十一碳-1,2-二烯-4-醇 | 79090-73-6

• 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: 十一碳-1,2-二烯-4-醇
• 英文名称: undeca-1,2-dien-4-ol
• 英文别名: 1,2-undecadien-4-ol
• CAS: 79090-73-6
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: RKAQZCYXAFHXCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  十一碳-1,2-二烯-4-醇 在 吡啶 、 palladium diacetate 、 lithium bromide 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 生成 (3E)-2-bromo-1,3-undecadiene
  参考文献：
  名称：

  Palladium(II)-Catalyzed S_N2‘ Reactions of α-Allenic Acetates. Stereoconvergent Synthesis of (Z,E)-2-Bromo-1,3-dienes

  摘要：

  The reaction of acetylated a-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)(2) provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.

  DOI：

  10.1021/jo015950x
• 作为产物：
  描述：

  1-(Tetrahydro-pyran-2-yloxy)-undec-2-yn-4-ol 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以7.13 g的产率得到十一碳-1,2-二烯-4-醇
  参考文献：
  名称：

  Palladium(II)-Catalyzed S_N2‘ Reactions of α-Allenic Acetates. Stereoconvergent Synthesis of (Z,E)-2-Bromo-1,3-dienes

  摘要：

  The reaction of acetylated a-allenic alcohols with LiBr in the presence of 1.5 mol % of Pd(OAc)(2) provides easy access to substituted (Z,E)-2-bromo-1,3-dienes in good yields with excellent diastereoselectivity. Both secondary and tertiary acetates as well as terminal and nonterminal allenes were studied to investigate the scope and the limitations of the reaction. A mechanism is proposed to clarify how a diastereomeric mixture of the starting compound is transformed into a single diastereomer of the product.

  DOI：

  10.1021/jo015950x

文献信息

• Highly stereoselective kinetic resolution of α-allenic alcohols: an enzymatic approach
  作者：Wenhua Li、Zuming Lin、Long Chen、Xuechao Tian、Yan Wang、Sha-Hua Huang、Ran Hong

  DOI：10.1016/j.tetlet.2015.12.098

  日期：2016.2

  A highly efficient lipase AK-catalyzed direct kinetic resolution of a variety of α-allenic alcohols was developed. With the complementary to previous studies, the current reaction system is effective on a broad range of substituents (R1) at C(1), such as alkyl, aryl, alkenyl, and alkynyl groups. The Jones–Burgess empirical model was modified to interpret the reversed selectivity during the acetylation

  开发了一种高效脂肪酶AK催化的多种α-烯醇的直接动力学拆分方法。作为对先前研究的补充，当前的反应系统对C（1）上的广泛取代基（R 1）有效，例如烷基，芳基，烯基和炔基。修改了Jones-Burgess的经验模型，以解释仲醇乙酰化过程中逆向选择性。烯丙醇的C（2）处的甲基暗示脂肪酶AK的催化三联体中的小结构调整，代表未来定点诱变的潜在方向。
• Efficient Synthesis of 3-Chloromethyl-2(5<i>H</i>)-furanones and 3-Chloromethyl- 5,6-dihydropyran-2-ones via the PdCl₂-Catalyzed Chlorocyclocarbonylation of 2,3- or 3,4-Allenols
  作者：Xin Cheng、Xuefeng Jiang、Yihua Yu、Shengming Ma

  DOI：10.1021/jo8015677

  日期：2008.11.21

  was formed between the center carbon atom of the allene moiety and the hydroxyl oxygen, which was established by the X-ray single crystal diffraction study of gamma-lactone 3p. The highly optically active 3-chloromethyl-2(5H)-furanones could be easily prepared from the readily available optically active 2,3-allenols. A mechanism for this reaction was proposed.

  一种温和有效的方法，涉及PdCl2催化的2,3或3,4-烯丙醇与CuCl2的氯环羰基化反应，用于合成3-氯甲基-2（5H）-呋喃酮和3-氯甲基-5,6-二氢吡喃-2-的开发。该反应以高度区域选择性的方式进行，即，将氯原子引入到丙二烯部分的末端位置，而在内酯键的中心碳原子与由X建立的羟基氧之间形成内酯键。内酯3p的X射线单晶衍射研究。高光学活性的3-氯甲基-2（5H）-呋喃酮可以容易地由容易获得的光学活性的2，3-烯醇制备。提出了该反应的机制。
• A General Approach to Terminal Allenols
  作者：Shengming Ma、Jinqiang Kuang、Xi Xie

  DOI：10.1055/s-0032-1317949

  日期：——

  demonstrated a very general method for the preparation of essentially any terminal 2,3-allenol from the corresponding alkynols, which may be easily available from propargylic alcohols by alkylation, or from terminal alkynes by deprotonation and 1,2-addition with aldehydes or ketones, and subsequent base-catalyzed triple-bond migration. We have demonstrated a very general method for the preparation of essentially

  摘要 我们已经证明了一种非常通用的方法，可以从相应的炔醇制备基本上任何末端的2,3-丙烯醇，可以很容易地从炔丙醇中通过烷基化获得，也可以从末端炔烃中通过去质子化和与醛的1,2-加成反应轻松获得。酮，以及随后的碱催化的三键迁移。 我们已经证明了一种非常通用的方法，可以从相应的炔醇制备基本上任何末端的2,3-丙烯醇，可以很容易地从炔丙醇中通过烷基化获得，也可以从末端炔烃中通过去质子化和与醛的1,2-加成反应轻松获得。酮，以及随后的碱催化的三键迁移。
• CuI-Catalyzed Synthesis of Functionalized Terminal Allenes from 1-Alkynes
  作者：Hongwen Luo、Shengming Ma

  DOI：10.1002/ejoc.201201696

  日期：2013.5

  equiv.), a facile and efficient protocol for the gram-scale synthesis of functionalized terminal allenes by using CuI (7.5–10 mol-%), paraformaldehyde (1.6 equiv.), and diisopropylamine (1.4 equiv.) has been developed. This method accommodates different functional groups such as hydroxy or carbonyl, and it also performed well in the synthesis of allenylamides and 2,3-butadien-1-ol.

  相对于我们使用 CuI（0.5 当量）、多聚甲醛（2.5 当量）和二环己胺（1.8 当量）的原始方案，这是一种使用 CuI（7.5– 10 mol-%)、多聚甲醛（1.6 当量）和二异丙胺（1.4 当量）已被开发。该方法适应不同的官能团，如羟基或羰基，在合成丙二烯酰胺和2,3-丁二烯-1-醇方面也表现良好。
• Barbier-type allylation of carbonyl compounds and imines with metallic cadmium
  作者：Bir Sain、Dipak Prajapati、Jagir S Sandhu

  DOI：10.1016/s0040-4039(00)61288-1

  日期：1992.8

  Cadmium mediated allylation of a variety of carbonyl compounds and imines in a Cd/Bu4NBr/THF system afforded excellent yields of the corresponding homoallylic alcohols and amines under very mild reaction conditions.

  在Cd / Bu 4 NBr / THF系统中，镉介导的各种羰基化合物和亚胺的烯丙基化在非常温和的反应条件下提供了极佳的相应均烯丙基醇和胺收率。