(3E,5E,7E,9E)-10-phenyl-deca-3,5,7,9-tetraen-2-one | 62695-68-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3E,5E,7E,9E)-10-phenyl-deca-3,5,7,9-tetraen-2-one
• 英文别名: (3E,5E,7E,9E)-10-phenyldeca-3,5,7,9-tetraen-2-one；navenone B
• CAS: 62695-68-5
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: ZEWIVXFRPUFJSZ-TZMGHXHMSA-N

物化性质

• 沸点：
  401.2±24.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E,E,E,E)-9-Phenyl-2,4,6,8-nonatetraenal 在 manganese(IV) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3E,5E,7E,9E)-10-phenyl-deca-3,5,7,9-tetraen-2-one
  参考文献：
  名称：

  Four- and Eight-Carbon Homologation of Benzaldehyde by (1Z,3Z)-Butyltelluro-1,3-Butadiene: Synthesis of Navenone B: Alarm Pheromone of the Mollusk Navanax inermis

  摘要：

  Four- and eight-carbon homologation of benzaldehydes is described. The hydrotelluration of (Z)-1-methoxy-but-1-en-3-ynes 1 afforded (1Z,3Z)-1-butyltelluro-4-methoxy-1,3-butadiene 2, this compound 2 underwent a Te/Li exchange reaction, and the butadienyllithium 3 obtained reacted with benzaldehyde to form the corresponding allylic alcohol 4 with total retention of configuration. The allylic alcohol 4a formed underwent acidic hydrolysis, resulting in 5-phenyl-(2E,4E)-dienal 5 (four-carbon homologation of benzaldehyde). Product 5 reacted with the butadienyllithium 3, affording the alcohol 9-phenyl-(1Z, 3Z,6E,8E)-1-methoxy-5-hydroxy-nonatetraene 6, which was hydrolyzed or spontaneously transformed into 9-phenyl-(2E, 4E, 6E, 8E)-tetraenal 7, completing the eight-carbon homologation of benzaldehyde. Reaction of 9-phenyl-nona-(2E,4E,6E,8E)-tetraenal 7 with methyllithium in tetrahydrofuran afforded (3E,5E,7E,9E)-10-phenyl-deca-3,5,7,9-tetraen-2-ol 8. The product of the reaction described was employed in the synthesis of (3E, 5E, 7E, 9E)-10-phenyl-deca-3,5,7,9-tetraen-2-one 9, which is known as navenone B, an alarm pheromone of the mollusk Navanax inermis.

  DOI：

  10.1080/00397911.2010.528131

文献信息

• Donor Rhodium Carbenes by Retro-Buchner Reaction
  作者：Mauro Mato、Antonio M. Echavarren

  DOI：10.1002/anie.201813512

  日期：2019.2.11

  of cycloadditions and insertion reactions. Herein, we report the first generation of donor RhII carbenes by decarbenation of 7‐substituted 1,3,5‐cycloheptatrienes. This discovery unlocks an improved retro‐Buchner‐cyclopropanation sequence, a Si−H insertion reaction for a broad‐scope synthesis of allylsilanes, and a new method for the vinylogation of aldehydes. The last strategy led to the development

  卡宾铑是一系列环加成反应和插入反应的关键中间体。在此，我们报告了通过7-取代的1,3,5-环庚庚烯的脱碳而生成的第一代供体Rh II卡宾。这一发现开启了改良的布氏环丙烷化反应的逆序，用于广谱合成烯丙基硅烷的Si-H插入反应以及醛类乙烯基化的新方法。最后一种策略导致了E-多烯的迭代合成的发展，以及navenones B和C的总合成。
• 1,<i>n</i>-Rearrangement of Allylic Alcohols Promoted by Hot Water: Application to the Synthesis of Navenone B, a Polyene Natural Product
  作者：Pei-Fang Li、Heng-Lu Wang、Jin Qu

  DOI：10.1021/jo5004086

  日期：2014.5.2

  n-rearrangement (n = 3, 5, 7, 9) of allylic alcohols. In some cases, the rearrangement reactions joined isolated C–C double or triple bonds to generate conjugated polyene or enyne structure motifs. We used the 1,3-rearrangement reaction of an allylic alcohol in hot water as part of an attractive new strategy for construction of the polyene natural product navenone B by iterative use of a Grignard reaction

  首次报道，作为弱酸性催化剂的热水有效地促进了烯丙醇的1，n重排（n = 3、5、7、9 ）。在某些情况下，重排反应会连接孤立的C双键或C键，从而生成共轭多烯或烯结构的基序。我们使用了烯丙醇在热水中的1,3-重排反应作为通过反复使用格利雅（Grignard）反应构建多烯天然产物navenone B的有吸引力的新策略的一部分，将所得烯丙基的1,3-重排酒精和随后氧化的重排产物。
• Stereoselective approaches to (E,E,E) and (Z,E,E)-α-chloro-ω-substituted hexatrienes: Synthesis of all E polyenes
  作者：Benoit Crousse、Margarita Mladenova、Pascal Ducept、Mouâd Alami、Gérard Linstrumelle

  DOI：10.1016/s0040-4020(99)00123-4

  日期：1999.4

  palladium-catalyzed rearrangement of bis-allylic acetates 4 and 5 and the second one is based on the stereoselective reduction of homopropargylic alcohols 6 followed by an elimination reaction. These stable chlorotrienes 1–3 are suitable synthetic intermediates for the construction of navenone B and allE polyenes (trienes, tetraenes, hexaenes and heptaenes).

  从不饱和化合物4-6开始，描述了两种立体控制合成方法（E，E，E）和（Z，E，E）-α-氯-ω-取代的己三烯1-3。第一种方法的关键步骤是基于钯催化的双烯丙基乙酸酯4和5的重排，第二种方法是基于立体选择性还原均炔醇6并随后进行消除反应。这些稳定的三氯乙烯1–3是用于构建navenone B和所有E多烯（三烯，四烯，己烯和庚烯）的合适的合成中间体。
• Simple Synthesis of Conjugated All-(<i>E</i>)-Polyenic Aldehydes, Ketones, and Esters Using Chemoselective Cross-Metathesis and an Iterative Sequence of Reactions: Application to the Synthesis of Navenone B
  作者：Samir BouzBouz、Janine Cossy、Christophe Roche

  DOI：10.1055/s-0028-1087953

  日期：——

  By using a very simple sequence of reactions such as allylation, acetylation, chemoselective cross-metathesis, and elimination, even and odd conjugated all-(E)-polyenes can be synthesized from very simple alkenes.

  通过使用非常简单的反应序列，例如烯丙基化、乙酰化、化学选择性交叉复分解和消除，可以从非常简单的烯烃合成偶数和奇数共轭全（E）-多烯。
• Sn/Li Exchange Reactions in 1,ω-Distannylated Conjugated Trienes and Tetraenes: An Enabling Step for Polyene Synthesis
  作者：Jochen Burghart、Reinhard Brückner

  DOI：10.1002/ejoc.201001231

  日期：2011.1

  polyenyl alcohols resulting from one Sn/Li exchange reaction and exhibiting complete retention of the configuration of all C=C bonds. Mono- or dimethylated all-E-configured 1,6-distannylated conjugated trienes as well as all-E-1,8-bis(tributylstannyl)octa-1,3,5,7-tetraene and dimethylated congeners thereof reacted similarly. The respective Sn/Li exchange reactions affected the substructure Bu 3 Sn-CH=CH

  (1E,3E,5E)- 或 (1E,3Z,5E)-1,6-bis(tri-butylstannyl)hexa-1,3,5-triene 用 nBuLi 和丁醛连续处理由一种 Sn 产生的多烯醇/Li 交换反应并完全保留所有 C=C 键的构型。单-或二甲基化全-E-构型的1,6-二甲锡烷基化共轭三烯以及全-E-1,8-双(三丁基甲锡烷基)octa-1,3,5,7-四烯及其二甲基化同系物反应类似。相应的 Sn/Li 交换反应影响了亚结构 Bu 3 Sn-CH=CH，比 Bu 3 Sn-CMe=CH 的优先级为 93-94:7-6，比 Bu 3 Sn-CH=CMe 的优先级为 90:10 . All-E-1-Lithio-6-(tributylstannyl)hexa-1,3,5-triene 在 Negishi 偶联后掺入 navenone B 中，酰化后掺入 (-)-cicutoxin。