3-Methoxy-3-phenyl-1,4-pentadiin | 51110-57-7

• 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: 3-Methoxy-3-phenyl-1,4-pentadiin
• 英文别名: 3-phenyl-3-methoxypenta-1,4-diyne；(1-ethynyl-1-methoxy-prop-2-ynyl)-benzene；3-Methoxypenta-1,4-diyn-3-ylbenzene
• CAS: 51110-57-7
• 化学式: C₁₂H₁₀O
• 分子量: 170.211
• InChiKey: WNYPFWKPGKZOAK-UHFFFAOYSA-N

物化性质

• 沸点：
  254.5±40.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Methoxy-3-phenyl-1,4-pentadiin 、 dibutylstannane 以 甲基环己烷 为溶剂， 以68%的产率得到1,1-di-n-butyl-4-phenyl-4-methoxy-1,4-dihydrostannane
  参考文献：
  名称：

  Maerkl, G.; Kneidl, F., Angewandte Chemie, 1973, vol. 85, p. 990 - 991

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(trimethylsilyl)-1-phenyl-2-propyn-1-one 在 正丁基锂 、 乙基溴化镁 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 3-Methoxy-3-phenyl-1,4-pentadiin
  参考文献：
  名称：

  Synthesis and stereochemical resolution of functional [5]pericyclynes

  摘要：

  Three different kinds of ring carbo-mers of [5]cyclitol ethers were targeted as challenging examples of functional [5]pericyclynes. Three tertiary pentaaryl-carbo-[5]cyclitol methyl ethers were synthesized through a [11 + 4] ring-closing double addition of triphenyl- and tri-p-anisyl-undecatetrayn-diides to dibenzoyl acetylene. These compounds, obtained as oily mixtures of stereoisomers, are stable and can behave as acetylenic ligands of one or two Co-2(CO)(6) units. NMR analysis reveals that the broad diasteroisomeric dispersity of a triether, is consistently reduced in the symmetrized pentaether. Three bis-secondary triaryl-carbo-[5]cyclitol methyl ethers with adjacent CH(OR) vertices were synthesized through a similar [11 + 4] ring-closing process, where the same tetrayn-diides add to both the carbaldehyde ends of the (eta(2)-OCH-C=C-CHO)Co-2(CO)(6) complex. Despite the possibility of tautomeric isomerization, the occurrence of two adjacent bis-propargylic carbinol vertices does not diminish the stability of the [5]pericyclyne framework. Finally, two bis-secondary carbo-[5]cyclitol methyl ethers with non-adjacent CH(OH) vertices were synthesized through an alternative [10 + 5] ring-closing process. The bis-secondary carbo-[5]cyclitols are regarded as isohypsic equivalents of the challenging [C,C](5)carbo-cyclopentadienyl cation. A diphenyl-hexaoxy-[5]pericyclyne with two non-adjacent secondary carbinol vertices was also prepared through a [10 + 5] ring-closing strategy: this molecule is an isohypsic equivalent of the previously calculated zwitterionic carbo-cyclopentadien one, which could be observed as a DCI/NH3-MS fragment after treatment with SnCl2/HCl. Analytical HPLC showed that the C-11 triphenyl-undecatetrayne precursor of the [11 + 4] strategy was obtained as a statistical 1:2:1 mixture of the three possible diastereoisomers. Semi-preparative HPLC allowed for the resolution of this mixture. The pure major diastereoisomer was employed to prepare a partly resolved sample of pentamethoxy-pentaphenyl-[5]pericyclyne. Analytical HPLC showed that the latter corresponds to the statistical distribution of the expected three residual diastereoisomers. Semi-preparative HPLC finally afforded samples of diastereoisomerically pure pentamethoxy[5]pericyclyne as crystalline solids. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.052

文献信息

• Functional [6]Pericyclynes: Synthesis through [14+4] and [8+10] Cyclization Strategies
  作者：Catherine Saccavini、Christine Tedeschi、Luc Maurette、Christine Sui-Seng、Chunhai Zou、Michèle Soleilhavoup、Laure Vendier、Remi Chauvin

  DOI：10.1002/chem.200601191

  日期：2007.6.4

  used [11+7] strategy, the [14+4] and [8+10] strategies were thus explored. They proved to be efficient, affording seven novel hexaoxy[6]pericyclynes corresponding to six different substitution patterns. These compounds were obtained in 7-15 steps as mixtures of stereoisomers. Thus, by using dibenzoylacetylene as the C(4) electrophile, a [14+4] strategy allowed the synthesis of two hexaphenyl representatives

  对合成新型碳苯衍生物的可能策略的关键分析表明，制备[[18] -n] + n]途径有几种制备六氧基[6]-环炔前体的方法。除了先前尝试的[9 + 9]对称方案（n = 9）外，最先选择的策略是n = 1、4、7、10、13和16的那些。含有（19-n）/ 3个三键的C（18-n）ω-双末端的低聚炔，具有含有（n-1）/ 3个三键的C（n）ω-二羰基的ω-双的低聚炔。为了补充先前使用的[11 + 7]策略，因此探索了[14 + 4]和[8 + 10]策略。他们被证明是有效的，提供了对应于六个不同取代模式的七个新颖的六氧[6]环芳烃。这些化合物以7-15个步骤的形式以立体异构体的混合物形式获得。因此，通过使用二苯甲酰基乙炔作为C（4）亲电试剂，[14 + 4]策略允许合成具有两个或四个游离甲醇顶点的两个六苯基代表。该方法还提供了四苯基代表，其中两个剩余的甲氧基顶点被两个炔基或一个4-茴香基和一
• Merz,A., Angewandte Chemie, 1973, vol. 85, p. 868 - 869
  作者：Merz,A.

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.4, 1.2.2.1.5.4, page 106 - 110
  作者：

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.3, 1.1.6.1.3, page 105 - 108
  作者：

  DOI：——

  日期：——
• Maerkl, Gottfried; Liebl, Rainer; Baier, Horst, Liebigs Annalen der Chemie, 1981, # 9, p. 1610 - 1632
  作者：Maerkl, Gottfried、Liebl, Rainer、Baier, Horst

  DOI：——

  日期：——