6-(tetrahydro-2H-pyran-2-yloxy)hex-4-ynal | 138886-63-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 6-(tetrahydro-2H-pyran-2-yloxy)hex-4-ynal
• 英文别名: 6-[(Oxan-2-yl)oxy]hex-4-ynal；6-(oxan-2-yloxy)hex-4-ynal
• CAS: 138886-63-2
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: FMTSLBRTJWSREI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(tetrahydro-2H-pyran-2-yloxy)hex-4-ynal 在 sodium chlorite 、 sodium dihydrogenphosphate 、 异丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 生成
  参考文献：
  名称：

  Targeting a Novel KRAS Binding Site: Application of One-Component Stapling of Small (5–6-mer) Peptides

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c01334
• 作为产物：
  描述：

  1-(tert-butyldimethylsilyloxy)-4-pentyne 在 sodium tetrahydroborate 、 正丁基锂 、 草酰氯 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 6-(tetrahydro-2H-pyran-2-yloxy)hex-4-ynal
  参考文献：
  名称：

  Targeting a Novel KRAS Binding Site: Application of One-Component Stapling of Small (5–6-mer) Peptides

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c01334

文献信息

• [1.3], [3.3] and Tandem [1.3]–[3.3] rearrangements of 11- and 12-membered trienolides
  作者：Khalid M. Khan、David W. Knight

  DOI：10.1039/c39910001699

  日期：——

  The bis-O-silyl enolates 5 derived from lactones 4 rearrange via a tandem [1.3]–[3.3] mechanism leading to the cyclopentane acids 8, whereas the higher homologue 13 is similarly converted into the cyclodecene 15 by a [1.3] process; by contrast, O-silyl enolates of the less substituted lactones 21 and 25 undergo exclusively [3.3] rearrangements.

  衍生自内酯 4 的双-O-甲硅烷基烯醇化物 5 通过串联 [1.3]→[3.3] 机制重排，生成环戊烷酸 8，而高级同系物 13 类似地通过 [1.3] 转化为环癸烯 15过程;相比之下，较少取代的内酯21和25的O-甲硅烷基烯醇化物仅发生[3.3]重排。
• Synthesis and Cytotoxicity of Leinamycin Antibiotic Analogues
  作者：Ákos Szilágyi、Ferenc Fenyvesi、Orsolya Majercsik、István F. Pelyvás、Ildikó Bácskay、Pálma Fehér、Judit Váradi、Miklós Vecsernyés、Pál Herczegh

  DOI：10.1021/jm060471h

  日期：2006.9.1

  A simple synthesis of 1,2-dithiolan-3-ones from alpha,beta-unsaturated thiophenyl esters is reported. Introduction of the biologically active 1,2-dithiolan-3-one-1-oxide moiety of leinamycin into aldehydo-D-arabinose 11, the uridine derivative 16, and the deoxythymidine 21 was established. An extended bioactive part of leinamycin carrying a carbon-carbon triple bond was also synthesized. All of these analogues of leinamycin showed cytotoxic activity against HeLa3 tumor cells. Interestingly, the lipophilic, silyl group-containing derivatives proved to be more active than the hydrophilic counterparts.
• A Synthesis of (−)-Mintlactone
  作者：Roderick W. Bates、S. Sridhar

  DOI：10.1021/jo801433f

  日期：2008.10.17

  Mintlactone is synthesized in a concise and efficient way by using a highly diastereoselective intramolecular propargylic Barbier reaction, followed by an allenol cyclocarbonylation. Tin(II) chloride is found to be the most effective reagent for the Barbier reaction.
• Targeting a Novel KRAS Binding Site: Application of One-Component Stapling of Small (5–6-mer) Peptides
  作者：Gabriele Fumagalli、Rodrigo J. Carbajo、J. Willem M. Nissink、Jonathan Tart、Rongxuan Dou、Andrew P. Thomas、David R. Spring

  DOI：10.1021/acs.jmedchem.1c01334

  日期：2021.12.9