(E)-5-(benzyloxy)-1-phenylpent-2-en-1-one | 92074-34-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-5-(benzyloxy)-1-phenylpent-2-en-1-one
• 英文别名: (E)-1-phenyl-5-phenylmethoxypent-2-en-1-one
• CAS: 92074-34-5
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: AVUTTWORUVKACS-NTUHNPAUSA-N

物化性质

• 沸点：
  404.1±45.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-5-(benzyloxy)-1-phenylpent-2-en-1-one 在 正丁基锂 、 4-(tert-Butyl)-2-(quinolin-2-yl)-4,5-dihydrooxazole 、 C₂H₄Br₂CoO₂ 、 sodium hydride 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基乙酰胺 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 34.5h， 生成 (E)-5-(2-(benzyloxy)ethyl)-3-(4-methoxybenzylidene)-2,3,4,5-tetrahydro-1,1'-biphenyl
  参考文献：
  名称：

  乙烯基环丙烷和亚乙烯基的催化 [5 + 1]-环加成

  摘要：

  使用 Diels-Alder 反应（邻位规则）获得具有 1,3（元）取代模式的多取代环己烯具有挑战性。在这里，我们报告了乙烯基环丙烷和亚乙烯基之间的钴催化还原性 [5 + 1]-环加成反应，以提供具有全金属关系的亚甲基环己烯。使用 Zn 作为化学计量还原剂从 1,1-二氯烯烃生成亚乙烯基等价物。实验观察与涉及由亚乙烯基钴和乙烯基环丙烷之间的[2+2]-环加成形成的环丁烷钴的机制一致。

  DOI：

  10.1021/jacs.0c00356
• 作为产物：
  描述：

  2-溴苯乙酮 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 48.0h， 生成 (E)-5-(benzyloxy)-1-phenylpent-2-en-1-one
  参考文献：
  名称：

  Catalytic Cyclooligomerization of Enones with Three Methylene Equivalents

  摘要：

  Cyclic structures are highly represented in organic molecules, motivating a wealth of catalytic methods targeting their synthesis. Among the various ring-forming processes, cyclooligomerization reactions possess several attractive features but require addressing a unique challenge associated with controlling ring-size selectivity. Here we describe the catalytic reductive cocyclooligomerization of an enone and three carbene equivalents to generate a cyclopentane, a process that constitutes a formal [2 + 1 + 1 + 1]-cycloaddition. The reaction is promoted by a (quinox)Ni catalyst and uses CH2Cl2/Zn as the C-1 component. Mechanistic studies are consistent with a metallacycle-based pathway, featuring sequential migratory insertions of multiple carbene equivalents to yield cycloalkanes larger than cyclopropanes.

  DOI：

  10.1021/jacs.8b08296

文献信息

• Phase-Transfer-Catalyzed Asymmetric Synthesis of Chiral<i>N</i>-Substituted Pyr­azoles by Aza-Michael Reaction
  作者：Su-Jeong Lee、Ju-Yeon Bae、Chang-Woo Cho

  DOI：10.1002/ejoc.201500940

  日期：2015.9

  cinchona-based phase-transfer-catalyzed asymmetric aza-Michael reaction of pyrazole with various α,β-unsaturated ketones has been developed for the preparation of chiral N-substituted pyrazoles. This reaction provided the desired products in good yields (up to 99 %) with excellent enantioselectivities (87–94 % ee). In addition, the reaction of 3-methyl-1H-pyrazole, an unsymmetrically substituted pyrazole

  已经开发了一种有效的基于金鸡纳的相转移催化的吡唑与各种 α,β-不饱和酮的不对称氮杂-迈克尔反应，用于制备手性 N-取代吡唑。该反应以良好的收率（高达 99%）提供了所需的产物，并具有出色的对映选择性（87-94% ee）。此外，3-甲基-1H-吡唑，一种不对称取代的吡唑，用α,β-不饱和酮处理，得到相应的手性N-取代吡唑，产率高（高达99%），具有优异的对映选择性（ 90–92 % ee) 和高达 9:1 的区域异构比率。
• Regioselective stannylmetalation of acetylenes in the presence of transition-metal catalyst
  作者：Jun-ichi Hibino、Seijiro Matsubara、Yoshitomi Morizawa、Koichiro Oshima、Hitosi Nozaki

  DOI：10.1016/s0040-4039(01)81185-0

  日期：1984.1

  The reaction of terminal acetylenes with Bu3SnMgMe, Bu3SnA1Et2, or (Bu3Sn)2Zn in the presence of various transition-metal catalysts provides vinylstannanes in good yields. Whereas copper catalysed stannylmagnesation of 4-benzyloxy-1-butyne gives (E)-4-benzyloxy-1-tributylstannyl-1-butene exclusively, palladium catalysed stannylzincation affords 4-benzyloxy-2-tributylstannyl-1-butene preferentially

  在各种过渡金属催化剂存在下，末端乙炔与Bu 3 SnMgMe，Bu 3 SnA1Et 2或（Bu 3 Sn）2 Zn的反应提供了高产率的乙烯基锡烷。铜催化4-苄氧基-1-丁炔的苯乙烯基甲酸酯化仅生成（E）-4-苄氧基-1-三丁基锡烷基-1-丁烯，而钯催化的苯乙烯基锌酸酯优先提供4-苄氧基-2-三丁基锡烷基-1-丁烯。
• HIBINO, JUN-ICHI;MATSUBARA, SEIJIRO;MORIZAWA, YOSHITOMI;OSHIMA, KOICHIRO;+, TETRAHEDRON LETT., 1984, 25, N 20, 2151-2154
  作者：HIBINO, JUN-ICHI、MATSUBARA, SEIJIRO、MORIZAWA, YOSHITOMI、OSHIMA, KOICHIRO、+

  DOI：——

  日期：——
• Catalytic Cyclooligomerization of Enones with Three Methylene Equivalents
  作者：Conner M. Farley、You-Yun Zhou、Nishit Banka、Christopher Uyeda

  DOI：10.1021/jacs.8b08296

  日期：2018.10.10

  Cyclic structures are highly represented in organic molecules, motivating a wealth of catalytic methods targeting their synthesis. Among the various ring-forming processes, cyclooligomerization reactions possess several attractive features but require addressing a unique challenge associated with controlling ring-size selectivity. Here we describe the catalytic reductive cocyclooligomerization of an enone and three carbene equivalents to generate a cyclopentane, a process that constitutes a formal [2 + 1 + 1 + 1]-cycloaddition. The reaction is promoted by a (quinox)Ni catalyst and uses CH2Cl2/Zn as the C-1 component. Mechanistic studies are consistent with a metallacycle-based pathway, featuring sequential migratory insertions of multiple carbene equivalents to yield cycloalkanes larger than cyclopropanes.
• Catalytic [5 + 1]-Cycloadditions of Vinylcyclopropanes and Vinylidenes
  作者：Conner M. Farley、Kohei Sasakura、You-Yun Zhou、Vibha V. Kanale、Christopher Uyeda

  DOI：10.1021/jacs.0c00356

  日期：2020.3.11

  1]-cycloaddition between a vinylcyclopropane and a vinylidene to provide methylenecyclohexenes bearing all-meta relationships. Vinylidene equivalents are generated from 1,1-dichloroalkenes using Zn as a stoichiometric reductant. Experimental observations are consistent with a mechanism involving a cobaltacyclobutane formed from a [2 + 2]-cycloaddition between a cobalt vinylidene and a vinylcyclopropane.

  使用 Diels-Alder 反应（邻位规则）获得具有 1,3（元）取代模式的多取代环己烯具有挑战性。在这里，我们报告了乙烯基环丙烷和亚乙烯基之间的钴催化还原性 [5 + 1]-环加成反应，以提供具有全金属关系的亚甲基环己烯。使用 Zn 作为化学计量还原剂从 1,1-二氯烯烃生成亚乙烯基等价物。实验观察与涉及由亚乙烯基钴和乙烯基环丙烷之间的[2+2]-环加成形成的环丁烷钴的机制一致。