3-phenyl-1-(trimethylsilyl)penta-1,4-diyn-3-ol | 99048-51-8

• 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-phenyl-1-(trimethylsilyl)penta-1,4-diyn-3-ol
• 英文别名: 3-Phenyl-1-trimethylsilylpenta-1,4-diyn-3-ol
• CAS: 99048-51-8
• 化学式: C₁₄H₁₆OSi
• 分子量: 228.366
• InChiKey: JYGLIVLMZNIBOX-UHFFFAOYSA-N

物化性质

• 沸点：
  142-144 °C(Press: 4 Torr)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-phenyl-1-(trimethylsilyl)penta-1,4-diyn-3-ol 在 正丁基锂 、 乙基溴化镁 、 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 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-phenyl-1-(trimethylsilyl)penta-1,4-diyn-3-ol
  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 of the first 3,6,9,15,18,18-hexa-substituted-1,2,4,5,7,8,10,11,13,14,16,17-dodecadehydro[18]annulenes with D6h-symmetry
  作者：Yoshiyuki Kuwatani、Naoto Watanabe、Ikuo Ueda

  DOI：10.1016/0040-4039(94)02181-a

  日期：1995.1

  3,6,9,12,15,18-Hexaphenyl-1,2,4,5,7,8,10,11,13,14,16,17-dodecadehydro[18]annulene and related compounds have been synthesized. These compounds were found to be stable both in crystalline forms and chloroform solution at room temperature, to have aromatic character by the existance of a diamagnetic ring current on the basis of the nmr spectral data, and to conform to the D6h-symmetry group.

  合成了3,6,9,12,15,18-六苯基-1,2,4,5,7,8,10,11,13,14,16,17-十二烷基氢化[18]环戊烯和相关化合物。发现这些化合物是稳定的无论是在结晶形式，并在室温氯仿溶液，通过NMR谱数据的基础上形成的反磁性环电流是否存在等具有芳香性，和以符合d 6H -symmetry基。
• Synthesis, structure and properties of 3,9,15-tri- and 3,6,9,12,15,18-hexasubstituted dodecadehydro[18]annulenes (C18H3R3 and C18R6) with D6h-symmetry
  作者：Riho Suzuki、Hiroko Tsukuda、Naoto Watanabe、Yoshiyuki Kuwatani、Ikuo Ueda

  DOI：10.1016/s0040-4020(98)00011-8

  日期：1998.3

  3,9,15-Tris(p-tert-butylphenyl)dodecadehydro[18]annulene (6) and 3,6,9,12,15,18-hexa-substituted dodecadehydro[18]annulenes (7, 8, and 9) have been prepared. These compounds were shown to be heated up to 150 °C without decomposition. The molecular structure of 7 was determined by X-ray crystallography, which showed that 7 has a planar π-system with D6h-symmetry. The UV and NMR spectral data indicate

  3,9,15三（p -叔丁基苯基）dodecadehydro [18]轮烯（6）和3,6,9,12,15,18-六取代的dodecadehydro [18]轮烯（7,8，和9）已经准备好了。已显示这些化合物可加热至150°C，而不会分解。X射线晶体学确定7的分子结构，表明7具有D 6h对称性的平面π系统。UV和NMR光谱数据表明这四种化合物具有高的热稳定性和构象稳定性以及强的反磁性感应环电流。
• Bychkova, N. A.; Zotchik, N. V.; Motorina, Zh. N., Journal of general chemistry of the USSR, 1985, vol. 55, # 5, p. 990 - 995
  作者：Bychkova, N. A.、Zotchik, N. V.、Motorina, Zh. N.、Rubtsov, I. A.

  DOI：——

  日期：——
• 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.
• Substituent effect on reactions of ReH5(PMe2Ph)3 with propargyl alcohols
  作者：Guomei He、Jiangxi Chen、Herman Ho-Yung Sung、Ian Duncan Williams、Guochen Jia

  DOI：10.1016/j.ica.2020.120239

  日期：2021.4