4-phenyl-2-(pyridin-2-yl)but-3-yn-2-ol | 55690-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-phenyl-2-(pyridin-2-yl)but-3-yn-2-ol
• 英文别名: alpha-Methyl-alpha-(phenylethynyl)-2-pyridinemethanol；4-phenyl-2-pyridin-2-ylbut-3-yn-2-ol
• CAS: 55690-01-2
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: KLEPIYFAJPBWKT-UHFFFAOYSA-N

物化性质

• 沸点：
  387.4±37.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenyl-2-(pyridin-2-yl)but-3-yn-2-ol 在 N-溴代丁二酰亚胺(NBS) 、 N-(benzyloxycarbonyl)-L-cysteine ethyl ester 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到2-bromo-1-hydroxy-1-methyl-3-phenyl-1H-indolizin-4-ium chloride
  参考文献：
  名称：

  通过5-和6-endo-dig环化反应对含硫肽进行简单的功能化

  摘要：

  我们提出了一种简单方便的方法，可通过使用N-氯代琥珀酰亚胺从含有S–S或S–H键的肽中生成亚磺基亲电子试剂。相应的亚硫基亲电试剂进一步用于5-和6-内-挖-环化反应，生成吲哚鎓盐，吲哚，苯并[b]呋喃，聚芳烃（PAH）和异香豆素，以及带有谷胱甘肽部分的喹啉酮。PAH衍生物可用作选择性荧光染料，以可视化活细胞中的脂质滴。

  DOI：

  10.1055/a-1343-5607
• 作为产物：
  描述：

  2-乙酰基吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 4-phenyl-2-(pyridin-2-yl)but-3-yn-2-ol
  参考文献：
  名称：

  Palladium-catalyzed construction of poly-substituted indolizinones

  摘要：

  We have developed a highly efficient one-pot approach to poly-substituted indolizinones from tertiary propargylic alcohols by using a palladium-catalyzed domino reaction. This reaction is proposed to proceed via successive aminopalladation, reductive elimination, and 1,2-shift. While our previous effort to the same skeleton via 2-iodoindolizinones selected alpha,beta-unsaturated esters, terminal acetylenes, or boronic acids as coupling partners, this strategy introduces new functional groups at the C2 position of indolizinone core with (hetero)aryl halides or diallyl carbonate, expanding the substrate scope for decoration at the C2 site. Furthermore, a new preparation route to tertiary propargylic alcohols for this study is described to rapidly diversify the molecular framework. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.091

文献信息

• Indolizinones as synthetic scaffolds: fundamental reactivity and the relay of stereochemical information
  作者：Alison R. Hardin Narayan、Richmond Sarpong

  DOI：10.1039/c1ob06423a

  日期：——

  Indolizinones are under-explored N-heterocycles that react with exquisite chemo- and stereoselectivity. An exploration of the fundamental reactivity of these azabicycles demonstrates the potential to relay stereochemical information from the ring-fusion to newly formed stereocenters on the bicyclic core. The indolizinone diene undergoes selective hydrogenation and readily participates in Diels–Alder cycloadditions as well as ene reactions. The vinylogous amide embedded in the five-membered ring is resistant to reaction when the diene is in place. However, removal of the diene allows for diastereoselective hydrogenation of, and 1,4-additions to, the vinylogous amide. These fundamental reactions with indolizinones have provided a structurally diverse array of products that hold promise in the context of natural product synthesis.

  吲哚嗪酮是一类研究不足的N-杂环化合物，它们以出色的化学选择性和立体选择性进行反应。对这些氮杂双环基础反应性的探索表明，它们能够将环融合中的立体化学信息传递到双环核上新生成的立体中心。吲哚嗪酮二烯经历选择性氢化反应，并容易参与Diels-Alder环加成反应以及烯反应。嵌入五元环中的乙烯基酰胺在二烯存在时不易发生反应。然而，去除二烯则允许对乙烯基酰胺进行立体选择性氢化和1,4-加成反应。这些与吲哚嗪酮的基础反应产生了结构多样化的产物，这些产物在天然产物合成领域具有潜在的应用价值。
• Efficient solvent-free synthesis of tertiary propargylic alcohols from arylacetylenes and ketones promoted by tert-BuOK
  作者：Shufeng Chen、Fang Yuan、Haiying Zhao、Baoguo Li

  DOI：10.1007/s11164-012-0765-9

  日期：2013.7

  A mild and efficient method for the alkynylation of arylacetylenes with ketones promoted by tert-BuOK under solvent-free conditions was developed. The present green synthesis was applicable to many kinds of aromatic and aliphatic ketones providing good to excellent yields of tertiary propargylic alcohols. A mild and efficient method for the alkynylation of arylacetylenes with ketones promoted by tert-BuOK under solvent-free conditions was developed. The present green synthesis was applicable to many kinds of aromatic and aliphatic ketones providing good to excellent yields of tertiary propargylic alcohols.

  开发了一种温和且高效的方法，使用叔丁醇钾在无溶剂条件下对芳基乙炔与酮进行炔基化。该绿色合成方法适用于多种芳香和脂肪族酮，能提供良好至优异的三级炔基醇产率。
• Peptide Functionalization Through the Generation of Selenocysteine Electrophile
  作者：Pavel Arsenyan、Sindija Lapcinska、Anna Ivanova、Jelena Vasiljeva

  DOI：10.1002/ejoc.201900907

  日期：2019.8.15

  The first example of a strategy for peptide functionalization through the generation of selenocysteine electrophile in 5‐ and 6‐endo‐dig cyclization reactions is reported. This simple approach allows bio‐conjugation of selenocystine‐based peptides.

  报道了在5和6位内切地环化反应中通过生成硒代半胱氨酸亲电试剂实现肽功能化的策略的第一个实例。这种简单的方法可以使基于硒代半胱氨酸的肽进行生物缀合。
• Hydroxy group-enabled highly regio- and stereo-selective hydrocarboxylation of alkynes
  作者：Chaofan Huang、Hui Qian、Wanli Zhang、Shengming Ma

  DOI：10.1039/c8sc05743e

  日期：——

  Here we present an example of utilizing hydroxy groups for regioselectivity control in the addition reaction of alkynes—a highly efficient Pd-catalyzed syn-hydrocarboxylation of readily available 2-alkynylic alcohols with CO in the presence of alcohols with an unprecedented regioselectivity affording 3-hydroxy-2(E)-alkenoates. The role of the hydroxy group has been carefully studied. The synthetic

  在这里，我们展示了一个在炔烃的加成反应中利用羟基进行区域选择性控制的例子——在醇的存在下，一种高效的 Pd 催化的 2-炔醇与 CO 的顺式加氢羧化反应，具有前所未有的区域选择性，提供 3-羟基-2( E )-链烯酸酯。羟基的作用已被仔细研究过。产品的合成潜力也得到了证明。
• Synthesis of new cyclazines and 4,5-diaryl-1<i>H</i>-pyrrol-3(2<i>H</i>)-one units in discoipyrroles from indolizinone-DMAD cycloadducts
  作者：Jais Kurian、Muraleedharan Kannoth M.

  DOI：10.1039/c9ob01655d

  日期：——

  access to 3',8a-dihydrocyclopenta[hi]indolizin-8a-ol and 1H-pyrrol-3(2H)-one in good yields. The former skeleton is a precursor to cyclazines with nitrogen on the periphery, a hitherto un-accessed 10-π system. Their formation involves initial [4 + 2] or [8 + 2] modes of cycloadditions; the retro-Diels Alder reaction of the [4 + 2] cycloadduct leads to 1H-pyrrol-3(2H)-one, whereas [8 + 2] addition followed

  吲哚嗪酮与乙酰二羧酸二甲酯的反应以良好的收率直接获得了3'，8a-二氢环戊基吲哚嗪-8a-ol和1H-吡咯-3（2H）-。前者的骨架是环嗪的前体，环上有氮，这是迄今尚未得到的10-π系统。它们的形成涉及初始的[4 + 2]或[8 + 2]环加成反应模式。[4 + 2]环加合物的Diels Alder逆反应生成1H-吡咯-3（2H）-1，而[8 + 2]加π重组后形成氮杂腈。取代基对产物分布的影响分析表明，C3-芳基环上的给电子基团显着促进了氮杂三环的形成。用HBF4处理这些氮杂三环化合物之一（3c）导致形成相应的10e-芳香族物质，该物质通过NMR光谱检测。此外，通过正常的逆Diels Alder途径形成1H-吡咯-3（2H）-一个骨架被用于Discooipyrrole C的全合成，这是对抗肺癌的新途径。