trans-(2-phenylcyclopropyl)acetylene

• 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: trans-(2-phenylcyclopropyl)acetylene
• 英文别名: [(1R,2R)-2-ethynylcyclopropyl]benzene
• 化学式: C₁₁H₁₀
• 分子量: 142.2
• InChiKey: NTSXPVAFKWNQIA-MWLCHTKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  trans-(2-phenylcyclopropyl)acetylene 、 3,4-己二酮 在 acetylacetonatodicarbonylrhodium(l) 2-(二叔丁基膦)联苯 作用下， 以 四氢呋喃 为溶剂， 以54%的产率得到4-ethyl-4-hydroxy-6-trans-(2-phenylcyclopropyl)hex-5-yn-3-one
  参考文献：
  名称：

  Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones

  摘要：

  Several heterocycles such as furanones, pyrrolones, and indolizines, which are of pharmacological importance, are easily accessed via the Pt(II)-catalyzed heterocyclization/1,2-migration of propargylic ketols or hydroxy imine derivatives. This method sidesteps the challenges of traditional heteroaromatic oxygenation strategies such as regioselectivity and functional group tolerance in the syntheses of these heterocycles. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.103
• 作为产物：
  描述：

  (1R,2R)-2-苯基环丙烷甲醛 、 potassium carbonate 、 (1-重氮基-2-氧代丙基)膦酸二甲酯 在 乙酸乙酯 、 Brine 、 Sodium sulfate-III 、 crude product 、 silica gel 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以to give the sub-title compound (690 mg, 81%)的产率得到trans-(2-phenylcyclopropyl)acetylene
  参考文献：
  名称：

  BICYCLIC HETEROAROMATIC CARBOXAMIDE COMPOUNDS USEFUL AS PIM KINASE INHIBITORS

  摘要：

  本公开说明书描述了双环杂环芳香族羧酰胺衍生物，以及它们的组合物和使用方法。这些化合物抑制Pim激酶的活性，可用于治疗与Pim激酶活性相关的疾病，例如癌症和其他疾病。

  公开号：

  US20160009726A1

文献信息

• The addition of terminal alkynes to dimesitylfluorenylidenegermane
  作者：Nada Y. Tashkandi、Laura C. Pavelka、Margaret A. Hanson、Kim M. Baines

  DOI：10.1139/cjc-2013-0532

  日期：2014.6

  A variety of terminal alkynes were added to dimesitylfluorenylidenegermane, Mes₂Ge=CR₂ (where CR₂ = fluorenylidene). The addition of phenylacetylene and 1-hexyne to Mes₂Ge=CR₂ gave a germacyclohexene via a cycloaddition where the germene acts as the 4π component and the alkyne as the 2π component. Through the use of a mechanistic probe, trans-(2-phenylcyclopropyl)-acetylene, the reaction was postulated to proceed through a concerted [2+4] cycloaddition. The addition of ethoxyacetylene to the germene produced both a [2+2] cycloadduct, a germacyclobutene, and a [2+4] cycloadduct, a germacyclohexene. The results of this study are compared to the results of the addition of alkynes to Mes₂Ge=CHCH₂-t-Bu.

  将各种末端炔烃加入二间苯基芴亚基锗烯，Mes₂Ge=CR₂（其中CR₂ = 芴亚基）。苯基乙炔和1-己炔加入到Mes₂Ge=CR₂中，通过环加成反应形成了一种锗环己烯，其中锗烯充当4π组分，炔烃充当2π组分。通过使用一个机械探针，反式-(2-苯基环丙基)-乙炔，推测该反应通过一个协同的[2+4]环加成进行。将乙氧基乙炔加入到锗烯中产生了一个[2+2]环加成产物，一种锗环丁烯，以及一个[2+4]环加成产物，一种锗环己烯。这项研究的结果与将炔烃加入到Mes₂Ge=CHCH₂-t-Bu的结果进行了比较。
• Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones
  作者：Eric M. Bunnelle、Cameron R. Smith、Sharon K. Lee、Surendra W. Singaram、Allison J. Rhodes、Richmond Sarpong

  DOI：10.1016/j.tet.2008.02.103

  日期：2008.7

  Several heterocycles such as furanones, pyrrolones, and indolizines, which are of pharmacological importance, are easily accessed via the Pt(II)-catalyzed heterocyclization/1,2-migration of propargylic ketols or hydroxy imine derivatives. This method sidesteps the challenges of traditional heteroaromatic oxygenation strategies such as regioselectivity and functional group tolerance in the syntheses of these heterocycles. (C) 2008 Elsevier Ltd. All rights reserved.
• BICYCLIC HETEROAROMATIC CARBOXAMIDE COMPOUNDS USEFUL AS PIM KINASE INHIBITORS
  申请人：Incyte Corporation

  公开号：US20160009726A1

  公开（公告）日：2016-01-14

  The present disclosure describes bicyclic heteroaromatic carboxamide derivatives, as well as their compositions and methods of use. The compounds inhibit the activity of the Pim kinases, and are useful in the treatment of diseases related to the activity of Pim kinases including, e.g., cancer and other diseases.

  本公开说明书描述了双环杂环芳香族羧酰胺衍生物，以及它们的组合物和使用方法。这些化合物抑制Pim激酶的活性，可用于治疗与Pim激酶活性相关的疾病，例如癌症和其他疾病。