(5Z)-1,5-undecadien-3-ol | 56722-23-7

• 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: (5Z)-1,5-undecadien-3-ol
• 英文别名: (Z)-undeca-1,5-dien-3-ol；1,cis-5-undecadien-3-ol；rac-1,5-undecadien-3-ol；undeca-1,5(Z)-dien-3-ol；1,5Z-undecadien-3-ol；1,5-undecadien-3-ol；(5Z)-undeca-1,5-dien-3-ol
• CAS: 56722-23-7
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: JYWXEBALSPBIIA-HJWRWDBZSA-N

物化性质

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

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

安全信息

• 海关编码：
  2905290000

反应信息

• 作为反应物：
  描述：

  (5Z)-1,5-undecadien-3-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以41%的产率得到(Z)-undeca-1,5-dien-3-one
  参考文献：
  名称：

  （±）-dictyopterene A（一种从褐色海藻中获得的有味物质）的生物遗传类型合成，

  摘要：

  （±）-dictyopterene A（）的生物遗传型合成通过使用1，-5-undecadien-3-ol（）被假定为的生物合成中间体而实现：该合成意味着dictyoprolene（）转化为dictyopterene A（）。是正式制作的。

  DOI：

  10.1016/0040-4039(80)80163-8
• 作为产物：
  描述：

  1-庚炔 在 sodium tetrahydroborate 、 正丁基锂 、 水 、 氢气 、 nickel diacetate 、 草酸 、 乙二胺 作用下， 以 乙醚 、 乙醇 、 丙酮 为溶剂， 反应 2.75h， 生成 (5Z)-1,5-undecadien-3-ol
  参考文献：
  名称：

  Nonshita, Katsumasa; Banno, Hiroshi; Maruoka, Keiji, Journal of the American Chemical Society, 1990, vol. 112, # 1, p. 316 - 322

  摘要：

  DOI：

文献信息

• A simple synthesis of 4E,7Z-tridecadien-1-yl acetate, a component of the sex pheromone of the potato mothPhtorimaea operculella (Lepidoptera:Gelehiidae)
  作者：A. A. Vasil'ev、E. P. Serebryakov

  DOI：10.1007/bf01430748

  日期：1996.9

  double bonds is ≥95%. TheZ configuration of the Δ7 bond results from the 1,4-cis-hydrogenation of the intermediate 1,4,6-undecatrien-3-ol in the presence of an (arene)chromium tricarbonyl complex, while theE configuration of the Δ4 bond arises in the Claisen-Johnson rearrangement occuring in the reaction of 1,5Z-undecadien-3-ol with trimethyl orthoacetate.

  从市售的 2,4-壬二烯醛开始，对标题化合物进行了简单的五步合成。信息素总收率为29%，Δ4和Δ7双键的几何纯度≥95%。Δ7 键的 Z 构型是由中间体 1,4,6-十一碳三烯-3-醇在（芳烃）三羰基铬配合物存在下的 1,4-顺式氢化产生的，而 Δ4 键的 E 构型产生在 1,5Z-undecadien-3-ol 与原乙酸三甲酯反应中发生的 Claisen-Johnson 重排。
• 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.
• Chemo-enzymatic enantio-convergent asymmetric total synthesis of (S)-(+)-dictyoprolene using a kinetic resolution—stereoinversion protocol
  作者：Andreas Wallner、Harald Mang、Silvia M. Glueck、Andreas Steinreiber、Sandra F. Mayer、Kurt Faber

  DOI：10.1016/s0957-4166(03)00481-6

  日期：2003.8

  A single enantiomer of a (stereo)chemically labile allylic-homoallylic alcohol was obtained in 91% e.e. and 96% yield from the racemate by employing a lipase-catalysed kinetic resolution coupled to in situ inversion under carefully controlled (Mitsunobu) conditions in order to Suppress side reactions, such as elimination and racemisation. This technique was Successfully applied to an enantio-convergent asymmetric total synthesis of the algal fragrance component (S)-dictyoprolene. (C) 2003 Elsevier Ltd. All rights reserved.
• Vig, O. P.; Kad, G. L.; Sabharwal, Arun, Journal of the Indian Chemical Society, 1989, vol. 66, p. 28 - 29
  作者：Vig, O. P.、Kad, G. L.、Sabharwal, Arun、Sharma, Sanjiv、Dogra, Vijay

  DOI：——

  日期：——
• Chattopadhyay, A.; Mamdapur, V. R.; Chadha, M. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 187 - 188
  作者：Chattopadhyay, A.、Mamdapur, V. R.、Chadha, M. S.

  DOI：——

  日期：——