dec-1-en-6-yne | 161389-74-8

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: dec-1-en-6-yne
• CAS: 161389-74-8
• 化学式: C₁₀H₁₆
• 分子量: 136.237
• InChiKey: RWDDFFYUIZOREL-UHFFFAOYSA-N

物化性质

• 沸点：
  174.5±19.0 °C(Predicted)
• 密度：
  0.792±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  氯甲基苯砜 、 dec-1-en-6-yne 在 正丁基锂 、 二氯二茂锆 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以84%的产率得到1-(2-((E)-2-butylidenecyclopentyl)ethylsulfonyl)benzene
  参考文献：
  名称：

  Ring expansion of 5- to 6-member zirconacycles by carbenoid insertion

  摘要：

  A wide range of carbenoids (1-lithio-1-halo species), including those with alpha-SiR3, OEt, SPh, SO2Ph, P(O)(OEt)(2), and CN substituents, insert into 5-member zirconacycles (saturated and unsaturated, mono- and bi-cyclic) to afford functionalized 6-member zirconacycles. 1-Lithio-1-haloalkenes insert to afford 6-member zirconacycles with an alkylidene substituent next to the metal. Unexpected double insertion of some carbenoids, and evidence for endocylic beta-hydride transfer processes provide additional mechanistic interest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.056
• 作为产物：
  描述：

  2-bromo-1-decen-6-yne 在 叔丁基锂 作用下， 生成 dec-1-en-6-yne 、 1-[(E)-butylidene]-2-methylenencyclopentane
  参考文献：
  名称：

  Cycloisomerization of Acetylenic Vinyllithiums: Sequential Anionic Cyclization-Cycloaddition as a Route to Polycyclic Ring Systems

  摘要：

  Acetylenic vinyllithiums, generated by low-temperature metal-halogen exchange, were found to undergo facile 5-exo-dig cyclization to afford isomerically pure conjugated 1,3-bis-exocyclic dienes which serve as reactive precursors to complex polycyclic materials through subsequent Diels-Alder methodology.

  DOI：

  10.1021/jo00099a010

文献信息

• Tandem Insertion of Halocarbenoids and Lithium Acetylides into Zirconacycles: A Novel Rearrangement to Zirconium Alkenylidenates by β-Addition to an Alkynyl Zirconocene
  作者：Jozef Stec、Emma Thomas、Sally Dixon、Richard J. Whitby

  DOI：10.1002/chem.201002962

  日期：2011.4.18

  Tandem insertion of 1,1‐dihalo‐1‐lithio species (halocarbenoids) and lithium alkynides into zirconacyclopentenes and zirconcyclopentanes affords carbocyclic products in high yields via an unusual rearrangement that probably involves addition of an organolithium species to the β‐position of a zirconium–alkyne complex to give an alkenylidene–zirconate species. A wide variety of cyclopentanoid organic

  将1,1–二卤代1–硫代化合物（卤代类固醇）和炔属锂串联插入到氧化锆环戊烯和锆环戊烷中可以通过不寻常的重排提供高收率的碳环产物，该重排可能涉及将有机锂物种添加到锆的β位上。炔烃复合物，可得到烯基-锆酸酯。使用这种多组分偶联剂，可以高产率快速组装各种各样的环戊烷类有机结构。在某些情况下，主要的副反应是β-氢化物消除中间的环戊基或环戊烯基锆茂。
• A Rearrangement to a Zirconium–Alkenylidene in the Insertion of Dihalocarbenoids and Acetylides into Zirconacycles
  作者：Emma Thomas、Sally Dixon、Richard J Whitby

  DOI：10.1002/anie.200602822

  日期：2006.10.27
• Small Molecule Agonists of the Orphan Nuclear Receptors Steroidogenic Factor-1 (SF-1, NR5A1) and Liver Receptor Homologue-1 (LRH-1, NR5A2)
  作者：Richard J. Whitby、Jozef Stec、Raymond D. Blind、Sally Dixon、Lisa M. Leesnitzer、Lisa A. Orband-Miller、Shawn P. Williams、Timothy M. Willson、Robert Xu、William J. Zuercher、Fang Cai、Holly A. Ingraham

  DOI：10.1021/jm1014296

  日期：2011.4.14

  The crystal structure of LRH-1 ligand binding domain bound to our previously reported agonist 3-(E-oct-4-en-4-y1)-1-phenylamino-2-phenyl-cis-bicyclo[3.3.0]oct-2-ene 5 is described. Two new classes of agonists in which the bridgehead anilino group from our first series was replaced with an alkoxy or 1-ethenyl group were designed, synthesized, and tested for activity in a peptide recruitment assay. Both new classes gave very active compounds, particularly against SF-1. Structure-activity studies led to excellent dual-LRH-1/SF-1 agonists (e.g., RJW100) as well as compounds selective for LRH-1 (RJW101) and SF-1 (RJW102 and RJW103). The series based on 1-ethenyl substitution was acid stable, overcoming a significant drawback of our original bridgehead anilino-substituted series. Initial studies on the regulation of gene expression in human cell lines showed excellent, reproducible activity at endogenous target genes.