(2E,4E)-3-methyl-5-phenyl-2,4-pentadien-1-ol | 71687-03-1

• 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: (2E,4E)-3-methyl-5-phenyl-2,4-pentadien-1-ol
• 英文别名: (2E,4E)-3-methyl-5-phenylpenta-2,4-dien-1-ol；(2E,4E)-3-methyl-5-phenylpenta-2,4-dienol；5-Phenyl-3-methyl-penta-2,4-dien-1-ol
• CAS: 71687-03-1
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: BKMOTRYJJUELQA-MFDVASPDSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  296.3±9.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	ethyl (2E,4E)-3-methyl-5-phenylpenta-2,4-dienoate	41436-08-2	C14H16O2	216.28
  苄叉丙酮	1-Phenylbut-1-en-3-one	122-57-6	C10H10O	146.189

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(2E,4E)-3-methyl-5-phenylpenta-2,4-dienal	53701-48-7	C12H12O	172.227

反应信息

• 作为反应物：
  描述：

  (2E,4E)-3-methyl-5-phenyl-2,4-pentadien-1-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以82%的产率得到(2E,4E)-3-methyl-5-phenylpenta-2,4-dienal
  参考文献：
  名称：

  跨复分解方法合成新的维甲酸类维生素A，维甲酸乙酯及其9 Z-异构体

  摘要：

  使用一种新方法，以交叉复分解反应为关键步骤，从苯乙烯衍生物合成了两种芳香族类维生素A。测试了新的维甲酸类似物的生物活性。跨复分解反应还用于通过C 15  + C 5途径制备视黄酸乙酯及其9 Z-异构体。

  DOI：

  10.1016/j.tetlet.2012.07.122
• 作为产物：
  描述：

  triethyl 3-methyl-4-phosphonocrotonate 在 N,N-二甲基丙烯基脲 、 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 1.66h， 生成 (2E,4E)-3-methyl-5-phenyl-2,4-pentadien-1-ol
  参考文献：
  名称：

  Photocurrents of solar cells sensitized by aggregate-forming polyenes: Enhancement due to suppression of singlet–triplet annihilation by lowering of dye concentration or light intensity

  摘要：

  Titania-based Gratzel-type solar cells were fabricated by the use of polyene dyes with various transition dipole moments. in the dye having the largest transition dipole among the samples, an aggregate was readily formed through dispersive interaction, and the photocurrent was increased when the dye concentration or the light intensity was lowered. This observation was ascribed to the suppression of the singlet-triplet annihilation reaction. In the dye having the smallest transition dipole, there was no sign of aggregate formation, and the photocurrent was decreased when the dye concentration or the light intensity was lowered. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cplett.2006.01.003

文献信息

• Peptide-Catalyzed Regio- and Enantioselective Reduction of α,β,γ,δ-Unsaturated Aldehydes
  作者：Kengo Akagawa、Jun Sen、Kazuaki Kudo

  DOI：10.1002/anie.201305004

  日期：2013.10.25

  in the title reaction. The inherent regioselectivity was overcome by the peptide catalyst to promote the 1,6‐selective reaction prior to 1,4‐reduction. High stereoconvergence was also achieved when using a mixture of geometric isomers of the starting aldehydes. Ach=1‐amino‐1‐cyclohexanecarboxylic acid.

  在标题反应中使用了树脂负载的肽催化剂（参见方案中的方框）。肽催化剂克服了固有的区域选择性，从而在1,4还原之前促进了1,6选择性反应。当使用起始醛的几何异构体的混合物时，也实现了高立体收敛性。Ach = 1-氨基-1-环己烷羧酸
• A One-Pot Synthesis of (E)-Disubstituted Alkenes by a Bimetallic [Rh–Pd]-Catalyzed Hydrosilylation/Hiyama Cross-Coupling Sequence
  作者：Carine Thiot、Marc Schmutz、Alain Wagner、Charles Mioskowski

  DOI：10.1002/chem.200700811

  日期：2007.11.5

  (E)-adduct. The [Rh-Pd] heterogeneous catalyst also showed a higher chemoselectivity than the homogeneous catalytic combination, and no detrimental formation of Sonogashira side product was observed due to an ionic-gel-mediated kinetic modulation. To illustrate its scope and limitations, the described one-pot bimetallic catalytic sequence was extended to functionalized terminal alkynes and various iodide

  通过将[RhCl（PPh（3））（3）]和Pd（OAc）（2）在CH（2）Cl（2）中的等摩尔溶液浸入碘离子凝胶中来制备双金属[Rh-Pd]催化剂。通过铑催化的氢化硅烷化（H），钯催化的Hiyama偶联（C）和一锅加氢硅烷化/ Hiyama偶联顺序（H / C）评估其催化活性。发现在末端炔烃的氢化硅烷化中，与聚离子单金属和双金属铑催化剂相比，[RhCl（PPh（3））（3）] / NaI均相组合是一种优越的体系。有趣的是，在立体反应和化学选择性方面，观察到最有效的催化剂是一锅法制备双（E）-烯烃的双金属离子凝胶[Rh-Pd]。显着的立体控制归因于从初始氢化硅烷化步骤中获得的立体异构体乙烯基硅烷混合物到更稳定的（E）加合物中的Pd催化异构化。[Rh-Pd]非均相催化剂还显示出比均相催化组合更高的化学选择性，并且由于离子凝胶介导的动力学调节，未观察到Sonogashira副产物的有害形成。为了
• Low Coordination State Rh ^I ‐Complex as High Performance Catalyst for Asymmetric Intramolecular Cyclopropanation: Construction of <i>penta</i> ‐Substituted Cyclopropanes
  作者：Junyou Zhang、Weici Xu、Ming‐Hua Xu

  DOI：10.1002/anie.202216799

  日期：2023.3

  broad-scope rhodium (I)/chiral diene catalytic system has been developed that allows otherwise difficult-to-access penta-substituted cyclopropanes to be prepared in a highly enantioselective manner through asymmetric intramolecular cyclopropanation of rather challenging tri-substituted allylic diazoacetates. Extraordinary high performance of RhI/diene complex is showcased with low catalyst loading as little

  已开发出一种简单、广泛的铑 (I)/手性二烯催化体系，该体系允许通过相当具有挑战性的三取代烯丙基重氮乙酸酯的不对称分子内环丙烷化，以高度对映体选择性的方式制备难以获得的五取代环丙烷. 在低至 0.1 mol% 的低催化剂负载下，展示了Rh I /二烯配合物的非凡高性能。
• Photocurrents of solar cells sensitized by aggregate-forming polyenes: Enhancement due to suppression of singlet–triplet annihilation by lowering of dye concentration or light intensity
  作者：Xiao-Feng Wang、Yasushi Koyama、Hiroyoshi Nagae、Yumiko Yamano、Masayoshi Ito、Yuji Wada

  DOI：10.1016/j.cplett.2006.01.003

  日期：2006.3

  Titania-based Gratzel-type solar cells were fabricated by the use of polyene dyes with various transition dipole moments. in the dye having the largest transition dipole among the samples, an aggregate was readily formed through dispersive interaction, and the photocurrent was increased when the dye concentration or the light intensity was lowered. This observation was ascribed to the suppression of the singlet-triplet annihilation reaction. In the dye having the smallest transition dipole, there was no sign of aggregate formation, and the photocurrent was decreased when the dye concentration or the light intensity was lowered. (c) 2006 Elsevier B.V. All rights reserved.
• A cross-metathesis approach to the synthesis of new etretinate type retinoids, ethyl retinoate and its 9Z-isomer
  作者：Jadwiga Maj、Jacek W. Morzycki、Lucie Rárová、Grzegorz Wasilewski、Agnieszka Wojtkielewicz

  DOI：10.1016/j.tetlet.2012.07.122

  日期：2012.10

  retinoids were synthesized from styrene derivatives using a novel strategy with a cross-metathesis reaction as a key step. The biological activity of the new etretinate analogues was tested. Cross-metathesis reactions were also employed for the preparation of ethyl retinoate and its 9Z-isomer via the C15 + C5 route.

  使用一种新方法，以交叉复分解反应为关键步骤，从苯乙烯衍生物合成了两种芳香族类维生素A。测试了新的维甲酸类似物的生物活性。跨复分解反应还用于通过C 15  + C 5途径制备视黄酸乙酯及其9 Z-异构体。