1,1-diphenyl-3-(trimethylsilyl)prop-2-yn-1-ol | 73502-43-9

• 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: 1,1-diphenyl-3-(trimethylsilyl)prop-2-yn-1-ol
• 英文别名: 1,1-diphenyl-3-trimethylsilyl-2-propyn-1-ol；1,1-diphenyl-3-trimethylsilyl-2-propynol；1,1-Diphenyl-3-trimethylsilylprop-2-yn-1-ol
• CAS: 73502-43-9
• 化学式: C₁₈H₂₀OSi
• 分子量: 280.442
• InChiKey: PWULSVNEZMOZFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  397.2±42.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1-diphenyl-3-(trimethylsilyl)prop-2-yn-1-ol 在 氢氧化钾 、 次溴酸钾 、 potassium carbonate 作用下， 以 甲醇 、 正戊烷 为溶剂， 反应 84.0h， 生成 1-溴-3,3-二苯基-1-丙炔-3-醇
  参考文献：
  名称：

  Saalfrank, Rolf W.; Welch, Andreas; Haubner, Martin, Liebigs Annalen, 1996, # 2, p. 171 - 181

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰氯 在 aluminum (III) chloride 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1,1-diphenyl-3-(trimethylsilyl)prop-2-yn-1-ol
  参考文献：
  名称：

  Design of pH responsive clickable prodrugs applied to histone deacetylase inhibitors: A new strategy for anticancer therapy

  摘要：

  The aim of this study was to develop clickable prodrugs bearing a tunable pH responsive linker designed for acidic pH-mediated release of histone deacetylase inhibitors. HDACi are an important class of molecules belonging to the epigenetic modulators used for innovative cancer strategies. The behavior of these prodrugs was determined by a bioluminescence resonance energy transfer assay in living tumor cells. This work demonstrated that this innovative type of clickable prodrugs entered cancer cells and showed restored anti proliferative properties attributed to the effective release of the HDAC inhibitors. A correlation between kinetic studies, dose responses, and biological activities was obtained, making such clickable prodrugs good candidates for new strategies in epigenetic-oriented anticancer therapies. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejpb.2013.03.006

文献信息

• The Intricate Assembling of<i>gem</i>-Diphenylpropargylic Units
  作者：Valérie Maraval、Carine Duhayon、Yannick Coppel、Remi Chauvin

  DOI：10.1002/ejoc.200800711

  日期：2008.10

  While optimized procedures for selective propargylic – versus allenic – attack (in particular by alkynylsilanes) have proven to be compatible with many substitution patterns at the propargylic center, the case of diarylpropargyl electrophiles has remained problematic. The intrinsic reactivity of 1,1-diphenylpropargylic alcohols [R–C≡C–C(Ph2)OH (R = TMS, H, Me)] in the presence of various acids (and

  虽然选择性炔丙基 - 与丙二烯 - 攻击（特别是炔基硅烷）的优化程序已被证明与炔丙基中心的许多取代模式兼容，但二芳基炔丙基亲电试剂的情况仍然存在问题。1,1-二苯基炔丙醇 [R–C≡C–C(Ph2)OH (R = TMS, H, Me)] 在各种酸存在下（并且不存在其他亲核试剂）的内在反应性因此被证明系统地调查。单苯基类似物 [R–C≡C–CH(Ph)OH] 可提供预期的双（苯基炔丙基）醚，而二苯基形式经过复杂但选择性很高的过程以提供各种结构类型：取决于所使用的酸，二烯，获得了丙炔、茚基丙二烯、茚满酮或稠合的四环和五环。当在炔基硅烷存在下进行反应时，炔基硅烷能够起到竞争亲核试剂的作用，预期的炔丙基取代产物——二炔基二苯基甲烷或其异构体——从未观察到。然而，迄今为止未知的简单碳氢化合物二乙炔基和二丙炔基二苯基甲烷可以通过四步序列以低收率获得，包括亚丙叉基和炔基钌中间体。 (© Wiley-VCH
• Waste-Free Catalytic Propargylation/Allenylation of Aryl and Heteroaryl Nucleophiles and Synthesis of Naphthopyrans
  作者：J. McCubbin、Costa Nassar、Oleg Krokhin

  DOI：10.1055/s-0030-1260146

  日期：2011.10

  pyrroles, as well as methoxy-substituted benzenes and naphthalenes. Reaction with 2-naphthol affords substituted naphthopyrans as products. Preliminary evidence suggests a Friedel-Crafts-like substitution mechanism, which occurs via an in situ generated carbocation. organocatalysis - boronic acids - propargylic alcohols - Friedel-Crafts reaction

  已经开发了用富电子芳族碳环和杂环取代炔丙醇的通用方法。该反应在简单，温和的条件下进行，并使用廉价的环境友好且可回收的芳基硼酸催化剂全氟苯基硼酸，产生水作为唯一的副产物。对于炔丙基或烯丙基取代的产物，包括呋喃，吲哚和吡咯，以及甲氧基取代的苯和萘，观察到高收率和选择性。与2-萘酚反应得到取代的萘并吡喃类产物。初步证据表明，Friedel-Crafts样取代机制是通过原位生成的碳正离子发生的。 有机催化-硼酸-炔丙醇-Friedel-Crafts反应
• A Versatile and Highly Efficient Method for 1-Chlorination of Terminal and Trialkylsilyl-Protected Alkynes
  作者：Nurbey Gulia、Bartłomiej Pigulski、Marta Charewicz、Sławomir Szafert

  DOI：10.1002/chem.201303680

  日期：2014.3.3

  A highly efficient one‐pot procedure for the preparation of 1‐chloroalkynes and 1‐chlorobutadiynes from terminal and trialkylsilyl‐protected precursors is reported. This convenient reaction, proceeding under mild conditions, utilizes N‐chlorosuccinimide as the chlorinating agent and tolerates a range of functional groups.

  报道了1-氯炔和从终端和三烷基甲硅烷保护的前体1-chlorobutadiynes制备A高效单罐方法。这种方便的反应，在温和的条件下继续进行，利用Ñ氯代琥珀酰亚胺作为氯化剂和容忍范围的官能团。
• Efficient Synthesis and Antibacterial Activities of Some Novel 1,2,3-Triazoles Prepared from Propargylic Alcohols and Benzyl Azides
  作者：Rahman Hosseinzadeh、Mohammadreza Khadem Abolfazli、Mojtaba Mohseni、Maryam Mohadjerani、Zahra Lasemi

  DOI：10.1002/jhet.1680

  日期：2014.9

  A simple and effective procedure for regioselective preparation of 1,2,3‐triazoles from benzyl azides and propargylic alcohols is described using CuSO4.5H2O and sodium ascorbate. To screen the antibacterial activity of some newly synthesized triazole derivatives, minimum inhibitory concentration of 3d and 3k was evaluated against gram positive Staphylococcus aureus and Bacillus subtilis and gram negative

  描述了一种使用CuSO 4 .5H 2 O和抗坏血酸钠从苄基叠氮化物和炔丙基醇区域选择性制备1,2,3-三唑的简单有效方法。为了筛选一些新合成的三唑衍生物的抗菌活性，评估了对革兰氏阳性金黄色葡萄球菌和枯草芽孢杆菌以及革兰氏阴性大肠杆菌和铜绿假单胞菌的最低抑菌浓度3d和3k。
• Synthesis of Allenes via Gold-Catalyzed Intermolecular Reaction of Propargylic Alcohols and Aromatic Compounds
  作者：Cheng-Fu Xu、Mei Xu、Liu-Qing Yang、Chuan-Ying Li

  DOI：10.1021/jo300147u

  日期：2012.3.16

  Functionalized allenes are efficiently synthesized in moderate to high yield from gold-catalyzed intermolecular reaction of propargylic alcohols and aromatic compounds. The user-friendly process could be conducted under mild reaction conditions with easily accessible starting materials.

  通过金催化的炔丙醇和芳族化合物的分子间反应，可以中等至高收率有效地合成官能化的烯。用户友好的过程可以在温和的反应条件下用容易获得的原料进行。