3-(4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one | 608533-22-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one
• CAS: 608533-22-8
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: HFLFPKIHYFQANH-UHFFFAOYSA-N

物化性质

• 熔点：
  154-156 °C
• 沸点：
  490.8±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到[5-(4-methoxyphenyl)-2H-triazol-4-yl]-(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation

  摘要：

  In the chalcone scaffold, it is thought that the double bond is an important structural linker but it is likely not essential for the interaction with tubulin. Yet, it may be a potential site of metabolic degradation and interaction with biological nucleophiles. In this letter, we have replaced this olefinic portion of chalcones with two metabolically stable and chemically inert heterocyclic rings, namely triazole or tetrazole. Yet, our biologic data suggest that, unlike in other antitubulinic structures, the olephinic ring might not be merely a structural linker. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.113
• 作为产物：
  描述：

  3-(4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以6.13 g的产率得到3-(4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one
  参考文献：
  名称：

  Iodine-Induced Reaction Cascades for the Rapid Construction of Variously Substituted Benzothiophenes

  摘要：

  Readily accessible propynols with a 2-thioxyphenyl substituent selectively undergo 5-exo-iodocyclization followed by tandem rearrangement and elimination or substitution processes to give selective access to either 2-acyl- or 2-(1-iodoalkeny)-benzo[b]thiophene systems.

  DOI：

  10.1021/ol035663a

文献信息

• A Reductive-Coupling plus Nazarov Cyclization Sequence in the Asymmetric Synthesis of Five-Membered Carbocycles
  作者：Daniel J. Kerr、Jonathan M. White、Bernard L. Flynn

  DOI：10.1021/jo100736p

  日期：2010.11.5

  Palladium-mediated hydrostannylation of alkynoyl compounds is combined with Stille-Scott cross-coupling (reductive-coupling) to give one-pot access to divinyl and aryl vinyl ketones, which undergo Nazarov cyclization to give cyclopentenones upon treatment with acid. This reaction sequence has been studied with a variety of different substitution patterns, including the use of oxazolidinone auxiliaries to achieve torquoselectivity in the Nazarov cyclization. Through a combination of good yields and moderate to good levels of stereochemical induction, this approach affords efficient, convergent, and asymmetric access to a variety of different cyclopentanoid systems.
• Dissecting Alkynes: Full Cleavage of Polarized C≡C Moiety via Sequential Bis-Michael Addition/Retro-Mannich Cascade
  作者：Saumya Roy、Maria P. Davydova、Runa Pal、Kerry Gilmore、Genrikh A. Tolstikov、Sergei F. Vasilevsky、Igor V. Alabugin

  DOI：10.1021/jo201259j

  日期：2011.9.16

  The reaction of diaryl ketoalkynes with 1,2-diamino ethane leads to e full scission of the triple bond with the formation of acetophenone and imidazoline fragments. In this transformation, one of the alkyne carbons undergoes formal reduction with the formation of three C-H bonds, whereas the other carbon undergoes formal oxidation via the formation of three C-N bonds (one pi and two sigma). Computational analysis confirmed that the key fragmentation step proceeds via a six-membered TS in a concerted manner. Both amines are involved in the fragmentation: the N-H moiety of one amine transfers a proton to the developing negative charge at the enolate oxygen, while the other amine provides direct stereoelectronic assistance to the C-C bond cleavage via a hyperconjugative n(N)->sigma*(C-C) interaction.
• Kerr, Daniel J.; Metje, Christiane; Flynn, Bernard L., Chemical Communications, 2003, # 12, p. 1380 - 1381
  作者：Kerr, Daniel J.、Metje, Christiane、Flynn, Bernard L.

  DOI：——

  日期：——
• Reaction of α,β-alkynylketones with β-amino alcohols: pseudoephedrine- assisted cleavage of triple bond via formal internal redox process
  作者：Sergei F. Vasilevsky、Maria P. Davydova、Victor I. Mamatuyk、Nadezhda V. Pleshkova、Dmitry S. Fadeev、Igor V. Alabugin

  DOI：10.1016/j.mencom.2015.09.021

  日期：2015.9

  Reaction of 3-aryl-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ones with (+)-pseudoephedrine leads to products of alkyne moiety cleavage, namely, 1-(3,4,5-trimethoxyphenyl)ethanone and N-(1-hydroxy-1-phenylprop-2-yl)-N-methylbenzamides. In the course of the process one of alkyne carbons undergoes a formal reduction to a Me group, whereas the other one is oxidized to a C(O)NRR' moiety.
• The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4
  作者：Daniel J. Kerr、Ernest Hamel、M. Katherine Jung、Bernard L. Flynn

  DOI：10.1016/j.bmc.2007.02.006

  日期：2007.5

  A series of aryl- and aroyl-substituted chalcone analogues of the tubulin binding agent combretastatin A4 (1) were prepared, using a recently introduced one-pot palladium-mediated hydrostannylation-coupling reaction sequence. These chalcones were converted to indanones by Nazarov cyclisation, followed by oxidation to give the corresponding indenones. Indenones were also prepared using a palladium-mediated formal [3+2]-cycloaddition process between ortho-halobenzaldehydes and diarylpropynones. All compounds were assessed as inhibitors of tubulin polymerisation, but only E-31 had activity similar to that of 1. However, compound E-31 did not exhibit antiproliferative activity against the MCF-7 cell line. (c) 2007 Elsevier Ltd. All rights reserved.