2-ethyl-4-phenyl-but-2-enal | 672937-22-3

• 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: 2-ethyl-4-phenyl-but-2-enal
• 英文别名: 2-Ethyl-4-phenylbut-2-enal；2-ethyl-4-phenylbut-2-enal
• CAS: 672937-22-3
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: WPYXOOQGKRKIPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-ethyl-4-phenyl-but-2-enal 在 二异丁基氢化铝 作用下， 以 甲苯 、 苯 为溶剂， 反应 20.25h， 生成 2,4-diethyl-6-phenyl-hexa-2,5-dien-1-ol
  参考文献：
  名称：

  Non-canonical regioisomerizations and a ‘Diels–Alderase’ are likely essential in the biosynthesis of Spiculoic acid A

  摘要：

  The regiochemistry of dehydration and cyclization steps of the linear biosynthetic precursor of the polyketide natural product Spiculoic acid A (1) were examined. Herein we describe the synthesis of polyene-containing aldehyde 21, a counterpart to the metabolite's putative polyketide intermediate and demonstrate its inability to undergo facile IMDA chemistry. These results suggest the involvement of a non-canonical regioisomerization in the biosynthesis of 1, and that the IMDA reaction is likely enzyme-catalyzed. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.052
• 作为产物：
  描述：

  2-ethyl-4-phenyl-but-2-enoic acid ethyl ester 在 二异丁基氢化铝 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 1.41h， 生成 2-ethyl-4-phenyl-but-2-enal
  参考文献：
  名称：

  Non-canonical regioisomerizations and a ‘Diels–Alderase’ are likely essential in the biosynthesis of Spiculoic acid A

  摘要：

  The regiochemistry of dehydration and cyclization steps of the linear biosynthetic precursor of the polyketide natural product Spiculoic acid A (1) were examined. Herein we describe the synthesis of polyene-containing aldehyde 21, a counterpart to the metabolite's putative polyketide intermediate and demonstrate its inability to undergo facile IMDA chemistry. These results suggest the involvement of a non-canonical regioisomerization in the biosynthesis of 1, and that the IMDA reaction is likely enzyme-catalyzed. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.052

文献信息

• Improvement of primary-amine-catalyzed asymmetric α-benzoyloxylation of α-branched enals by a synergistic effect of water and sulfonic acids
  作者：Satoru Arimitsu、Emi Gima

  DOI：10.1016/j.tetlet.2020.152032

  日期：2020.6

  The asymmetric α-benzoyloxylation of α-branched enals developed by List was reinvestigated to further improve its reaction efficiency and enantioselectivity. After optimizing the reaction conditions, the synergistic effect of water and sulfonic acid in DMSO was revealed. The reaction efficiency was improved reducing the reaction time, and moderate enantioselectivities (up to 81% ee) with excellent

  重新研究了List所开发的α-支链烯键的不对称α-苯甲酰氧基化反应，以进一步提高其反应效率和对映选择性。优化反应条件后，揭示了水和磺酸在DMSO中的协同作用。缩短了反应时间，提高了反应效率，并实现了中等的对映选择性（最高81％ee）和极佳的E选择性（E / Z  => 20/1）。尽管区域选择性不高（α/γ= 1 / 1–6 / 1），但α-区域异构体2a已成功用于合成由含氧季铵碳和两个烯丙基单元组成的高立体控制化合物（E / Z  = 20 / 1，20/1）。
• Non-canonical regioisomerizations and a ‘Diels–Alderase’ are likely essential in the biosynthesis of Spiculoic acid A
  作者：Atahualpa Pinto、Christopher N. Boddy

  DOI：10.1016/j.bmcl.2012.06.052

  日期：2012.8

  The regiochemistry of dehydration and cyclization steps of the linear biosynthetic precursor of the polyketide natural product Spiculoic acid A (1) were examined. Herein we describe the synthesis of polyene-containing aldehyde 21, a counterpart to the metabolite's putative polyketide intermediate and demonstrate its inability to undergo facile IMDA chemistry. These results suggest the involvement of a non-canonical regioisomerization in the biosynthesis of 1, and that the IMDA reaction is likely enzyme-catalyzed. (c) 2012 Elsevier Ltd. All rights reserved.