(Z)-2-methyl-2,4-pentadien-1-ol | 67065-88-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-2-methyl-2,4-pentadien-1-ol
• 英文别名: (Z)-2-methylpenta-2,4-dien-1-ol；(2Z)-2-methyl-2,4-pentadienol；(Z)-2-methyl-penta-2,4-dien-1-ol；(2Z)-2-methylpenta-2,4-dien-1-ol
• CAS: 67065-88-7
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: NZJRNQDNEIHNQL-XQRVVYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (Z)-2-methyl-2,4-pentadien-1-ol 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 Hoveyda-Grubbs catalyst second generation 、 cerium(III) chloride heptahydrate 、 4-甲基苯磺酸吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 43.5h， 生成 (E)-ethyl 3-((3aR,4R,5S)-2-(4-methoxybenzyl)-3a-methyl-5-((E)-4-methylpent-2-en-2-yl)-1-oxo-2,3,3a,4,5,6-hexahydro-1H-isoindol-4-yl)acrylate
  参考文献：
  名称：

  An Efficient Synthesis of the Fully Elaborated Isoindolinone Unit of Muironolide A

  摘要：

  An efficient stereocontrolled construction of the fully substituted isoindolone subunit of muironolide A is described. The approach is centered on the intramolecular Diels-Alder reaction between the enol form of the beta-keto amide and an alpha,beta,gamma,delta-unsaturated ester, followed by the installation of the cyclohexene double bond.

  DOI：

  10.1021/ol401354a
• 作为产物：
  描述：

  2-[二(2,2,2-三氟乙氧基)磷酰]丙酸乙酯 、 丙烯醛 在 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.25h， 以70%的产率得到(Z)-2-methyl-2,4-pentadien-1-ol
  参考文献：
  名称：

  Construction of the A ring of halichomycin via a RCM strategy

  摘要：

  Attempts to the synthesis of the A ring of halichomycin via ring-closing metathesis (RCM) reaction were investigated. When triene 5 was used as the precursor of cyclization, only unexpected byproduct aldehyde 17 was obtained. When diene 6 was used as the precursor of cyclization, the desired product 20 was obtained in reasonable yield. This work demonstrated that both modification of the substrate and the RCM reaction conditions are important for obtaining the desired 11-membered macrocycle in reasonable yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.027

文献信息

• Stereocontrolled Synthesis of <i>Z</i>-Dienes via an Unexpected Pericyclic Cascade Rearrangement of 5-Amino-2,4-pentadienals
  作者：Sarah E. Steinhardt、Joel S. Silverston、Christopher D. Vanderwal

  DOI：10.1021/ja8028125

  日期：2008.6.18

  Donor-acceptor dienes known as Zincke aldehydes, which derive readily from the ring-opening reactions of pyridinium salts with secondary amines, undergo a fascinating thermal rearrangement reaction to afford Z-alpha,beta,gamma,delta-unsaturated amides with excellent stereoselectivity. Efficient, stereocontrolled access to Z-trisubstituted alkenes with two different substitution patterns is possible

  被称为锌醛的供体 - 受体二烯很容易从吡啶盐与仲胺的开环反应中衍生出来，经过引人入胜的热重排反应以提供具有优异立体选择性的 Z-α、β、γ、δ-不饱和酰胺。从适当取代的吡啶衍生物开始，可以通过三个步骤有效地、立体控制地获得具有两种不同取代模式的 Z-三取代烯烃。初步研究表明，酰胺和单取代的烯烃末端都可以选择性地官能化。易于获取、范围的普遍性和容易的产品操作使该过程对复杂多烯的合成具有吸引力。
• Stereoselective Synthesis of Pyrans from Epoxyalkenes: Dual Catalysis with Palladium and Brønsted Acid
  作者：Noah A. Setterholm、Frank E. McDonald

  DOI：10.1021/acs.joc.8b00026

  日期：2018.6.15

  We describe regio- and stereoselective cycloisomerizations of alcohols tethered to epoxyalkenes, to construct alkene-substituted pyrans. These transformations are best catalyzed by Pd(PPh3)4 in the presence of phosphite ligands, and with diphenylphosphinic acid as an essential Brønsted acid cocatalyst for activation of the epoxyalkene.

  我们描述了拴在环氧烯烃上的醇的区域和立体选择性环异构化，以构建烯烃取代的吡喃。这些转化最好在亚磷酸酯配体存在的情况下，由Pd（PPh 3）4催化，并以二苯基次膦酸为必要的布朗斯台德酸助催化剂来活化环氧烯烃。
• Cu-Catalyzed Divergent Transformations of Allenylethylene Carbonates with Diboron Reagents
  作者：Sijie Chen、Xiaojie Su、Yujie Dong、Jun Liu、Fazhou Yang、Hongchao Guo、Cheng Zhang

  DOI：10.1021/acs.orglett.3c04316

  日期：2024.2.2

  4-dioxane as the solvent. And they react with B2pin2 to form boronic half acids in the presence of NaOtBu as the base, water as the additive, and THF as the solvent. The reactions afford corresponding products in good stereoselectivities and yields, and further derivatizations of boronic half acids and study of the mechanism are also demonstrated.

  公开了由铜催化的丙二烯基碳酸亚乙酯与二硼试剂的发散转化。以CuCl/IPr·HCl为催化剂，在Cs 2 CO 3为碱、 i PrOH为溶剂的条件下，烯基碳酸亚乙酯与B 2 hex 2反应生成2,4-二烯-1-醇。添加剂和1,4-二恶烷作为溶剂。在NaO t Bu为碱、水为添加剂、THF为溶剂的情况下，它们与B 2 pin 2反应生成硼半酸。该反应以良好的立体选择性和产率提供了相应的产物，并且还证明了硼半酸的进一步衍生化和机理研究。
• Construction of the A ring of halichomycin via a RCM strategy
  作者：Shiyong Mao、Yanxing Jia

  DOI：10.1016/j.tetlet.2013.06.027

  日期：2013.8

  Attempts to the synthesis of the A ring of halichomycin via ring-closing metathesis (RCM) reaction were investigated. When triene 5 was used as the precursor of cyclization, only unexpected byproduct aldehyde 17 was obtained. When diene 6 was used as the precursor of cyclization, the desired product 20 was obtained in reasonable yield. This work demonstrated that both modification of the substrate and the RCM reaction conditions are important for obtaining the desired 11-membered macrocycle in reasonable yield. (C) 2013 Elsevier Ltd. All rights reserved.
• An Efficient Synthesis of the Fully Elaborated Isoindolinone Unit of Muironolide A
  作者：Qing Xiao、Kyle Young、Armen Zakarian

  DOI：10.1021/ol401354a

  日期：2013.7.5

  An efficient stereocontrolled construction of the fully substituted isoindolone subunit of muironolide A is described. The approach is centered on the intramolecular Diels-Alder reaction between the enol form of the beta-keto amide and an alpha,beta,gamma,delta-unsaturated ester, followed by the installation of the cyclohexene double bond.