(E)-tetradec-8-en-7-ol | 134361-89-0

• 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: (E)-tetradec-8-en-7-ol
• 英文别名: 8-Tetradecen-7-ol
• CAS: 134361-89-0
• 化学式: C₁₄H₂₈O
• 分子量: 212.376
• InChiKey: DBPMPGDITUYMJH-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-tetradec-8-en-7-ol 在 manganese(IV) oxide 作用下， 以 正己烷 为溶剂， 反应 1.0h， 以97%的产率得到8-Tetradecen-7-one
  参考文献：
  名称：

  Theoretical and Experimental Studies of Regioselectivity in Selenoxide Elimination

  摘要：

  In order to gain insight into the mechanism of selenoxide elimination, the transition state structures have been determined by applying the ab initio MO method to the elimination for systems having a simplified skeleton, CH2(Y)CH(Se(O)CH3)CH3 (Y OCH3, OH, CN and Cl). The calculations show that an allylic alkyl ether and an allylic alcohol should be produced preferentially in the case of Y = OCH3 and OH, respectively, whereas a vinylic cyanide should be the major product in the case of Y = CN. The chloro-substituted model has given a result most consistent with the methoxy-substituted model. The elimination occurs via a transition state with a five-membered ring structure, and the breaking of the C-beta-H bond takes place earlier than that of the Se-C-alpha bond, in the favorable path. The asynchronous nature of bond breaking is quite conspicuous in the cyano-substituted model, relative to the other systems. For comparison with the theoretical results, beta-methoxy-, beta-hydroxy-, beta-cyano-, and beta-chloro-substituted selenides were newly synthesized from trans-7-tetradecene, respectively, and were oxidized by H2O2 in tetrahydrofuran or in carbon tetrachloride. The regioselectivity observed for the elimination, i.e., the formation of a vinylic compound from the beta-cyano selenide and a mixture of allylic and vinylic products from the beta-chloro selenide, agrees well with the theoretical calculations. The difference in the activation energies of the two paths calculated for the model species is not large enough in the mthoxy- and hydroxy-substituted selenides to explain the almost; complete formation of an allylic compound in the physical experiments.

  DOI：

  10.1021/jo00097a029
• 作为产物：
  描述：

  (己基磺酰基)苯 在 正丁基锂 、 对甲苯磺酸 作用下， 以 水 、 丙酮 为溶剂， 反应 24.5h， 生成 (E)-tetradec-8-en-7-ol
  参考文献：
  名称：

  Masnyk, Marek; Wicha, Jerzy, Chemische Berichte, 1994, vol. 127, # 4, p. 677 - 684

  摘要：

  DOI：

文献信息

• SASAKI, KAZUAKI;MORI, TOSHIHARU;DOI, YOSHITAKA;KAWACHI, AKINORI;ASO, YOSH+, CHEM. LETT.,(1991) N, C. 415-418
  作者：SASAKI, KAZUAKI、MORI, TOSHIHARU、DOI, YOSHITAKA、KAWACHI, AKINORI、ASO, YOSH+

  DOI：——

  日期：——
• LABAR D.; DUMONT W.; HEVESI L.; KRIEF A., TETRAHEDRON LETT., 1978, NO 13, 1145-1148
  作者：LABAR D.、 DUMONT W.、 HEVESI L.、 KRIEF A.

  DOI：——

  日期：——
• LABAR D.; HEVESI L.; DUMONT W.; KRIEF A., TETRAHEDRON LETT., 1978, NO 13, 1141-1144
  作者：LABAR D.、 HEVESI L.、 DUMONT W.、 KRIEF A.

  DOI：——

  日期：——
• Theoretical and Experimental Studies of Regioselectivity in Selenoxide Elimination
  作者：Noboru Kondo、Hiroyuki Fueno、Hiroshi Fujimoto、Mineyuki Makino、Hiroaki Nakaoka、Ikuo Aoki、Sakae Uemura

  DOI：10.1021/jo00097a029

  日期：1994.9

  In order to gain insight into the mechanism of selenoxide elimination, the transition state structures have been determined by applying the ab initio MO method to the elimination for systems having a simplified skeleton, CH2(Y)CH(Se(O)CH3)CH3 (Y OCH3, OH, CN and Cl). The calculations show that an allylic alkyl ether and an allylic alcohol should be produced preferentially in the case of Y = OCH3 and OH, respectively, whereas a vinylic cyanide should be the major product in the case of Y = CN. The chloro-substituted model has given a result most consistent with the methoxy-substituted model. The elimination occurs via a transition state with a five-membered ring structure, and the breaking of the C-beta-H bond takes place earlier than that of the Se-C-alpha bond, in the favorable path. The asynchronous nature of bond breaking is quite conspicuous in the cyano-substituted model, relative to the other systems. For comparison with the theoretical results, beta-methoxy-, beta-hydroxy-, beta-cyano-, and beta-chloro-substituted selenides were newly synthesized from trans-7-tetradecene, respectively, and were oxidized by H2O2 in tetrahydrofuran or in carbon tetrachloride. The regioselectivity observed for the elimination, i.e., the formation of a vinylic compound from the beta-cyano selenide and a mixture of allylic and vinylic products from the beta-chloro selenide, agrees well with the theoretical calculations. The difference in the activation energies of the two paths calculated for the model species is not large enough in the mthoxy- and hydroxy-substituted selenides to explain the almost; complete formation of an allylic compound in the physical experiments.
• Masnyk, Marek; Wicha, Jerzy, Chemische Berichte, 1994, vol. 127, # 4, p. 677 - 684
  作者：Masnyk, Marek、Wicha, Jerzy

  DOI：——

  日期：——