2-甲基-5-辛炔-4-醇 | 60657-70-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-甲基-5-辛炔-4-醇
• 英文名称: 2-methyl-5-octyne-4-ol
• 英文别名: 2-methyl-5-octyn-4-ol；2-methyloct-5-yn-4-ol
• CAS: 60657-70-7
• 化学式: C₉H₁₆O
• mdl: MFCD00041690
• 分子量: 140.225
• InChiKey: YBGQRUFRRPFNKW-UHFFFAOYSA-N

物化性质

• 密度：
  0,855 g/cm3
• 闪点：
  78°C
• 稳定性/保质期：
  避免接触氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.777
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 安全说明：
  S24/25
• 储存条件：
  在密封的贮藏器中，并将其存放在阴凉、干燥的地方。

反应信息

• 作为反应物：
  描述：

  2-甲基-5-辛炔-4-醇 在 palladium on activated charcoal 咪唑 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 2-甲基-4-辛醇
  参考文献：
  名称：

  Solvent-modulated Pd/C-catalyzed deprotection of silyl ethers and chemoselective hydrogenation

  摘要：

  Recently we have reported undesirable and frequent deprotection of the TBDMS protective group of a variety of hydroxyl functions occurred under neutral and mild hydrogenation conditions using 10% Pd/C in MeOH. The deprotection of silyl ethers is susceptible to significant solvent effect. TBDMS and TES protecting groups were selectively cleaved in the presence of acid-sensitive functional groups such as TIPS ether, TBDPS ether and dimethyl acetal under hydrogenation condition using 10% Pd/C in MeOH. In contrast, chemoselective hydrogenation of reducible functional groups such as acetylene, olefin and benzyl ether, proceeds in the presence of TBDMS or TES ethers in AcOEt or MeCN. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.098

文献信息

• <i>trans</i> ‐Hydroboration of Propargyl Alcohol Derivatives and Related Substrates
  作者：Lauren E. Longobardi、Alois Fürstner

  DOI：10.1002/chem.201902228

  日期：2019.8

  in good to excellent levels of regio‐ as well as stereoselectivity, provided that the triple bond bears one linear and one singly‐branched substituent. In such cases, the reaction follows an unusual trans‐addition mode and places the boron entity distal to the branching point. The resulting alkenyl boronates, which are difficult to make otherwise, can be engaged in numerous enabling downstream processes

  如果三键带有一个直链和一个单支链取代基，则使用频哪醇硼烷作为[Cp * RuCl] 4催化的试剂对内部炔烃进行氢硼化可产生良好至极佳的区域选择性和立体选择性。在这种情况下，反应遵循不寻常的反加模式，并使硼实体远离分支点。否则难以制得的所得烯基硼酸酯可用于许多可行的下游工艺中。
• Rapid Assembly of Structurally Defined and Highly Functionalized Conjugated Dienes via Tethered Enyne Metathesis
  作者：Qingwei Yao

  DOI：10.1021/ol016026s

  日期：2001.6.1

  [reaction: see text] Conjugated dienes are versatile building blocks in organic synthesis, and the development of new methods for their synthesis remains an important topic in modern synthetic organic chemistry. We describe here an expedient synthesis of highly functionalized conjugated dienes through sequential silicon-tethered ring-closing enyne metathesis mediated by Grubbs' Ru carbene catalysts

  [反应：见正文]共轭二烯是有机合成中的通用构建基块，开发新的合成方法仍然是现代合成有机化学中的重要课题。我们在这里描述了通过功能性的合成方法，通过由Grubbs的Ru卡宾催化剂和Tamao氧化介导的连续硅束缚的闭环烯炔复分解来合成高度官能化的共轭二烯。该方法的显着属性包括合成操作时间短以及赋予所得二烯部分的结构复杂性。
• Luo, Tuoping; Schreiber, Stuart L., Journal of the American Chemical Society, 2009, vol. 131, p. 5667 - 5674
  作者：Luo, Tuoping、Schreiber, Stuart L.

  DOI：——

  日期：——
• Direct Access to Allenylphosphine Oxides via a Metal Free Coupling of Propargylic Substrates with P(O)H Compounds
  作者：Chun-Hua Yang、Huihui Fan、Huimin Li、Shenyin Hou、Xiangkun Sun、Donghao Luo、Yinchao Zhang、Zhantao Yang、Junbiao Chang

  DOI：10.1021/acs.orglett.9b03645

  日期：2019.12.6

  A direct and convenient approach for the coupling of propargylic substrates with diphenylphosphine oxide in the presence of Tf2O and 2,6-lutidine has been developed. The method provides a general approach for the construction of attractive allenylphosphoryl skeletons with high atom and step economy under metal free conditions.
• Complex α-Pyrones Synthesized by a Gold-Catalyzed Coupling Reaction
  作者：Tuoping Luo、Stuart L. Schreiber

  DOI：10.1002/anie.200703276

  日期：2007.11.5

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