(E)-十一碳-1,5-二烯-3-醇 | 107172-51-0

• 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)-十一碳-1,5-二烯-3-醇
• 英文名称: (E)-undeca-1,5-dien-3-ol
• 英文别名: (E)-1,5-undecadien-3-ol；3-hydroxy-undeca-1,5cis-diene；Undeca-1,5-dien-3-ol；(5E)-undeca-1,5-dien-3-ol
• CAS: 107172-51-0
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: JYWXEBALSPBIIA-CMDGGOBGSA-N

物化性质

• 沸点：
  246.5±9.0 °C(Predicted)
• 密度：
  0.855±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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)-十一碳-1,5-二烯-3-醇 以87%的产率得到(E,E) ethyl 4,7-tridecadienoate
  参考文献：
  名称：

  基于双烯丙基醚系统[2,3] -wittig重排的新σ序列：导致不饱和羰基化合物的烯丙基部分区域控制的cc键形成的一般方法

  摘要：

  描述了由不对称双烯丙基醚（1）到1,5-二烯-3-醇（2）的区域控制[2,3] -Wittig重排触发的四个新的sigmatropic序列，它们提供了独特的区域控制方法具有令人感兴趣的分子框架的各种不饱和羰基化合物的合成。新开发的序列包括[2,3] -Wittig-Claisen，串联[2,3] -Wittig-oxy-Cope，串联oxy-Cope-Claisen和串联oxy-Cope-Cope序列。

  DOI：

  10.1016/s0040-4020(01)90580-0
• 作为产物：
  描述：

  1-辛烯-3-醇 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 21.25h， 生成 (E)-十一碳-1,5-二烯-3-醇
  参考文献：
  名称：

  Crawley, John E.; Kaye, Aston D.; Pattenden, Gerald, Journal of the Chemical Society. Perkin transactions I, 1993, # 17, p. 2001 - 2008

  摘要：

  DOI：

文献信息

• Process for the preparation of poly-unsaturated hydrocarbons
  申请人：Firmenich S.A.

  公开号：US03960977A1

  公开（公告）日：1976-06-01

  Process for the preparation of poly-unsaturated hydrocarbons, in particular undeca-1,3,5-triene, which comprises reacting a quaternary phosphonium salt with hexanal. The product obtained in accordance with the process of the invention is a useful perfuming ingredient.

  制备多不饱和碳氢化合物的过程，特别是十一烯-1,3,5的制备方法，包括将季铵磷盐与己醛反应。根据本发明的方法得到的产品是一种有用的香料成分。
• Stereoselective synthesis of -disubstituted olefins via 2,3-sigmatropic rearrangements. An approach to leukotrienes.
  作者：Aston D Kaye、Gerald Pattenden、Stanley M Roberts

  DOI：10.1016/s0040-4039(00)84441-x

  日期：1986.1

  Stereoselective 2,3-sigmatropic rearrangement of the propargyl 2-silylallyl ether(5) leads to the vinyl silane (7), which, after protiodesilylation and palladium catalysed coupling to 3-bromoprop-2-enol, produces the ,-dienynol (10) a key intermediate in leukotriene synthesis.

  炔丙基2- silylallyl醚的立体选择性2,3-σ重排（5）通向乙烯基硅烷（7），其protiodesilylation和钯后催化的偶联到3-溴-2-烯醇，产生，-dienynol（10 ）白三烯合成中的关键中间体。
• SEQUENTIAL [2,3]WITTIG AND CLAISEN REARRANGEMENT: A FACILE SYNTHETIC METHOD FOR (<i>E</i>,<i>E</i>)-4,7-ALKADIENALS AND -ALKADIENOIC ACIDS. A NEW FORMAL SYNTHESIS OF (±)-CERULENIN
  作者：Koichi Mikami、Naoyuki Kishi、Takeshi Nakai

  DOI：10.1246/cl.1981.1721

  日期：1981.12.5

  The regioselective [2,3]Wittig rearrangement of bis-allylic ethers followed by the Claisen rearragement permits ready access to (E,E)-4,7-alkadienals and -alkadienoic acids. The versatility of the sigmatropic sequence is demonstrated within the context of a new formal synthesis of (±)-cerulenin possessing an interesting spectrum of biological activities.

  双烯丙基醚的亲区选择性[2,3]Wittig重排，以及随后的Claisen重排，可以方便地得到（E,E）-4,7-烯丙二烯醛和烯丙二烯酸。在具有多种生物活性的（±）-青霉烯素的新形式合成中，展示了西格马拓扑序列的多功能性。
• Influence of the Chemical Structure on Odor Qualities and Odor Thresholds in Homologous Series of Alka-1,5-dien-3-ones, Alk-1-en-3-ones, Alka-1,5-dien-3-ols, and Alk-1-en-3-ols
  作者：Katja Lorber、Peter Schieberle、Andrea Buettner

  DOI：10.1021/jf404885j

  日期：2014.2.5

  Odor qualities and odor thresholds in air in homologous series of synthesized alk-1-en-3-ols and alka-1,5-dien-3-ols and their corresponding ketones were evaluated by gas chromatography-olfactometry. In the series of the alk-1-en-3-ols and alk-1-en-3-ones the odor quality changed successively from pungent for the compounds with five carbon atoms via metallic, vegetable-like for the six- and seven-carbon odorants to mushroom-like for the compounds with eight and nine carbon atoms. With further increase in chain length the mushroom-like impression decreased and changed to citrus-like, soapy, or herb-like. In both series, two odor threshold minima were found for the six-carbon and also for the eight- and nine-carbon odorants, respectively. In contrast to this, the odor qualities in the series of the (Z)- and (E)-alka-1,5-dien-3-ols and their corresponding ketones did not change significantly with geranium-like, metallic odors and an increasing mushroom-like odor note with increasing chain length. The lowest thresholds were found for the eight- and nine-carbon (Z)-compounds, respectively.
• Servi, Sueleyman; Ahmedzade, Misir; Coskun, Mehmet, South African Journal of Chemistry, 2000, vol. 53, # 2, p. 73 - 76
  作者：Servi, Sueleyman、Ahmedzade, Misir、Coskun, Mehmet、Cansiz, Ahmet

  DOI：——

  日期：——