(Z)-Dec-5-en-3-ol | 145104-09-2

• 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: (Z)-Dec-5-en-3-ol
• 英文别名: (Z)-dec-5-en-3-ol
• CAS: 145104-09-2
• 化学式: C₁₀H₂₀O
• 分子量: 156.268
• InChiKey: MXQZMRCGLIWKRV-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (Z)-Dec-5-en-3-ol 在 碘 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 以60%的产率得到(2SR,3SR,5RS)-2-Butyl-5-ethyl-3-iodotetrahydrofuran
  参考文献：
  名称：

  Iodoetherification of homoallylic alcohols : A stereoselective approach to tetrahydrofurans

  摘要：

  Iodoetherification of homoallylic alcohols proceeds efficiently and with high levels of stereoselection by a 5-endo-trig process when anhydrous acetonitrile is used as the solvent.

  DOI：

  10.1016/s0040-4039(00)79029-0
• 作为产物：
  描述：

  1-hexynyllithium 在 Pd-BaSO₄ 喹啉 、 三氟化硼乙醚 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 (Z)-Dec-5-en-3-ol
  参考文献：
  名称：

  A new, highly stereoselective approach to pyrrolidines via overall 5-endo-trig cyclisations of homoallylic tosylamides

  摘要：

  E-高烯丙基对甲苯磺酰胺 7 的碘环化反应，根据反应条件的不同，分别以优异的产率生成 2,5-反式或 2,5-顺式-3-碘吡咯烷（10 或 11）。

  DOI：

  10.1039/cc9960000915

文献信息

• A stereochemically flexible approach to pyrrolidines based on 5-endo-trig iodocyclisations of homoallylic sulfonamides
  作者：Andrew D. Jones、David W. Knight、David E. Hibbs

  DOI：10.1039/b008537p

  日期：——

  5-endo-trig Iodocyclisations of the (E)-homoallylic sulfonamides 24 in the presence of potassium carbonate give excellent yields of trans-2,5-disubstituted-3-iodopyrrolidines 36. In the absence of base, these initial kinetic products undergo rapid isomerization to the corresponding cis-2,5-disubstituted pyrrolidines 37 by a ring opening–reclosure mechanism to these thermodynamic isomers. Octahydroindole derivatives 40 and 41 can be similarly obtained from the alk-2-enylcyclohexylsulfonamides 31 and 32. Attempted 5-endo-trig cyclisations of homoallylic carbamates were generally unsuccessful and resulted instead in relatively inefficient 6-exo cyclisations involving the carbamate carbonyl group. Deiodination provides both trans- and cis-2,5-disubstituted pyrrolidines [49 and 50]; the free amine derived from trans-2-butyl-5-pentylpyrrolidine 49d is a component of a fire ant defence pheromone. X-Ray crystallography was carried out for 37f, 36, and 37k.

  在碳酸钾存在下，(E)-高烯丙基磺酰胺24的5-endo-trig碘环化反应能够高产率地得到反式-2,5-二取代-3-碘吡咯烷36。在没有碱的情况下，这些初始动力学产物通过开环-重闭环机制迅速异构化为相应的顺式-2,5-二取代吡咯烷37，转变为这些热力学异构体。八氢吲哚衍生物40和41也可以从烯丙基环己基磺酰胺31和32得到。高烯丙基氨基甲酸酯的5-endo-trig环化反应尝试一般都不成功，反而导致了氨基甲酸酯羰基参与的相对低效的6-exo环化反应。脱碘反应可以得到反式和顺式-2,5-二取代吡咯烷[49和50]；来源于反式-2-丁基-5-戊基吡咯烷49d的游离胺是火蚁防御信息素的一个组成部分。对37f、36和37k进行了X射线晶体学分析。
• Kamezawa, Makoto; Raku, Takao; Tachibana, Hojun, Bioscience, Biotechnology and Biochemistry, 1995, vol. 59, # 3, p. 549 - 551
  作者：Kamezawa, Makoto、Raku, Takao、Tachibana, Hojun、Ohtani, Takehiko、Naoshima, Yoshinobu

  DOI：——

  日期：——
• Iodoetherification of homoallylic alcohols : A stereoselective approach to tetrahydrofurans
  作者：Simon B. Bedford、Kathryn E. Bell、Garry Fenton、Christopher J. Hayes、David W. Knight、Duncan Shaw

  DOI：10.1016/s0040-4039(00)79029-0

  日期：1992.10

  Iodoetherification of homoallylic alcohols proceeds efficiently and with high levels of stereoselection by a 5-endo-trig process when anhydrous acetonitrile is used as the solvent.
• Tunable, Chemoselective Amination <i>via</i> Silver Catalysis
  作者：Jared W. Rigoli、Cale D. Weatherly、Juliet M. Alderson、Brian T. Vo、Jennifer M. Schomaker

  DOI：10.1021/ja406654y

  日期：2013.11.20

  Organic N-containing compounds, including amines, are essential components of many biologically and pharmaceutically important molecules. One strategy for introducing nitrogen into substrates with multiple reactive bonds is to insert a monovalent N fragment (nitrene or nitrenoid) into a C H bond or add it directly to a C=C bond. However, it has been challenging to develop well-defined catalysts capable of promoting predictable and chemoselective aminations solely through reagent control. Herein, we report remarkable chemoselective aminations that employ a single metal (Ag) and a single ligand (phenanthroline) to promote either aziridination or C H insertion by manipulating the coordination geometry of the active catalysts.
• A new, highly stereoselective approach to pyrrolidines via overall 5-endo-trig cyclisations of homoallylic tosylamides
  作者：Andrew D. Jones、David W. Knight

  DOI：10.1039/cc9960000915

  日期：——

  Iodocyclisations of E-homoallylic tosylamides 7 lead to excellent yields of either 2,5-trans-or 2,5-cis-3-iodopyrrolidines (10 or 11), depending upon the reaction conditions.

  E-高烯丙基对甲苯磺酰胺 7 的碘环化反应，根据反应条件的不同，分别以优异的产率生成 2,5-反式或 2,5-顺式-3-碘吡咯烷（10 或 11）。