Benzenemethanol,a-[3-methoxy-3-phenyl-5-(trimethylsilyl)-1,4-pentadiynyl]-a-[(trimethylsilyl)ethynyl]- | 801287-65-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: Benzenemethanol,a-[3-methoxy-3-phenyl-5-(trimethylsilyl)-1,4-pentadiynyl]-a-[(trimethylsilyl)ethynyl]-
• 英文别名: 1,8-bis(trimethylsilyl)-6-methoxy-3,6-diphenylocta-1,4,7-triyn-3-ol
• CAS: 801287-65-0
• 化学式: C₂₇H₃₂O₂Si₂
• 分子量: 444.721
• InChiKey: YRQHYJACOVYODP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Benzenemethanol,a-[3-methoxy-3-phenyl-5-(trimethylsilyl)-1,4-pentadiynyl]-a-[(trimethylsilyl)ethynyl]- 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 3,6-dimethoxy-3,6-diphenylocta-1,4,7-triyne
  参考文献：
  名称：

  六芳基-碳-苯的再研究：一种新颖的合成路线，晶体学数据和电化学行为的前景†

  摘要：

  一种改进的12步合成路线和hexaphenyl-的全面表征碳氮化-苯（4，8％）和p -双-3,5-二-叔丁基苯基同源物（11，4％），中描述。该碳氮化-苯参考4现在精确地处于晶体状态通过X射线衍射分析中的手性，空间群描述P 2 1 2 1 2 1，和相比于较少对称衍生物11表现出中心对称填料。根据循环伏安法，六芳基-碳-苯4和11既可以作为可逆的强电子受体，也可以作为标准的电子给体，各自的电位分别为-0.73±1 V和+1.17±2 V / SCE。由于其极低的溶解度，使用“湿法”制造的11层固态膜具有研究电荷传输特性的最初观点，被发现具有较高的粗糙度。

  DOI：

  10.1039/c7nj00028f
• 作为产物：
  描述：

  二(三甲基甲硅烷基)乙炔 在 aluminum (III) chloride 、 乙基溴化镁 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Benzenemethanol,a-[3-methoxy-3-phenyl-5-(trimethylsilyl)-1,4-pentadiynyl]-a-[(trimethylsilyl)ethynyl]-
  参考文献：
  名称：

  六芳基-碳-苯的再研究：一种新颖的合成路线，晶体学数据和电化学行为的前景†

  摘要：

  一种改进的12步合成路线和hexaphenyl-的全面表征碳氮化-苯（4，8％）和p -双-3,5-二-叔丁基苯基同源物（11，4％），中描述。该碳氮化-苯参考4现在精确地处于晶体状态通过X射线衍射分析中的手性，空间群描述P 2 1 2 1 2 1，和相比于较少对称衍生物11表现出中心对称填料。根据循环伏安法，六芳基-碳-苯4和11既可以作为可逆的强电子受体，也可以作为标准的电子给体，各自的电位分别为-0.73±1 V和+1.17±2 V / SCE。由于其极低的溶解度，使用“湿法”制造的11层固态膜具有研究电荷传输特性的最初观点，被发现具有较高的粗糙度。

  DOI：

  10.1039/c7nj00028f

文献信息

• Synthesis and stereochemical resolution of functional [5]pericyclynes
  作者：Luc Maurette、Christine Tedeschi、Emmanuelle Sermot、Michèle Soleilhavoup、Fatima Hussain、Bruno Donnadieu、Remi Chauvin

  DOI：10.1016/j.tet.2004.07.052

  日期：2004.10

  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.