5,9-dimethyl-1,4,8-decatrien-3-ol | 5208-88-8

• 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: 5,9-dimethyl-1,4,8-decatrien-3-ol
• 英文别名: 5,9-dimethyldeca-1,4,8-trien-3-ol；5,9-Dimethyl-1,4,8-decatrien-3-ol
• CAS: 5208-88-8
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: SQYSUSPBXAWDAK-UHFFFAOYSA-N

物化性质

• 沸点：
  118-122 °C(Press: 6 Torr)
• 密度：
  0.8952 g/cm3(Temp: 21 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  5,9-dimethyl-1,4,8-decatrien-3-ol 在 2C₂₅H₂₈N₂OP^(1-)*2Cl^(1-)*2Ru⁽²⁺⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以91%的产率得到5,9-dimethyl-1,4,8-decatrien-3-ol
  参考文献：
  名称：

  Tethered η⁵-Oxocyclohexadienyl Piano-Stool Ruthenium(II) Complexes: A New Class of Catalysts?

  摘要：

  The straightforward synthesis of tethered eta(5)-oxocyclohexadienyl Ru(II) complexes is presented. Pioneering results in catalysis show that these original half-sandwich Ru(II) complexes allow the effective isomerization of allylic alcohols under mild conditions without further additives; eta(5)-oxocyclohexadienyl ruthenium complexes may be considered as a new class of catalysts.

  DOI：

  10.1021/om501073q
• 作为产物：
  描述：

  乙烯基溴化镁 、 柠檬醛 以 四氢呋喃 为溶剂， 以65%的产率得到5,9-dimethyl-1,4,8-decatrien-3-ol
  参考文献：
  名称：

  烯丙基醇的铱催化异构化/溴化反应：α-溴羰基化合物的合成

  摘要：

  具有两个相邻亲电子碳原子的α-溴化酮和醛是有机合成中非常有价值的合成中间体，但是，它们由不对称酮合成的过程非常具有挑战性，当前的方法具有选择性低的缺点。我们提供了一种新的，可靠的，高效的合成α-溴羰基化合物的方法，该方法具有优异的收率和优异的选择性。从烯丙基醇作为羰基前体开始，铱（III）催化的1,3-氢转移与亲电溴化反应可很好地产生高纯度的α-溴代酮和醛。该方法的选择性由起始烯丙基醇的结构决定。因此，

  DOI：

  10.1002/chem.201402350

文献信息

• Cp*Co(III)‐Catalyzed Dehydrative C2‐Prenylation of Pyrrole and Indole with Allyl Alcohols
  作者：Suchand Basuli、Samrat Sahu、Shuvendu Saha、Modhu Sudan Maji

  DOI：10.1002/adsc.202100811

  日期：2021.10.5

  Non-activated allyl alcohols are utilized as allylating agent for thiocarbamate-directed allylation of pyrrole and indole. The synthetic methodology is accompanied by advantages like silver-free conditions and generates water as the by-product. A wide range of substituted pyrroles and indoles along with several structurally different allyl alcohols took part in the reaction. Among notable examples

  未活化的烯丙醇用作吡咯和吲哚的硫代氨基甲酸酯导向的烯丙基化的烯丙基化剂。合成方法伴随着无银条件等优点，并产生水作为副产品。多种取代的吡咯和吲哚以及几种结构不同的烯丙醇参与了反应。在值得注意的例子中，实现了 1,3-二烯的生物学相关异戊二烯化、香叶基化和合成。吡咯的选择性单烯丙基化、克级合成和导向基团的脱保护是该方法的另一个关键亮点。
• 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.
• A general method for the synthesis of amines by the rearrangement of allylic trichloroacetimidates. 1,3 Transposition of alcohol and amine functions
  作者：Larry E. Overman

  DOI：10.1021/ja00426a038

  日期：1976.5
• Iridium-Catalyzed Isomerization/Bromination of Allylic Alcohols: Synthesis of α-Bromocarbonyl Compounds
  作者：Antonio Bermejo Gómez、Elis Erbing、María Batuecas、Ana Vázquez-Romero、Belén Martín-Matute

  DOI：10.1002/chem.201402350

  日期：2014.8.18

  yields and with excellent selectivities. Starting from allylic alcohols as the carbonyl precursors, the combination of a 1,3‐hydrogen shift catalyzed by iridium(III) with an electrophilic bromination gives α‐bromoketones and aldehydes in good to excellent yields. The selectivity of the process is determined by the structure of the starting allylic alcohol; thus, α‐bromoketones formally derived from unsymmetrical

  具有两个相邻亲电子碳原子的α-溴化酮和醛是有机合成中非常有价值的合成中间体，但是，它们由不对称酮合成的过程非常具有挑战性，当前的方法具有选择性低的缺点。我们提供了一种新的，可靠的，高效的合成α-溴羰基化合物的方法，该方法具有优异的收率和优异的选择性。从烯丙基醇作为羰基前体开始，铱（III）催化的1,3-氢转移与亲电溴化反应可很好地产生高纯度的α-溴代酮和醛。该方法的选择性由起始烯丙基醇的结构决定。因此，
• Tethered η⁵-Oxocyclohexadienyl Piano-Stool Ruthenium(II) Complexes: A New Class of Catalysts?
  作者：Manel Kechaou-Perrot、Laure Vendier、Stéphanie Bastin、Jean-Marc Sotiropoulos、Karinne Miqueu、Lucía Menéndez-Rodríguez、Pascale Crochet、Victorio Cadierno、Alain Igau

  DOI：10.1021/om501073q

  日期：2014.11.24

  The straightforward synthesis of tethered eta(5)-oxocyclohexadienyl Ru(II) complexes is presented. Pioneering results in catalysis show that these original half-sandwich Ru(II) complexes allow the effective isomerization of allylic alcohols under mild conditions without further additives; eta(5)-oxocyclohexadienyl ruthenium complexes may be considered as a new class of catalysts.