phenyl 2-phenylhexyl ketone | 1454-57-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: phenyl 2-phenylhexyl ketone
• 英文别名: 1,3-diphenyl-1-hepten-3-ol；1,3-Diphenylheptane-1-one；1,3-diphenyl-1-heptanone；(+/-)-1,3-Diphenyl-heptan-1-on；1,3-Diphenylheptan-1-on；1-Heptanone, 1,3-diphenyl-；1,3-diphenylheptan-1-one
• CAS: 1454-57-5
• 化学式: C₁₉H₂₂O
• 分子量: 266.383
• InChiKey: JARDRIGVVNPARG-UHFFFAOYSA-N

物化性质

• 熔点：
  55 °C
• 沸点：
  396.6±21.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  phenyl 2-phenylhexyl ketone 、 N,N-二甲基甲酰胺 在 甲酸 作用下， 生成 opt.-inakt. Dimethyl-(1.3-diphenyl-heptyl)-amin
  参考文献：
  名称：

  Lespagnol,A. et al., Bulletin de la Societe Chimique de France, 1964, p. 1507 - 1508

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(Benzyloxymethyl-tert-butyl-methyl-silanyl)-1,3-diphenyl-heptan-1-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 以73%的产率得到phenyl 2-phenylhexyl ketone
  参考文献：
  名称：

  A chiral (alkoxy)methyl-substituted silicon group as an auxiliary for the stereoselective cuprate addition to α,β-unsaturated ketones: synthesis of (−)-(R)-phenyl 2-phenylpropyl ketone

  摘要：

  The [(benzyloxy)methyl](tert-butyl)methylsilyl group was used as the chiral auxiliary to effect highly diastereoselective conjugate additions of organocuprates to enones. Thus, reaction of several R2CuLi with alpha-silylated alpha,beta-unsaturated ketones afforded the respective addition products with pi-face selectivities of up to 99%. Starting with an optically active substrate, enantiomerically enriched (-)-(R)-phenyl 2-phenylpropyl ketone was prepared with virtually no loss of chiral information in a reaction sequence involving cuprate addition, hydrolysis, and removal of the silicon group. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00134-1

文献信息

• Heterogeneous catalytic 1,4-addition of arylmagnesium compounds to chalcones
  作者：Kinga Juhász、Zoltán Hell

  DOI：10.1016/j.tetlet.2018.07.016

  日期：2018.8

  Copper(II) on a 4 Å molecular sieve support catalyses the chemoselective addition of alkyl- and arylmagnesium halides to chalcones. Only the 1,4-addition products were obtained in high yields.

  4Å分子筛载体上的铜（II）催化烷基和芳基卤化镁向查耳酮的化学选择性加成。仅以高收率获得了1，4-加成产物。
• Chiral Homoenolate Equivalents, V. Hydroxylakylation of Lithiated 3‐[( <i>S</i> )‐2‐(Methoxymethyl)pyrrolidino]‐1,3‐diphenylpropene – An Asymmetric Homoaldol Reaction
  作者：Hubertus Ahlbrecht、Andreas Kramer

  DOI：10.1002/cber.19961291004

  日期：1996.10

  hydroxyalkylation of lithiated 3-[(S)-2-(methoxymethyl)-pyrrolidino]-1,3-diphenylpropene (2) with aldehydes is completely regioselective giving homoaldol adducts in good yields. The simple diastereoselectivity is low with typical ratios ranging between 1:1 and 1:3 with the syn isomer predominating. The induced diastereoselectivity is much higher and is strongly solvent-dependent. The reaction predominantly

  锂化的3-[（（S）-2-（甲氧基甲基）-吡咯烷基] -1,3-二苯基丙烯（2）的羟烷基与醛的完全区域选择性，以高收率得到均醛醇加合物。简单的非对映选择性是低的典型比率1之间的范围内：1和1：3顺式异构体为主的。诱导的非对映选择性更高，并且强烈依赖溶剂。该反应主要根据金属固位机理在THF以及TBME中从烯丙基系统的si侧进行。通过使用较少溶剂化的TBME所获得的诱导的非对映选择性大大高于在强溶剂化THF中的诱导的非对映选择性，达到了高达97％ee的选择性。
• Tetraorganogallate Complexes in Organic Chemistry: Michael Addition to α,β-unsaturated Compounds
  作者：Ying Han、Yao-Zeng Huang、Lei Fang、Wen-Tian Tao

  DOI：10.1080/00397919908086045

  日期：1999.3

  Abstract Tetraorganogallate complexes, prepared in situ by addition of an organolithium reagent to a triorganogallium, reacted smoothly with α,β-unsaturated compounds to give Michael addition products in high yields, and mixed gallates display very high chemoselectivity in the transfer of one of their ligands.

  摘要 四有机镓酸盐配合物是通过将有机锂试剂加成到三有机镓中而原位制备的，它与 α,β-不饱和化合物顺利反应，以高产率得到迈克尔加成产物，并且混合镓酸盐在其配体之一的转移中显示出非常高的化学选择性。 .
• Enantioselektive 1,4-Additionen von metallorganischen Verbindungen an konjugierte Systeme im chiralen Medium DDB
  作者：Werner Langer、Dieter Seebach

  DOI：10.1002/hlca.19790620604

  日期：1979.9.19

  Enantioselective 1,4-additions of organometallic compounds to conjugated systems in the chiral medium DDB1

  在手性介质DDB 1中，将有机金属化合物对映选择性1,4-加成到共轭体系中
• Enantioselective Copper-Catalyzed 1,4-Addition ofGrignard Reagents to ?,?-Unsaturated Carbonyl Compounds
  作者：Maurus Spescha、Grety Rihs

  DOI：10.1002/hlca.19930760309

  日期：1993.5.12

  several reaction conditions. The chemical yields and regioselectivities for this reaction were, in all cases, larger than 90 and 98%, respectively, and independent of the experimental conditions. The enantioselectivity was strongly dependent on the reaction conditions and reached a maximum of 60%. Several other substrates were also tested in the above reaction. The X-ray crystal structure for [Cu(siig)(pp)]

  用以下Cu I化合物作为催化剂前体和1,2：5,6-di- O研究了对映选择性铜催化的格氏试剂向α，β-不饱和羰基化合物的1,4-加成反应-异亚丙基-3-硫代-α-D-呋喃葡萄糖（Hsiig）作为手性配体：CuI，碘代[双（二丁基硫醚）]铜（I），[Cu（siig）]，[Cu（siig）（pp）]（ pp ＝ 1，2-双）（二苯基膦基乙烯）和四[碘（三丁基膦）]铜（I）。在几个反应条件下测试了将BuMg卤化物添加到cyclohex-2-en-1-one中。在所有情况下，该反应的化学产率和区域选择性分别大于90％和98％，并且与实验条件无关。对映选择性在很大程度上取决于反应条件，最高达到60％。在上述反应中还测试了其他几种底物。[Cu（siig）（pp）]的X射线晶体结构通过X射线晶体学确定。