nona-2ξ,6c-dienal | 1048031-88-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: nona-2ξ,6c-dienal
• 英文别名: (6Z)-nona-2,6-dienal
• CAS: 1048031-88-4
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: HZYHMHHBBBSGHB-OQTZDUBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  nona-2ξ,6c-dienal 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 sodium acetate 、 silica gel 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 22.17h， 生成 (R,Z)-methyl 2-(dimethylamino)-5-(1-(4-methylphenylsulfonamido)hept-4-enyl)thiophene-3-carboxylate
  参考文献：
  名称：

  Optically Active Thiophenes via an Organocatalytic One-Pot Methodology

  摘要：

  A general methodology for the synthesis of trisubstituted, optically active thiophenes by an organocatalytic one-pot reaction cascade is presented. The target products are synthesized in good yields (up to 92%) and with excellent enantioselectivities (up to 98% ee). Importantly, based on practical and easily available starting materials, the presented methodology can be conducted under mild reaction conditions. To further elucidate the generality, the synthesis of optically active thienoindoles, as well as selenophenes, is also demonstrated.

  DOI：

  10.1021/ol203237r

文献信息

• cis-4-Alkoxydialkyl- andcis-4-Alkoxydiarylprolinol Organocatalysts: High Throughput Experimentation (HTE)-Based and Design of Experiments (DoE)-Guided Development of a Highly Enantioselectiveaza-Michael Addition of Cyclic Imides to α,β-Unsaturated Aldehyd
  作者：Ismael Arenas、Alessandro Ferrali、Carles Rodríguez-Escrich、Fernando Bravo、Miquel A. Pericàs

  DOI：10.1002/adsc.201700120

  日期：2017.7.17

  catalysts for the enantioselective addition of succinimide to α,β‐unsaturated aldehydes. Further optimization of the reaction conditions with design of experiments (DoE) techniques established the catalyst of choice for the considered aza‐Michael reaction, the corresponding adducts (12 examples) being obtained in good yields and excellent enantioselectivities (succinimide and maleimide donors). The synthetic

  制备了多种顺式-4-烷氧基二有机基脯氨醇衍生物家族（37种化合物），并首次在有机催化中进行了评估。高通量实验（HTE）技术与有效的分析方法的结合使用，导致鉴定出两种优良的催化剂，可将琥珀酰亚胺对映选择性地加成到α，β-不饱和醛中。通过实验设计（DoE）技术进一步优化反应条件，为所考虑的氮杂选择催化剂奠定了基础‐Michael反应，以高收率和优异的对映选择性（琥珀酰亚胺和马来酰亚胺供体）获得相应的加合物（12个实例）。这些迈克尔加合物的合成多功能性通过两步序列得到说明，该对数序列导致对映体纯的1,3-氨基醇。
• Enantioselective Synthesis of Polysubstituted Cyclopentanones by Organocatalytic Double Michael Addition Reactions
  作者：Anqi Ma、Dawei Ma

  DOI：10.1021/ol101414b

  日期：2010.8.20

  diphenylprolinol-catalyzed cascade double Michael addition reactions of α,β-unsaturated aldehydes with a β-keto ester bearing a highly electron-deficient olefin unit occur smoothly to afford polysubstituted cyclopentanones. This process allows formation of four contiguous stereocenters in the cyclopentanone ring in one-step with excellent enantioselectivity.

  α，β-不饱和醛与带有高度缺电子的烯烃单元的β-酮酯的O -TMS保护的二苯基脯氨醇催化的级联双迈克尔加成反应顺利进行，得到多取代的环戊酮。该方法允许一步法以优异的对映选择性在环戊酮环中形成四个连续的立体中心。
• Organocatalytic asymmetric epoxidation and tandem epoxidation/Passerini reaction under eco-friendly reaction conditions
  作者：Anna Maria Deobald、Arlene G. Corrêa、Daniel G. Rivera、Márcio Weber Paixão

  DOI：10.1039/c2ob26247a

  日期：——

  An eco-friendly synthesis of highly functionalized epoxides and their incorporation into an organocatalytic multicomponent approach are reported. For this, a modified class of diarylprolinol silyl ethers was designed to enable high catalytic activity in an environmentally benign solvent system. The one-pot procedure showed great efficiency in promoting stereoselective multicomponent transformations in a tandem, ‘green’ fashion. Because of its non-residual, efficient and selective character, this synthetic design shows promise for large-scale applications in both diversity and target-oriented syntheses.

  报道了一种环保的高功能化环氧化物合成方法，并将其应用于有机催化多组分反应策略。为此，设计了一类改良的二芳基脯氨醇硅醚，以在环境友好的溶剂体系中实现高催化活性。该一步法程序非常有效，能够促进立体选择性多组分反应以连贯、环保的方式进行。由于其无残留、高效和选择性的特点，这种合成设计在多样的和目标导向的合成中具有大规模应用的潜力。
• Enantioselective Conjugate Addition of Donor–Acceptor Hydrazones to α,β-Unsaturated Aldehydes through Formal Diaza–Ene Reaction: Access to 1,4-Dicarbonyl Compounds
  作者：Maitane Fernández、Uxue Uria、Jose L. Vicario、Efraím Reyes、Luisa Carrillo

  DOI：10.1021/ja3041042

  日期：2012.7.25

  Donor-acceptor monosubstituted hydrazones participate as suitable reagents able to undergo an enantioselective formal diaza-ene reaction with α,β-unsaturated aldehydes under chiral secondary amine catalysis. This constitutes a new approach for the enantioselective conjugate addition of hydrazones to enals under metal-free conditions and leads to the formation of γ-hydrazono carboxylic acids after oxidation/[1

  供体-受体单取代腙作为合适的试剂参与，能够在手性仲胺催化下与α,β-不饱和醛进行对映选择性的二氮杂烯反应。这构成了在无金属条件下腙与烯醛的对映选择性共轭加成的新方法，并导致在氧化/[1,3]-H 转移后形成 γ-腙羧酸。该方法还可用于通过使用腙部分作为掩蔽羰基来合成富含对映体的 β-取代的 α-酮-1,5-二酯。
• Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights
  作者：Ane Orue、Uxue Uria、David Roca-López、Ignacio Delso、Efraím Reyes、Luisa Carrillo、Pedro Merino、Jose L. Vicario

  DOI：10.1039/c7sc00009j

  日期：——

  polyfunctional reagents able to react with enals through oxa-Michael/Michael process cascade under the combination of iminium and enamine catalysis. These racemic hemiacetalic compounds are used as unconventional O-pronucleophiles in the initial oxa-Michael reaction, also leading to the formation of a single stereoisomer under a dynamic kinetic resolution (DKR) process. Importantly, by using β-aryl or β-alkyl

  2-羟基二氢吡喃-5-酮是一种优异的多官能试剂，能够在亚胺和烯胺催化下通过 oxa-Michael/Michael 级联反应与烯醛发生反应。这些外消旋半缩醛化合物在最初的 oxa-Michael 反应中用作非常规的O -亲核试剂，也导致在动态动力学拆分 (DKR) 过程中形成单一立体异构体。重要的是，通过使用β-芳基或β-烷基取代的α,β-不饱和底物作为初始迈克尔受体，通过仔细选择反应条件，形成动力学或热力学控制的非对映异构体，并具有高度立体选择。最后，完整的实验和计算研究证实了最初提出的催化 oxa-Michael/Michael 级联反应过程中的 DKR 过程，并解释了每种情况下运行的动力学/热力学途径。