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：——