十二碳-1,2-二烯-4-醇 | 78808-41-0

• 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: 十二碳-1,2-二烯-4-醇
• 英文名称: dodeca-1,2-dien-4-ol
• CAS: 78808-41-0
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: WEUPPAJYFCIQAM-UHFFFAOYSA-N

物化性质

• 沸点：
  248.3±8.0 °C(Predicted)
• 密度：
  0.835±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  十二碳-1,2-二烯-4-醇 在 邻苯二甲酸二甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 dodeca-1,2-dien-4-one
  参考文献：
  名称：

  Studies on K₂CO₃-Catalyzed 1,4-Addition of 1,2-Allenic Ketones with Diethyl Malonate:  Controlled Selective Synthesis of β,γ-Unsaturated Enones and α-Pyrones

  摘要：

  The K2CO3 (10 mol %)-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones leading to polyfunctionalized beta,gamma-unsaturated enones 3 or 4 was studied. With 3-unsubstituted 1-substituted-1,2-allenyl ketones, the highly selective formation of beta,gamma-unsaturated enones 4 was observed; with 1,2-allenyl ketones bearing one or two 3-substituents in the allenyl group, only beta,gamma-unsaturated enones 3 with an immigrated carbon-carbon double bond were produced; with 3-monosubstituted-1,2-allenyl ketones Z-beta,gamma-unsaturated enones 3 were formed with excellent stereoselectivity (E:Z > 96:4); with propadienyl ketones, mixtures of beta,gamma-unsaturated enones 3 and 4 were formed. alpha-Pyrone derivatives were synthesized via the K2CO3-catalyzed or -promoted reaction of 1,2-allenic ketones with diethyl malonate via a sequential Michael addition-carbon-carbon double bond migration-lactonization process.

  DOI：

  10.1021/jo034633i
• 作为产物：
  描述：

  在 potassium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 十二碳-1,2-二烯-4-醇
  参考文献：
  名称：

  Indium-mediated coupling of aldehydes with prop-2-ynyl bromides in aqueous media

  摘要：

  铟介导的醛1与丙-2-炔基溴化物2的耦合反应发生区域选择性，生成同丙-2-炔醇3或烯丙醇4，具体取决于丙-2-炔基溴化物的γ取代基。

  DOI：

  10.1039/c39950001003

文献信息

• 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。
• Catalytic Asymmetric Allenylation of Malonates with the Generation of Central Chirality
  作者：Qiankun Li、Chunling Fu、Shengming Ma

  DOI：10.1002/anie.201204346

  日期：2012.11.19

  Water plays an important role in a palladium‐catalyzed allenylation of diethyl malonate with 2,3‐allenyl acetates to yield centrally chiral allenyl malonates bearing synthetically useful functional groups (see scheme). The products were formed with 92–96 % ee in the presence of a bulky, electron‐rich biphenyl ligand at room temperature.

  水在钯催化的丙二酸二乙酯与2，3-烯丙基乙酸酯的烯丙基化反应中起重要作用，以产生带有合成有用官能团的中心手性烯丙二酸酯（参见方案）。在室温下，在存在大量电子富集的联苯配体的情况下，形成的产品具有92％至96％  ee。
• A CONVENIENT SYNTHESIS OF α-HYDROXYALLENES BY THE REACTION OF PROPARGYL IODIDES WITH ALDEHYDES IN THE PRESENCE OF STANNOUS HALIDE
  作者：Teruaki Mukaiyama、Taira Harada

  DOI：10.1246/cl.1981.621

  日期：1981.5.5

  In the presence of stannous halide, propargyl iodides react with aldehydes in an aprotic solvent to yield α-hydroxyallenes as major products, particularly in the cases of γ-substituted propargyl iodides, along with β-hydroxyacetylenes.

  在卤化亚锡存在下，炔丙基碘与醛在非质子溶剂中反应，生成 α-羟基丙二烯作为主要产物，特别是在 γ-取代的炔丙基碘和 β-羟基乙炔的情况下。
• A practical procedure of propargylation of aldehydes
  作者：Papiya Ghosh、Angshuman Chattopadhyay

  DOI：10.1016/j.tetlet.2012.07.021

  日期：2012.9

  An operationally simple procedure of propargylation of aldehydes in moist solvent (distilled THF) has been developed through direct addition of propargyl bromide to aldehyde substrates mediated with low valent iron or tin. The metals were spontaneously prepared in situ employing bimetal redox strategy. Using different aldehydes as substrates (3a–k) both these metal mediated reactions took place producing

  通过将炔丙基溴直接加到由低价铁或锡介导的醛底物上，已经开发出了一种在湿溶剂（蒸馏的THF）中将醛炔丙基化的操作简单方法。使用双金属氧化还原策略自发地原位制备金属。使用不同的醛作为底物（3a - k），这两种金属介导的反应均发生，在所有情况下均以高收率产生高炔丙基醇（4a - k），并且在大多数情况下具有较高的化学选择性（表1）。由于其功效，操作简便性，在潮湿溶剂中的性能，并且包括使用廉价的金属/金属盐，因此该方法实际上可行并且可能具有可扩展性。
• Pd(0)-Catalyzed Insertion−Cyclization Reaction of 2,3-Allenols with Aryl or Alkenyl Halides. Diastereoselective Synthesis of Highly Optically Active <i>trans</i>-2,3-Disubstituted Vinylic Oxiranes
  作者：Shengming Ma、Shimin Zhao

  DOI：10.1021/ja9904888

  日期：1999.9.1

  Pd(0)-catalyzed insertion-cyclization reaction of 2,3-allenols with aryl or alkenyl halides. Diastereoselective synthesis of highly optically active trans-2,3-disubstituted vinylic oxiranes.

  Pd(0)-催化的 2,3-烯醇与芳基或烯基卤化物的插入-环化反应。高光学活性反式-2,3-二取代乙烯基环氧乙烷的非对映选择性合成。