8,9-epoxy-1-phenyl-1-nonanone | 120568-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8,9-epoxy-1-phenyl-1-nonanone
• 英文别名: 7-(oxiran-2-yl)-1-phenylheptan-1-one
• CAS: 120568-23-2
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: ZHQJZJUWXGPMRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-溴-7,8-环氧丁烷 、 苯甲酰氯 在 copper(l) iodide 、 lithium dihydronaphthylide radical 、 三苯基膦 作用下， 生成 8,9-epoxy-1-phenyl-1-nonanone
  参考文献：
  名称：

  利用高反应性铜制备的新型有机铜试剂

  摘要：

  通过碘化亚铜（I）/三烷基膦配合物的萘锂制备了高反应性的铜溶液。这些活化的铜溶液将在非常温和的条件下与有机卤化物反应，形成稳定的有机铜试剂。重要的是，有机铜试剂可以包含大量的官能团，例如酯，腈，氯，环氧基和酮基。这些官能化的有机铜物质经历许多其他有机铜物质典型的反应。已经成功实现了分子间的1,4-加成，环氧化物开放反应以及与酰氯的酮形成。另外，该方法已经应用于分子内环氧化物裂解反应。连接链长度，取代方式，反应溶剂，

  DOI：

  10.1016/0040-4020(89)80072-9

文献信息

• Direct formation of functionalized ketones via the coupling of functionalized organocopper reagents with acid chlorides
  作者：Richard M. Wehmeyer、Reuben D. Rieke

  DOI：10.1016/s0040-4039(00)80534-1

  日期：1988.1

  reactive copper solutions have been prepared by the lithium naphthalide reduction of a copper(I) iodide/triphenyl-phosphine complex. These copper solutions react rapidly with functionalized alkyl halides to give organocopper reagents which have been effectively trapped with acid chlorides giving functionalized ketones in good yields. Ester, nitrile, chloride, remote epoxide, and, to some degree, ketone groups

  通过将碘化亚铜（I）/三苯基-膦配合物进行萘锂的还原，已经制备了高反应性的铜溶液。这些铜溶液与官能化的烷基卤化物迅速反应，生成有机铜试剂，有机铜试剂已被酰基氯有效地捕集，从而以良好的收率得到官能化的酮。这种方法可以耐受酯，腈，氯，远端环氧化物以及一定程度上的酮基。
• Direct formation and reaction of thienyl-based organocopper reagents
  作者：Reuben D. Rieke、Walter R. Klein、Tse Chong Wu

  DOI：10.1021/jo00061a024

  日期：1993.4

  The preparation of a highly reactive zerovalent copper complex by the direct reduction of lithium (2-thienylcyano)cuprate with preformed lithium naphthalenide is described. This active copper species oxidatively adds to carbon-halogen bonds to form organocopper reagents. The ability to directly form the organocopper reagent from organic halides and active copper allows for the incorporation of a wide variety of functionalities to be present in the organic halides and the organocopper reagents. Significantly, this formulation of active copper was able to oxidatively add to allyl chlorides and acetates at low temperatures to allow the direct formation of allylic organocopper reagents without Wurtz-type homocoupling. These functionalized organocopper compounds are able to undergo a variety of reactions, such as cross-coupling with acid chlorides, 1,4-conjugate addition with alpha,beta-unsaturated carbonyl compounds, and intermolecular and intramolecular epoxide-opening reactions. Subsequently, this copper species avoids the use of phosphine ligands affording the product isolation much more convenient than with phosphine-based organocopper reagents.
• RIEKE, REUBEN D.;WEHMEYER, RICHARD M.;WU, TSE-CHONG;EBERT, GREG W., TETRAHEDRON, 45,(1989) N, C. 443-454
  作者：RIEKE, REUBEN D.、WEHMEYER, RICHARD M.、WU, TSE-CHONG、EBERT, GREG W.

  DOI：——

  日期：——
• WEHMEYER, RICHARD M.;RIEKE, REUBEN D., TETRAHEDRON LETT., 29,(1988) N 36, C. 4513-4516
  作者：WEHMEYER, RICHARD M.、RIEKE, REUBEN D.

  DOI：——

  日期：——