3-Undecen-1-ol | 32970-49-3

• 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: 3-Undecen-1-ol
• 英文别名: Undec-3-en-1-ol
• CAS: 32970-49-3
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: UKRXSDKQJLHHDN-UHFFFAOYSA-N

物化性质

• 熔点：
  6.15°C (estimate)
• 沸点：
  264.96°C (estimate)
• 密度：
  0.8629 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  3-Undecen-1-ol 在 正丁基锂 、 pyridinium chlorochromate 作用下， 生成 Tetradeca-3,6-dien-1-ol
  参考文献：
  名称：

  Investigation of aliphatic dienes by chemical ionization with nitric oxide

  摘要：

  AbstractIt is shown that the position of the double bond close to the hydrocarbon end of an aliphatic diene functionalized at C(1) can readily be determined by chemical ionization with NO+. Owing to the low abundance of the ions characteristic for the position of the other double bond, its localization may be difficult. Measurement of the chemical ionization (nitric oxide as reagent gas) spectra of the corresponding epoxides or collision activation studies can help.

  DOI：

  10.1002/oms.1210261205
• 作为产物：
  描述：

  methyl undec-3-enoate 在 lithium aluminium tetrahydride 作用下， 生成 3-Undecen-1-ol
  参考文献：
  名称：

  Hydroboration and thermal isomerization of unsaturated alcohols

  摘要：

  DOI：

  10.1021/jo00970a014

文献信息

• A highly stereoselective synthesis of Z-disubstituted olefin by O-assisted Still-Wittig rearrangement
  作者：Kazushige Fujii、Osamu Hara、Yoko Fujita、Youji Sakagami

  DOI：10.1016/0040-4039(95)02183-3

  日期：1996.1

  In the Still-Wittig rearrangement, stannylated methyl (E)-allylic ethers having an aliphatic side chain (1a-c) exhibited the usual similar stereoselectivity, although the poor stereoselectivity was remarkably improved by the assistance of an alkoxy moiety on the alkenyl chain. A stannylated methyl (Z)-allylic ether bearing an alkoxy moiety on the alkenyl chain (1e) also showed a high E selectivity

  在Still-Wittig重排中，具有脂族侧链（1a-c）的苯乙烯基甲基（E）-烯丙基醚表现出通常相似的立体选择性，尽管不良的立体选择性通过烯基链上的烷氧基部分得到了显着改善。如先前报道的，在烯基链（1e）上带有烷氧基部分的甲氧基化甲基（Z）-烯丙基醚也显示出高的E选择性。
• Nickel-Catalyzed Isomerization/Allylic Cyanation of Alkenyl Alcohols
  作者：Ying Ding、Jinguo Long、Feilong Sun、Xianjie Fang

  DOI：10.1021/acs.orglett.1c02143

  日期：2021.8.6

  Herein reported is a nickel-catalyzed isomerization/allylic cyanation of alkenyl alcohols, which complements current methods for the allylic substitution reactions. The specific diphosphite ligand and methanol as the solvent are crucial for the success for this transformation. A gram-scale regioconvergent experiment and formal synthesis of quebrachamine demonstrate the high potential of this methodology

  本文报道了烯醇的镍催化异构化/烯丙基氰化，它补充了当前用于烯丙基取代反应的方法。特定的二亚磷酸酯配体和作为溶剂的甲醇对于这种转化的成功至关重要。克级区域会聚实验和 quebrachamine 的正式合成证明了这种方法的巨大潜力。
• [2,3]-Wittig rearrangement by a chlorine–lithium exchange
  作者：Beatriz Maciá、Cecilia Gómez、Miguel Yus

  DOI：10.1016/j.tetlet.2005.06.160

  日期：2005.9

  reaction of different allylic chloromethyl ethers 1 with an excess of lithium powder (1:7 molar ratio) and a catalytic amount of DTBB (2.5 mol %) in THF at 0 °C for 1 h gives, after hydrolysis with water, the expected alcohols 2 resulting from a [2,3]-Wittig rearrangement, in an exclusive manner. The same process can also be applied to the corresponding [1,2]-Wittig rearrangement, as it is exemplified

  不同的烯丙基氯甲基醚1与过量的锂粉（摩尔比为1：7）和催化量的DTBB（2.5 mol％）在THF中的反应在0°C下反应1 h，在用水水解后，得到预期的[2,3] -Wittig重排产生的唯一醇2。如对苄基氯甲基醚所举例说明的，相同的方法也可用于相应的[1,2]-维蒂希重排。
• Reversibility of a witting intermediate derived from a triphenylphosphonium ylide and an aliphatic aldehyde
  作者：Allen B. Reitz、Bruce E. Maryanoff

  DOI：10.1039/c39840001548

  日期：——

  Wittig-reaction intermediates derives from hexanal and (γ-oxidopropylidene)triphenylphosphorane, (1), are freely reversible, as indicated by significant quantities of cross-over products from a second aldehyde (octanal): such a result may account for anomalously enhanced E stereoselectivity in the reaction of γ- and β-oxido ylieds with aliphatic aldehydes.

  Wittig反应中间体衍生自己醛和（γ-氧化亚丙基）三苯基磷烷（1），可自由逆转，如大量的第二醛（辛醛）交叉产物所表明：这样的结果可能解释了E异常增强的原因。γ-和β-氧化烯类化合物与脂肪族醛的反应中的立体选择性。