(3E,5E,7E,9E)-10-phenyl-deca-3,5,7,9-tetraen-2-ol | 172515-96-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3E,5E,7E,9E)-10-phenyl-deca-3,5,7,9-tetraen-2-ol
• 英文别名: (3E,5E,7E,9E)-10-phenyldeca-3,5,7,9-tetraen-2-ol
• CAS: 172515-96-7
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: XGWHROXXUMXTCL-TZMGHXHMSA-N

物化性质

• 沸点：
  391.9±11.0 °C(Predicted)
• 密度：
  1.007±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：
  0.12
• 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：

  (3E,5E,7E,9E)-10-phenyl-deca-3,5,7,9-tetraen-2-ol 在 manganese(IV) oxide 作用下， 以 四氢呋喃 为溶剂， 以83 %的产率得到(3E,5E,7E,9E)-10-phenyl-deca-3,5,7,9-tetraen-2-one
  参考文献：
  名称：

  铱催化的烯丙醇 1,3-重排

  摘要：

  实现了有效的 Ir(III) 二氢化物络合物催化烯丙醇的 1,3-重排，从容易获得的起始材料中以高收率区域选择性和立体选择性地提供相应的不易获得的烯丙醇。反应途径涉及 π-烯丙基-Ir(V) 中间体，Ir(III) 二氢化物络合物中的二氢化物作为氢开关调节铱中心的化合价。

  DOI：

  10.1002/chem.202300027
• 作为产物：
  描述：

  (2E, 4E)-5-phenylpenta-2,4-dienal 在 正丁基锂 、 硫酸 、 silica gel 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.52h， 生成 (3E,5E,7E,9E)-10-phenyl-deca-3,5,7,9-tetraen-2-ol
  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

• 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。
• Stereocontrolled synthesis of (E,E,E)-chlorotrienes: Efficient intermediates for the construction of all E conjugated polyenes
  作者：Benoit Crousse、Mouâd Alami、Gérard Linstrumelle

  DOI：10.1016/s0040-4039(97)01156-8

  日期：1997.7

  Stereoselective reduction of conjugated homopropargylic alcohols 1 followed by an elimination reaction, allows an efficient approach to stereodefined (E,E,E)-chlorotrienes. The interest of these chlorotrienes was illustrated by a stereocontrolled synthesis of navenone B and allE conjugated polyenes (trienes, tetraenes and hexaenes).

  立体选择性还原共轭均炔丙醇1，然后进行消除反应，可以实现立体定义的（E，E，E）-氯三烯的有效方法。这些碳三烯的兴趣通过navenone B和所有E共轭多烯（三烯，四烯和己烯）的立体控制合成得到了说明。
• Stereoselective synthesis of polyenic alarm pheromones of cephalaspidean molluscs
  作者：Rosana Alvarez、María Herrero、Susana López、Angel R. de Lera

  DOI：10.1016/s0040-4020(98)00363-9

  日期：1998.6

  The stereospecific thallium-accelerated palladium-catalyzed cross-coupling of I-alkenyl boronic acids and I-alkenyl iodides (the Suzuki reaction) is the key step in an efficient approach to several polyenic pheromones isolated from cephalaspidean opisthobranch molluscs. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Four- and Eight-Carbon Homologation of Benzaldehyde by (1<i>Z</i>,3<i>Z</i>)-Butyltelluro-1,3-Butadiene: Synthesis of Navenone B: Alarm Pheromone of the Mollusk <i>Navanax inermis</i>
  作者：Miguel J. Dabdoub、Vânia B. Dabdoub、Adriano C. M. Baroni、Sandro L. Barbosa

  DOI：10.1080/00397911.2010.528131

  日期：2012.4.1

  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.