Biosynthetic studies of marine lipids. 37. Enzymatic desaturation of 24(S)-methylcholesterol to 23,24-methylenecholesterol, norficisterol, and norhebesterol. Further evidence for a unified biosynthesis of marine sterols with unique side chains

  摘要：

  The enzymatic desaturation of 24(S)-methylcholesterol to 23,24-methylenecholesterol, 29-norhebesterol, and norficisterol was demonstrated in the sponge, Petrosia ficiformis, by feeding the [3-H-3]-labeled analogue. [3-H-3]-24(R)-Methylcholesterol and [3-H-3]-24(R)-ethylcholesterol were not metabolized, though comparable amounts of each of the three precursors were isolated from the sponge. [3-H-3]Cholesterol was converted to 24-methylenecholesterol and clionasterol, presumably by its desaturation to desmosterol and subsequent biomethylation. The structure and stereochemistry of 29-norhebesterol was proven by partial synthesis. The possible role of a similar enzymatic process in the biosynthesis of cyclopropene-containing sterols is also considered.

  DOI：

  10.1021/ja00027a037
• 作为产物：
  描述：

  3-戊烯酸 生成 (E)-3-戊烯酸乙酯
  参考文献：
  名称：

  Prochazka,M.; Palecek,M., Collection of Czechoslovak Chemical Communications, 1970, vol. 35, p. 1399 - 1405

  摘要：

  DOI：

文献信息

• Dalton communications. Carbonylation of organic halides catalysed by rhodium triethylphosphine complexes
  作者：Michael C. Simpson、Marc J. Payne、David J . Cole-Hamilton

  DOI：10.1039/dt9940002899

  日期：——

  Allyl and benzyl halides but not phenyl or propyl halides have been carbonylated in ethanol in the presence of rhodium triethylphosphine complexes to their respective butenoic or benzylic esters; no added base was required.

  在三乙基膦铑络合物的存在下，乙醇中将烯丙基卤和苄基卤化物而不是苯基或丙基卤化物羰基化为它们各自的丁烯酸酯或苄基酯；无需添加基础。
• Studies in decarboxylation. Part 13. The incursion of a stepwise mechanism in the gas-phase decarboxylation of cyclopropylacetic acids
  作者：David B. Bigley、Clive L. Fetter、Michael J. Clarke

  DOI：10.1039/p29800000553

  日期：——

  cyclopropylacetic acids (I)–(IV) have been decarboxylated in the temperature range 720–820 K. It is demonstrated that at 725 K, 2′,2′-dimethylcyclopropylacetic acid is decarboxylated by both concerted and stepwise mechanisms. The latter is favoured by higher temperature. Cyclopropylacetic acid is decarboxylated by the concerted mechanism at 725 K, but also exhibits the stepwise mechanism at higher temperature

  环丙基乙酸（I）-（IV）已在720-820 K的温度范围内脱羧。事实证明，在725 K下，2'，2'-二甲基环丙基乙酸通过协同作用和逐步作用机理均被脱羧。较高的温度有利于后者。环丙基乙酸通过协同机理在725 K下脱羧，但在较高温度下也表现出逐步机理。
• Divergent Reactivity of α,α-Disubstituted Alkenyl Hydrazones: Bench Stable Cyclopropylcarbinyl Equivalents
  作者：Nina F. C. Ritchie、Adam J. Zahara、Sidney M. Wilkerson-Hill

  DOI：10.1021/jacs.1c12881

  日期：2022.2.9

  N-tosylhydrazones using Pd-catalyzed cross-coupling conditions, which enable the Z-selective synthesis of 3-aryl-1,4-dienes and gem-dialkyl vinylcyclopropanes. We found that the dialkylbiaryl phosphine ligand SPhos was the optimal ligand for this transformation producing skipped dienes in up to 83% isolated yield. The ratio of skipped diene to vinylcyclopropane is dependent on both the structure of the α,α-disubstituted

  在这里，我们报告了使用 Pd 催化的交叉偶联条件的 2,2-二烷基-3-( E )-烯基N-甲苯磺酰腙的不同反应性，这使得Z选择性合成 3-aryl-1,4-二烯和偕二烷基乙烯基环丙烷。我们发现二烷基联芳基膦配体 SPhos 是这种转化产生跳跃二烯的最佳配体，分离产率高达 83%。跳过的二烯与乙烯基环丙烷的比例取决于 α,α-二取代腙和芳基卤化物配对物的结构。使用空间位阻芳基溴提供反式-环丙烷产品选择性地高达 69% 的产率。该反应具有立体特异性和立体选择性，并与竞争的 1,2-烯基迁移途径一起发生。
• Stereochemical consequences in the deprotonation of enoates
  作者：Paul Galatsis、Jeffrey J. Manwell、Scott D. Millan

  DOI：10.1016/0040-4039(96)01144-6

  日期：1996.7

  A cyclic transition structure for the deprotonation of enoates was proposed to rationalize the geometry of the deconjugated olefin and the substrate reactivity patterns.

  提出了一种用于烯键的去质子化的环状过渡结构，以合理化去共轭烯烃的几何形状和底物的反应模式。
• Organic syntheses by means of noble metal compounds—XL
  作者：S. Imamura、J. Tsuji

  DOI：10.1016/s0040-4020(01)82955-0

  日期：1969.1

  Palladium catalysed carbonylation of allylic ethers, especially 1,4-diethoxy-2-butene has been carried out. Hexenedioate, 5-ethoxy-3-pentenoate, 2-ethoxymethyl-3-butenoate, 3-pentenoate, pentadienoate were obtained and the mechanism of the allylic carbonylation and competing reactions are discussed.

  已经进行了钯催化的烯丙基醚，特别是1，4-二乙氧基-2-丁烯的羰基化。获得了己烯二酸酯，5-乙氧基-3-戊烯酸酯，2-乙氧基甲基-3-丁烯酸酯，3-戊烯酸酯，戊二烯酸酯，并讨论了烯丙基羰基化和竞争反应的机理。