1-(Bicyclo<2.2.1>hept-5-en-2-yl)-2-propen-1-on | 100234-78-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(Bicyclo<2.2.1>hept-5-en-2-yl)-2-propen-1-on
• 英文别名: 1-(bicyclo[2.2.1]hept-5-en-2-yl)prop-2-en-1-one；Bicyclo[2.2.1]hept-2-ene-5-yl, vinyl ketone；1-(2-bicyclo[2.2.1]hept-5-enyl)prop-2-en-1-one
• CAS: 100234-78-4
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: OWDVHQGGVUTHMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  85-100 °C(Press: 10 Torr)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(Bicyclo<2.2.1>hept-5-en-2-yl)-2-propen-1-on 在 3-苄基羟乙基甲基噻唑氯化锂 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 生成 2,15-Dimethyl-4,7,10,13-hexadecantetron
  参考文献：
  名称：

  Stetter, Hermann; Jansen, Bernhard, Chemische Berichte, 1985, vol. 118, # 12, p. 4877 - 4883

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(Bicyclo<2.2.1>hept-5-en-2-yl)-3-chlor-1-propanon 以91%的产率得到
  参考文献：
  名称：

  STETTER, H.;JANSEN, B., CHEM. BER., 1985, 118, N 12, 4877-4883

  摘要：

  DOI：

文献信息

• Ruthenium<i>Lewis</i>Acid-Catalyzed Asymmetric<i>Diels-Alder</i>Reactions: Reverse-Face Selectivity for<i>α</i>,<i>β</i>-Unsaturated Aldehydes and Ketones
  作者：Sirinporn Thamapipol、Bettina Ludwig、Céline Besnard、Christophe Saudan、E. Peter Kündig

  DOI：10.1002/hlca.201600139

  日期：2016.10

  Acrolein, methacrolein, methyl vinyl ketone, ethyl vinyl ketone, 3‐methyl‐3‐en‐2‐one, and divinyl ketone were coordinated to a cationic cyclopentadienyl ruthenium(II) Lewis acid incorporating the electron‐poor bidentate BIPHOP–F ligand. Analysis by NOESY and ROESY NMR techniques allowed the determination of conformations of enals and enones present in solution in CD2Cl2. The results were compared to

  丙烯醛，甲基丙烯醛，甲基乙烯基酮，乙基乙烯基酮，3-甲基-3-烯-2-酮和二乙烯基酮与阳离子环戊二烯基钌（II）路易斯酸配位，并掺入了贫电子的双齿BIPHOP-F配体。通过NOESY和ROESY NMR技术进行分析，可以测定CD 2 Cl 2中溶液中存在的烯醛和烯酮的构象。将结果与固态结构和催化不对称Diels-Alder与环戊二烯的面部选择性进行了比较。四个Ru-enal和Ru-enone配合物的X-射线结构表明，α，β-不饱和C = O化合物采用反s-反构象。在解决方案中，Enals假定同时存在反反构和反顺构构。烯酮配合物中还存在另一种构象syn-s-trans。环加成反应中的对映体选择性对于烯醛和烯酮是不同的。反应产物表明烯类只在反-s-反式构象中反应，而对于烯酮，主要产物是syn-s-反式构象。顺式构象的烯烃，尽管存在于溶液中，却被屏蔽并且不能进行环加成反应。一个SYN-S反在庞大的6
• Inhibitors of cholesterol biosynthesis. 1. trans-6-(2-Pyrrol-1-ylethyl)-4-hydroxypyran-2-ones, a novel series of HMG-CoA reductase inhibitors. 1. Effects of structural modifications at the 2- and 5-positions of the pyrrole nucleus
  作者：Bruce D. Roth、D. F. Ortwine、M. L. Hoefle、C. D. Stratton、D. R. Sliskovic、M. W. Wilson、R. S. Newton

  DOI：10.1021/jm00163a005

  日期：1990.1

  A novel series of trans-6-(2-pyrrol-1-ylethyl)-4-hydroxypyran-2-ones and their dihydroxy acid derivatives were prepared and evaluated for their ability to inhibit the enzyme HMG-CoA reductase in vitro. A systematic study of substitution at the 2- and 5-positions of the pyrrole ring revealed that optimum potency was realized with the 2-(4-fluorophenyl)-5-isopropyl derivative 8x, which possessed 30% of the in vitro activity of the potent fungal metabolite compactin (I). A molecular modeling analysis led to the description of a pharmacophore model characterized by (A) length limits of 5.9 and 3.3 A for the 2- and 5-substituents, respectively, as well as an overall width limit of 10.6 A across the pyrrole ring from the 2- to the 5-substituent and (B) an orientation of the ethyl(ene) bridge to the 4-hydroxypyran-2-one ring nearly perpendicular to the planes of the parent pyrrole, hexahydronaphthalene, and phenyl rings of the structures examined (Figure 3, theta = 80-110 degrees). Attempts to more closely mimic compactin's polar isobutyric ester side chain with the synthesis of 2-phenylpyrroles containing polar phenyl substituents resulted in analogues with equal or slightly reduced potencies when compared to the 2-[(unsubstituted or 4-fluoro)phenyl]pyrroles, supporting the hypothesis that inhibitory potency is relatively insensitive to side-chain polarity or charge distribution in this area.
• Stetter, Hermann; Jansen, Bernhard, Chemische Berichte, 1985, vol. 118, # 12, p. 4877 - 4883
  作者：Stetter, Hermann、Jansen, Bernhard

  DOI：——

  日期：——
• STETTER, H.;JANSEN, B., CHEM. BER., 1985, 118, N 12, 4877-4883
  作者：STETTER, H.、JANSEN, B.

  DOI：——

  日期：——