(hept-1-en-6-yn-7-yl)cyclohexane | 195534-72-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (hept-1-en-6-yn-7-yl)cyclohexane
• 英文别名: Hept-6-en-1-ynylcyclohexane
• CAS: 195534-72-6
• 化学式: C₁₃H₂₀
• 分子量: 176.302
• InChiKey: AFOJQRNGBGNWII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  (hept-1-en-6-yn-7-yl)cyclohexane 在 碳酸氢钠 作用下， 反应 24.0h， 生成 2-cyclohexyl-3-((E)-oct-4-en-4-yl)-1-phenylamino-cis-bicyclo[3.3.0]oct-2-ene
  参考文献：
  名称：

  孤儿核受体肝受体homolog-1和类固醇生成因子1的小分子激动剂的鉴定。

  摘要：

  我们报告了取代的顺式-双环[3.3.0]-辛-2-烯作为亚家族V孤儿核受体（NR5A），肝受体同源物1（LRH-1）和类固醇生成因子-1（ SF-1）。使用基于荧光共振能量转移（FRET）的生化分析，化合物5a（GSK8470）被确定为LRH-1和SF-1的高亲和力配体。在肝细胞中，5a增加了LRH-1靶基因小异二聚体伴侣（SHP）的表达。在三个位置修饰的类似物的合成导致开发出在LRH-1和SF-1之间具有功能选择性的化合物。

  DOI：

  10.1021/jm060990k
• 作为产物：
  描述：

  三环己基硼烷 在 sodium hydroxide 、 正丁基锂 、 potassium tert-butylate 、 四丁基氟化铵 、 双氧水 、 碘 、 三氧化硫吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 (hept-1-en-6-yn-7-yl)cyclohexane
  参考文献：
  名称：

  Sequential Cyclization/Silylation of Enynes Catalyzed by an Organoyttrium Complex

  摘要：

  The organoyttrium complex Cp*2YCH3.THF (Cp* = C5Me5) has been shown to be an effective precatalyst for the selective sequential cyclization/silylation of 1,6- and 1,7-enynes.. The catalyst's ability to insert the alkyne in preference to the alkene in a regioselective manner, combined with the high diastereoselectivity of the insertion process, yields a product with only one stereochemistry about the exocyclic olefin. The reaction proceeds under extremely mild conditions with short reaction times. Cyclization of enynes functionalized in the allylic position affords silylated carbocycles with high diastereoselectivities and excellent yields.

  DOI：

  10.1021/ja971538g

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。
• 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.
• Identification of Small Molecule Agonists of the Orphan Nuclear Receptors Liver Receptor Homolog-1 and Steroidogenic Factor-1
  作者：Richard J. Whitby、Sally Dixon、Patrick R. Maloney、Philippe Delerive、Bryan J. Goodwin、Derek J. Parks、Timothy M. Willson

  DOI：10.1021/jm060990k

  日期：2006.11.1

  We report the identification of substituted cis-bicyclo[3.3.0]-oct-2-enes as small molecule agonists of subfamily V orphan nuclear receptors (NR5A), liver receptor homolog-1 (LRH-1) and steroidogenic factor-1 (SF-1). Using fluorescence resonance energy transfer (FRET)-based biochemical assays, compound 5a (GSK8470) was identified as a high-affinity ligand for LRH-1 and SF-1. In liver cells, 5a increased

  我们报告了取代的顺式-双环[3.3.0]-辛-2-烯作为亚家族V孤儿核受体（NR5A），肝受体同源物1（LRH-1）和类固醇生成因子-1（ SF-1）。使用基于荧光共振能量转移（FRET）的生化分析，化合物5a（GSK8470）被确定为LRH-1和SF-1的高亲和力配体。在肝细胞中，5a增加了LRH-1靶基因小异二聚体伴侣（SHP）的表达。在三个位置修饰的类似物的合成导致开发出在LRH-1和SF-1之间具有功能选择性的化合物。
• Sequential Cyclization/Silylation of Enynes Catalyzed by an Organoyttrium Complex
  作者：Gary A. Molander、William H. Retsch

  DOI：10.1021/ja971538g

  日期：1997.9.1

  The organoyttrium complex Cp*2YCH3.THF (Cp* = C5Me5) has been shown to be an effective precatalyst for the selective sequential cyclization/silylation of 1,6- and 1,7-enynes.. The catalyst's ability to insert the alkyne in preference to the alkene in a regioselective manner, combined with the high diastereoselectivity of the insertion process, yields a product with only one stereochemistry about the exocyclic olefin. The reaction proceeds under extremely mild conditions with short reaction times. Cyclization of enynes functionalized in the allylic position affords silylated carbocycles with high diastereoselectivities and excellent yields.