(5R)-5,9-dimethyl-1,8-decadien-3-ol | 1037496-91-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5R)-5,9-dimethyl-1,8-decadien-3-ol
• 英文别名: 5,9-dimethyl-1,8-decadien-3-ol；(5R)-5,9-dimethyldeca-1,8-dien-3-ol
• CAS: 1037496-91-5
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: BNOYHAFSQXFIJN-JHJMLUEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (5R)-5,9-dimethyl-1,8-decadien-3-ol 在 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 、 二乙醇胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 26.0h， 生成 (7R)-2,7,11-trimethyl-5-oxododec-10-enal
  参考文献：
  名称：

  Total synthesis of bisabolane sesquiterpenoids, α-bisabol-1-one, curcumene, curcuphenol and elvirol: utility of catalytic enamine reaction in cyclohexenone synthesis

  摘要：

  已经通过将完整的醛与烯烃酮进行1,4互补加成，随后进行分子内醛醇缩合，实现了α-大马士革烯-1-酮、姜烯、姜苯醇和艾维醇的全合成。

  DOI：

  10.1039/b200629b
• 作为产物：
  描述：

  溴乙烯 、 (+)-香茅醛 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以100%的产率得到(5R)-5,9-dimethyl-1,8-decadien-3-ol
  参考文献：
  名称：

  Total synthesis of bisabolane sesquiterpenoids, α-bisabol-1-one, curcumene, curcuphenol and elvirol: utility of catalytic enamine reaction in cyclohexenone synthesis

  摘要：

  已经通过将完整的醛与烯烃酮进行1,4互补加成，随后进行分子内醛醇缩合，实现了α-大马士革烯-1-酮、姜烯、姜苯醇和艾维醇的全合成。

  DOI：

  10.1039/b200629b

文献信息

• Synthetic Scope of Ru(OH)x/Al2O3-Catalyzed Hydrogen-Transfer Reactions: An Application to Reduction of Allylic Alcohols by a Sequential Process of Isomerization/Meerwein-Ponndorf-Verley-Type Reduction
  作者：Jung Won Kim、Takeshi Koike、Miyuki Kotani、Kazuya Yamaguchi、Noritaka Mizuno

  DOI：10.1002/chem.200701917

  日期：2008.4.28

  Reduction of allylic alcohols can be promoted efficiently by the supported ruthenium catalyst Ru(OH)x/Al2O3. Various allylic alcohols were converted to saturated alcohols in excellent yields by using 2-propanol without any additives. This Ru(OH)x/Al2O3-catalyzed reduction of a dienol proceeds only at the allylic double bond to afford the corresponding enol, and chemoselective isomerization and reduction

  负载型钌催化剂Ru（OH）x / Al2O3可以有效地促进烯丙基醇的还原。通过使用不含任何添加剂的2-丙醇，各种烯丙基醇以优异的产率转化为饱和醇。Ru（OH）x / Al2O3催化的二烯醇的还原仅在烯丙基双键处进行以提供相应的烯醇，并且可以在相似的条件下实现化学选择性异构化和还原。催化确实是非均相的，并且可以在Ru（OH）x / Al2O3催化剂的至少三个循环中保持高催化性能。烯丙醇向饱和醇的转化包括三个顺序的反应：烯丙醇氧化为α，β-不饱和羰基化合物; 降低阿尔法，β-不饱和羰基化合物为饱和羰基化合物；并将饱和羰基化合物还原为饱和醇。
• <i>p</i>-Cresol-Enabled Nickel-Catalyzed Intermolecular Redox-Economical Coupling of Allyl Alcohols with Alkynes through oxa-Nickelacycle
  作者：Rong-Hua Wang、Zhou Zhang、Bo Li、Gao-Feng Zhu、Jing Shi、Lei Tang

  DOI：10.1021/acs.orglett.3c03320

  日期：2023.12.1

  An intermolecular redox-economical coupling reaction of allyl alcohols with alkynes, catalyzed by Ni-Brønsted acid cocatalysis, has been developed. This method allows for the synthesis of a diverse range of γ,δ-unsaturated ketones with yields ranging from 40% to 94%, while maintaining excellent compatibility with various functional groups. The transformation of the resulting product demonstrates the

  在镍布朗斯台德酸助催化下，烯丙醇与炔烃的分子间氧化还原经济偶联反应已被开发出来。该方法可以合成多种 γ,δ-不饱和酮，产率范围为 40% 至 94%，同时保持与各种官能团的优异相容性。所得产品的转化证明了该方法的重要实用价值。进一步的机理研究表明，该反应是通过形成氧杂镍环中间体进行的。
• Catalytic isomerization of allylic alcohols promoted by complexes [RuCl2(η6-arene)(PTA-Me)] under homogeneous conditions and supported on Montmorillonite K-10
  作者：Lucía Menéndez-Rodríguez、Pascale Crochet、Victorio Cadierno

  DOI：10.1016/j.molcata.2012.10.025

  日期：2013.1

  The mononuclear arene-ruthenium(II) derivatives [RuCl2(eta(6)-arene)(PTA-Me)] (arene = C6H6 (3a), p-cymene (3b), 1,3,5-C6H3Me3 (3c), C6Me6 (3d)), containing the ionic phosphine ligand 1-methyl-3,5-diaza-1-azonia-7-phosphaadamantane chloride (PTA-Me), have been synthesized and fully characterized. These complexes were evaluated as potential catalysts for the redox isomerization of allylic alcohols. Among them, best results in terms of activity were obtained with complex [RuCl2(eta(6)-C6H6)(PTA-Me)] (3a) which, in combination with K2CO3 (2.5 equiv. per Ru), was able to selectively isomerize a number of allylic alcohols RCH(OH)CH=CH2 (R = H, aryl, alkyl or heteroaryl group) into the corresponding carbonyl compounds RC(=O)CH2CH3 in refluxing THF (TOF values up to 800 h(-1)). Complex [RuCl2(eta(6)-C6H6)(PTA-Me)] (3a) was adsorbed onto the Montmorillonite K-10 clay, and the resulting solid proved also active in the isomerization of the model substrate 1-octen-3-ol. In addition, it could be easily separated from the reaction media by simple filtration and reused several times (up to 11 consecutive runs) with retention of its efficiency. (c) 2012 Elsevier B.V. All rights reserved.