乙酸环癸酯 | 7386-24-5

• 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
• 中文名称: 乙酸环癸酯
• 英文名称: acetoxycyclodecane
• 英文别名: acetic acid cyclodecyl ester；Essigsaeure-cyclodecylester；Acetoxy-cyclodecan；Cyclodecyl-acetat；Cyclodecyl acetate
• CAS: 7386-24-5
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: KNPITBTYJPSSJM-UHFFFAOYSA-N

物化性质

• LogP：
  4.356 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  乙酸环癸酯 生成 1,9-癸二烯 、 (Z)-cyclodecene 、 反式-环癸烯
  参考文献：
  名称：

  Proximity Effects. XXV. Pyrolysis of Cycloöctyl and Cyclodecyl Esters

  摘要：

  DOI：

  10.1021/ja00871a027
• 作为产物：
  描述：

  环癸酮 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 苯 为溶剂， 生成 乙酸环癸酯
  参考文献：
  名称：

  四乙酸铅与脂环族醇-I环烷醇的反应

  摘要：

  含有4至16元环的仲环烷醇已在回流的苯中用四乙酸铅处理过。已发现氧化成相应酮的难易程度遵循脂环化合物涉及sp 3 → sp 2的反应的反应顺序。环碳杂化的变化，以及导致环打开的β片段的数量与与碳环相关的总应变相符。分子内醚形成的产率似乎取决于过渡态的环大小和构象因素。它从环己醇增加到环辛醇，对于环十二烷醇急剧下降，在环十六烷醇中达到最大值。在环癸醇的情况下获得的主要醚是反式-1，2-环氧环癸烷。

  DOI：

  10.1016/s0040-4020(01)88403-9

文献信息

• Zur Kenntnis des Kohlenstoffringes. 49. Mitteilung. Vielgliedrige Cyclanole und Cyclanol-acetate
  作者：Margrit Kobelt、P. Barman、V. Prelog、L. Ruzicka

  DOI：10.1002/hlca.19490320136

  日期：1949.2.1

  Die ringhomologen Cyclanole mit 8–20 Ringgliedern, von welchen diejenigen mit einem 10-, 11-, 12-, 16-, 18-, 19- und 20-gliedrigen Ring bisher nicht beschrieben worden waren, wurden durch katalytische Hydrierung der entsprechenden Cyclanone mit Raney-Nickel in alkoholischer Lösung hergestellt.

  致死性致癌物Cyclanole mit 8-20 Ringgliedern，welchen diejenigen mit einem 10-，11-，12-，16-，18-，19-和20-glidrigen Raney -Nickel在AlkoholischerLösunghergestellt中。
• Conformational Study of Cyclodecane and Substituted Cyclodecanes by Dynamic NMR Spectroscopy and Computational Methods
  作者：Diwakar M. Pawar、Sumona V. Smith、Hugh L. Mark、Rhonda M. Odom、Eric A. Noe

  DOI：10.1021/ja973116c

  日期：1998.10.1

  Low-temperature C-13 NMR spectra of cyclodecane (1) showed the presence of a minor conformation, assigned to the twist-boat-chair-chair (TBCC), in addition to the expected boat-chair-boat (BCB). If only the TBCC and BCB conformations were assumed to be appreciably populated, then a free-energy difference between the two conformations of 0.73 +/- 0.3 kcal/mol could be obtained from the five area measurements over a temperature range of -148.6 to -131.0 degrees C, with populations of 5.2 and 94.8% for the TBCC and BCB conformations at -146.1 degrees C. However, an alternative description of the conformations of 1 was suggested by the ab initio calculations, which predicted that the twist-boat-chair (TBC) and TBCC conformations have comparable free energies and populations. Equal amounts of TBCC and TBC would give populations of 5.2, 5.2, and 89.6% and relative free energies of 0.72, 0.72, and 0.00 kcal/mol for the TBCC, TBC, and BCB conformations at -146.1 degrees C, based on the experimental areas at this temperature. The experimental spectra could neither confirm nor disprove the presence of the TBC. Saunders' calculations of the strain energies of 1 using Allinger's MM3 program were reproduced to obtain a complete set of these parameters and drawings of the conformations, and free energies and populations were obtained at +25 and -171.1 degrees C. Free energies were also calculated at the HF/6-31G* and HF/6-311G* levels, and chemical shifts were obtained for three conformations at the HF/6-311G* level by the GIAO method. Chlorocyclodecane (2) was shown by C-13 and H-1 NMR spectroscopy to have three conformations at -165.5 degrees C. To aid in conformational assignments, the C-13 chemical shifts were calculated for all of the BCB and TBCC conformations of 2 using the GIAO method at the HF/6-311G* level. The free energies for each of the possible BCB, TBCC, and TBC conformations were also calculated using Allinger's MM3 program. From the line shape changes in the experimental C-13 NMR spectra, the free-energy barriers, a consideration of the X-ray structures of substituted cyclodecanes, and these calculated chemical shifts and free energies, the three conformations of 2 at -165.5 degrees C were suggested to be 2e BCB (31.2%), 2a BCB (14.9%), and a TBCC conformation (53.9%) (numbering as in Figure 1); the 2e and 2a BCB assignments could be reversed. Free-energy barriers for interconversion of BCB conformations of 2 at -159.8 degrees C were 5.4 +/- 0.2 and 5.5 +/- 0.2 kcal/mol, and the free-energy barriers at -120.9 degrees C for equilibration of the TBCC conformation with the rapidly interconverting BCB conformations were 7.07 +/- 0.2 and 7.08 +/- 0.2 kcal/mol. The C-13 NMR spectrum of cyclodecyl acetate (3) at -160.0 degrees C showed a similar pattern of chemical shifts and intensities for the substituted ring carbon.
• CEKOVIC, Z.;MUSICKI, B.;BOSNJAK, J.;MIHAILOVIC, M. LJ., GLASN. XEM. DRUSH. BEOGRAD, 1983, 48, NO 10, 681-690
  作者：CEKOVIC, Z.、MUSICKI, B.、BOSNJAK, J.、MIHAILOVIC, M. LJ.

  DOI：——

  日期：——
• <b>Proximity Effects. XXV. Pyrolysis of Cycloöctyl and Cyclodecyl Esters</b>
  作者：Arthur C. Cope、Mary J. Youngquist

  DOI：10.1021/ja00871a027

  日期：1962.6
• The reaction of lead tetraacetate with alicyclic alcohols—I cycloalkanols
  作者：M.Lj. Mihailovič、Ž. Čeković、V. Andrejević、R. Matić、D. Jeremić

  DOI：10.1016/s0040-4020(01)88403-9

  日期：1968.1

  Secondary cycloalkanols, containing 4- to 16-membered rings, have been treated with lead tetraacetate in refluxing benzene. It was found that the ease of oxidation to the corresponding ketones follows the reactivity order of reactions of alicyclic compounds involving an sp3 → sp2 ring carbon hybridization change, and that the amount of β-fragmentation resulting in opening of the ring is in accord with

  含有4至16元环的仲环烷醇已在回流的苯中用四乙酸铅处理过。已发现氧化成相应酮的难易程度遵循脂环化合物涉及sp 3 → sp 2的反应的反应顺序。环碳杂化的变化，以及导致环打开的β片段的数量与与碳环相关的总应变相符。分子内醚形成的产率似乎取决于过渡态的环大小和构象因素。它从环己醇增加到环辛醇，对于环十二烷醇急剧下降，在环十六烷醇中达到最大值。在环癸醇的情况下获得的主要醚是反式-1，2-环氧环癸烷。