3-甲基-1-十二炔-3-醇 | 24424-78-0

• 物质功能分类: 化学试剂 - 有机试剂 - 炔烃
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-甲基-1-十二炔-3-醇
• 英文名称: 3-methyldodec-1-yn-3-ol
• 英文别名: 3-methyl-1-dodecyn-3-ol
• CAS: 24424-78-0
• 化学式: C₁₃H₂₄O
• mdl: MFCD00041583
• 分子量: 196.333
• InChiKey: INASARODRJUTTN-UHFFFAOYSA-N

物化性质

• 沸点：
  119-120°C 7mm
• 密度：
  0,84 g/cm3
• 闪点：
  119-120°C/7mm
• 稳定性/保质期：

  如果遵照规格使用和储存，则不会分解。避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.846
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25,S26,S36/37/39
• 危险类别码：
  R20/21,R36/37/38
• 海关编码：
  2905290000

制备方法与用途

应用广泛，3-甲基-1-十二炔-3-醇可用作有机合成中间体及医药中间体，在实验室研发和医药化工生产中发挥重要作用。

反应信息

• 作为反应物：
  描述：

  3-甲基-1-十二炔-3-醇 在 氢溴酸 、 铜 、 copper(I) bromide 作用下， 以 正戊烷 为溶剂， 生成
  参考文献：
  名称：

  Designed Bifunctional Phosphine Ligand-Enabled Gold-Catalyzed Isomerizations of Ynamides and Allenamides: Stereoselective and Regioselective Formation of 1-Amido-1,3-dienes

  摘要：

  By using designed biphenyl-2-ylphosphines functionalized with a remote basic groups as ligands, N-alkynyl-o-nosylamides are directly converted to (1E,3E)-1-amido-1,3-dienes with excellent diastereoselectivities under gold catalysis. With allenamides as substrates, the gold-catalyzed isomerizations are high yielding and applicable to a broad substrate scope including various nitrogen protecting groups and exhibit unprecedented (3E)-selectivities for the distal C-C double bond and good regioselectivities. Combining this gold catalysis with one-pot Diels-Alder reactions leads to rapid assembly of valuable bicyclic compounds.

  DOI：

  10.1021/acs.orglett.7b02624
• 作为产物：
  描述：

  2-十一酮 在 乙醚 、 sodium amide 作用下， 生成 3-甲基-1-十二炔-3-醇
  参考文献：
  名称：

  Comparative phytotoxicity of four monoterpenes against Cassia occidentalis

  摘要：

  SummaryThe effect of four monoterpenes ‐ citronellol, citronellal, cineole and linalool ‐ on the germination, growth and physiology of Cassia occidentalis was investigated. All four monoterpenes reduced germination of C. occidentalis seeds but to varying extents. Citronellal and linalool completely inhibited germination beyond the concentrations of 55 and 110 μM, respectively, whereas in response to treatment of citronellol no germination was observed beyond 330 μM. Further, the growth of seedlings, measured in terms of seedling length and biomass, was also adversely affected. A reduction in chlorophyll content of the cotyledonary leaves of C. occidentalis was also noticed, indicating an adverse effect on photosynthesis. Likewise, respiratory ability of growing seeds was also impaired in response to all four monoterpenes, clearly indicating that monoterpenes affect energy metabolism. On the basis of overall phytotoxicity, potency of monoterpenes was in the order of citronellal > linalool > citronellol > cineole. The results from this study suggest that both citronellal and linalool possess strong phytotoxic potential and can thus serve as lead molecules for the synthesis of bioherbicides.

  DOI：

  10.1111/j.1744-7348.2002.tb00202.x

文献信息

• 一种偕-1,3-烯炔类化合物的合成方法
  申请人：湖南第一师范学院

  公开号：CN113354511B

  公开（公告）日：2022-03-25

  本发明提供了一种钯/四甲基乙二胺催化炔醇衍生物与芳香炔烃类化合物交叉二聚合成偕‑1,3‑烯炔类化合物的方法。该方法催化剂和配体简单、廉价、易得，具有立体、区域和化学选择性高、官能团兼容性好、所得目标产物易分离、反应操作简便、安全可靠等特点。该方法主要解决了其它方法需要复杂、昂贵的配体和金属催化剂问题，很好地解决了两种不同炔烃不易高选择性交叉二聚的难题，具有重要的科学意义和合成应用价值。
• Gold(<scp>i</scp>) “click” 1,2,3-triazolylidenes: synthesis, self-assembly and catalysis
  作者：Kelly J. Kilpin、Ursula S. D. Paul、Ai-Lan Lee、James D. Crowley

  DOI：10.1039/c0cc02185g

  日期：——

  Novel gold(I) “click” carbene(1,2,3-triazolylidene) complexes have been synthesised, characterised and exploited for the self-assembly of a metallomacrocycle and as precatalysts for gold(I)-catalysed reactions.

  新型金(I)配合物——“点击”卡宾（1,2,3-三唑亚基）——已被合成、表征，并用于金属大环的自组装以及作为金(I)催化反应的前催化剂。
• A dual-functional urea-linked conjugated porous polymer anchoring silver nanoparticles for highly efficient CO₂ conversion under mild conditions
  作者：Xiaoji Wang、Wang Li、Jianxin Wang、Jie Zhu、Yuting Li、Xiaozhen Liu、Liping Wang、Lin Li

  DOI：10.1039/d0dt02559c

  日期：——

  cyclization of propargyl alcohols with CO2 under mild conditions, together with good recyclability, which is probably attributed to the synergistic effect of the UCPP on the adsorption and activation of CO2 and the immobilization of Ag nanoparticles. This work affords possible opportunities for the design and synthesis of a heterogeneous catalyst toward CO2 conversion.

  制备了由烯醇-亚胺组装的双功能脲键合共轭多孔聚合物（UCPP），其中有序单元阵列充当网络中潜在的锚固位点，并通过它们之间的配位相互作用而进一步用作银纳米颗粒的载体。UCPP不仅可以很好地限制Ag的粒径并促进高分散性，而且可以提供特殊的亲CO 2部分以增强吸附性能。所得的Ag @ UCPP作为非均相催化剂在温和条件下对炔丙基醇与CO 2的羧基环化表现出优异的活性，并具有良好的可回收性，这可能归因于UCPP对CO 2的吸附和活化具有协同作用。和银纳米粒子的固定化。这项工作为多相催化剂向CO 2转化的设计和合成提供了可能的机会。
• New Entry to Polycyclic Fused Indoles via Gold(I)-catalyzed Cascade Reaction
  作者：Michel Chiarucci、Elia Matteucci、Gianpiero Cera、Giancarlo Fabrizi、Marco Bandini

  DOI：10.1002/asia.201201249

  日期：2013.8

  The gold standard: A gold‐catalyzed cascade reaction sequence for the preparation of polycyclic fused indole cores exploits the ready availability and chemical flexibility of propargylic alcohols. The desired tri‐ or tetracyclic compounds are obtained in good yields with water as the only stoichiometric by‐product.

  金标准：用于制备多环稠合吲哚核的金催化级联反应序列利用了炔丙醇的易得性和化学灵活性。用水作为唯一的化学计量副产物，可以高收率获得所需的三环或四环化合物。
• METHOD OF HYDROSILYLATION IMPLEMENTING AN ORGANIC CATALYST DERIVED FROM GERMYLENE
  申请人：BLUESTAR SILICONES FRANCE SAS

  公开号：US20170313729A1

  公开（公告）日：2017-11-02

  The present invention concerns a method for the hydrosilylation of an unsaturated compound comprising at least one ketone function, one aldehyde function, one alkene function and/or one alkyne function, with a compound comprising at least one hydrogen-silyl function implementing an organic catalyst of tri-coordinated germanium.

  本发明涉及一种用于水硅烷基化不饱和化合物的方法，所述不饱和化合物包括至少一个酮基功能、一个醛基功能、一个烯烃功能和/或一个炔烃功能，与至少一个含有氢硅基功能的化合物反应，使用三配位的有机催化剂锗实施。