(E)-dodec-3-en-2-ol | 93425-53-7

• 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: (E)-dodec-3-en-2-ol
• 英文别名: (E)-3-dodecen-2-ol
• CAS: 93425-53-7
• 化学式: C₁₂H₂₄O
• 分子量: 184.322
• InChiKey: FBKPUBDLPJUNKZ-ZHACJKMWSA-N

物化性质

• 沸点：
  249.6±8.0 °C(Predicted)
• 密度：
  0.845±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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)-dodec-3-en-2-ol 以22%的产率得到(S)-(-)-(E)-3-dodecen-2-ol
  参考文献：
  名称：

  Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp

  摘要：

  Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of beta-hydroxy-alpha-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of gamma-hydroxy-alpha,beta-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.

  DOI：

  10.1021/ja00016a032
• 作为产物：
  描述：

  dodec-3-yn-2-ol 在 氨 、 sodium 作用下， 生成 (E)-dodec-3-en-2-ol
  参考文献：
  名称：

  Studies on PPL Catalyzed Acetylation of 2-Alkanols: Its Application for the Synthesis of 2-Dodecanol and 2-Tridecyl Acetate, the Pheromones ofCrematogasterAnts andDrosophila mulleriFlies

  摘要：

  Several aliphatic 2-alkanols with varying chain length has been efficiently resolved by their acetylation using vinyl acetate/PPL in diisopropyl ether. The effect of solvent polarity, position and type of unsaturation and chain length has been probed. This has led to more convenient synthesis of some insect pheromones.

  DOI：

  10.1080/00397919608003858

文献信息

• Studies on the Cu(I)-Catalyzed Regioselective <i>anti</i>-Carbometallation of Secondary Terminal Propargylic Alcohols
  作者：Zhan Lu、Shengming Ma

  DOI：10.1021/jo0524021

  日期：2006.3.31

  A highly regioselective Cu(I)-catalyzed anti-carbometallation of secondary terminal propargylic alcohols with 1° alkyl or aryl Grignard reagents affording 2-substituted allylic alcohols was developed. By using this method, optically active allylic alcohols can be prepared from the optically active propargylic alcohols without obvious loss of the enantiopurity. The cyclic organometallic intermediate

  开发了高度区域选择性的Cu（I）催化的仲末端炔丙基醇与提供2个取代的烯丙基醇的1°烷基或芳基格氏试剂的抗碳金属化反应。通过使用该方法，可以从旋光的炔丙醇制备旋光的烯丙醇而对映体纯度没有明显的损失。形成的环状有机金属中间体可以进行碘化反应或Pd（0）催化的偶联反应，得到立体定义的烯丙基醇。
• Convergent synthesis of conjugated 1,2-disubstituted E-allylic alcohols from two aldehydes and methylenetriphenylphosphorane
  作者：David M. Hodgson、Rosanne S. D. Persaud

  DOI：10.1039/c2ob26346g

  日期：——

  β-Lithiooxyphosphonium ylides, made in situ from an aldehyde and methylenetriphenylphosphorane, react with a second aldehyde to form E-allylic alcohols. α-Branching and α,β-unsaturation in the second aldehyde, together with the lack of further substitution on the phosphorane carbon play important roles in selectivity. A range of these aldehydes, in addition to aromatic aldehydes as the second aldehyde also provided synthetically useful access to E-allylic alcohols.

  第二醛中α-支化和α,β-不饱和以及磷烷碳上缺乏进一步的取代在选择性方面起着重要作用。除了以芳香醛作为第二醛外，这些醛还提供了合成 E-烯丙基醇的有用途径。
• DOOLITTLE, R. E.;HEATH, R. R., J. ORG. CHEM., 1984, 49, N 26, 5041-5050
  作者：DOOLITTLE, R. E.、HEATH, R. R.

  DOI：——

  日期：——
• Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp
  作者：Kevin Burgess、Lee D. Jennings

  DOI：10.1021/ja00016a032

  日期：1991.7

  Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of beta-hydroxy-alpha-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of gamma-hydroxy-alpha,beta-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.
• Studies on PPL Catalyzed Acetylation of 2-Alkanols: Its Application for the Synthesis of 2-Dodecanol and 2-Tridecyl Acetate, the Pheromones of<i>Crematogaster</i>Ants and<i>Drosophila mulleri</i>Flies
  作者：Anubha Sharma、Archana S. Pawar、Subrata Chattopadhyay

  DOI：10.1080/00397919608003858

  日期：1996.1

  Several aliphatic 2-alkanols with varying chain length has been efficiently resolved by their acetylation using vinyl acetate/PPL in diisopropyl ether. The effect of solvent polarity, position and type of unsaturation and chain length has been probed. This has led to more convenient synthesis of some insect pheromones.