1-(2-hydroxy-phenyl)-hept-6-en-1-one | 526208-11-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-hydroxy-phenyl)-hept-6-en-1-one
• 英文别名: 1-(2-Hydroxyphenyl)hept-6-EN-1-one；1-(2-hydroxyphenyl)hept-6-en-1-one
• CAS: 526208-11-7
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: ZBBNBBIRJCOZIF-UHFFFAOYSA-N

物化性质

• 沸点：
  324.8±25.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-phenyl)-hept-6-en-1-one 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2-pent-4-enyl-benzofuran-3-one
  参考文献：
  名称：

  Unexpected Migration and Oxidative Cyclization of Substituted 2-Acetophenone Triflates under Basic Conditions:  Synthetic and Mechanistic Insights

  摘要：

  Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 degreesC. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions. Potential mechanistic pathways are evaluated.

  DOI：

  10.1021/jo0352023
• 作为产物：
  描述：

  6-庚烯酸 在 正丁基锂 、 三氯化硼 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.92h， 生成 1-(2-hydroxy-phenyl)-hept-6-en-1-one
  参考文献：
  名称：

  Unexpected Migration and Oxidative Cyclization of Substituted 2-Acetophenone Triflates under Basic Conditions:  Synthetic and Mechanistic Insights

  摘要：

  Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 degreesC. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions. Potential mechanistic pathways are evaluated.

  DOI：

  10.1021/jo0352023

文献信息

• Double-Chelation-Assisted Rh-Catalyzed Intermolecular Hydroacylation between Salicylaldehydes and 1,4-Penta- or 1,5-Hexadienes
  作者：Masanori Imai、Masakazu Tanaka、Keitaro Tanaka、Yoichiro Yamamoto、Naoko Imai-Ogata、Masato Shimowatari、Shinji Nagumo、Norio Kawahara、Hiroshi Suemune

  DOI：10.1021/jo035395u

  日期：2004.2.1

  Intermolecular hydroacylation between salicylaldehydes 1, 26−40 and 1,4-penta- or 1,5-hexadienes 4−13 by Rh-catalyst proceeded under mild reaction conditions to give a mixture of iso- and normal-hydroacylated products 14−25, 41−55, and 57−60. In the hydroacylation reaction, chelation of both salicylaldehyde and diene to the Rh-complex plays a crucial role. The ratio of iso- and normal-hydroacylated

  水杨醛之间的分子间加氢酰化1，26 - 40和1,4-五-或1,5-己二烯4 - 13由Rh的催化剂在温和的反应条件下进行，得到的混合物异-和正常-hydroacylated产品14 - 25，41 - 55，和57 - 60。在加氢酰化反应中，水杨醛和二烯与Rh络合物的螯合起关键作用。等值线与正常值之比可以通过添加水杨酸或胺来调节-氢酰化产物。在氘标记水杨醛实验的基础上，研究了各种Rh络合物，溶剂和添加剂的作用，并提出了催化循环的合理机理。
• Double-Chelation-Assisted Rh-Catalyzed Intermolecular Hydroacylation
  作者：Masakazu Tanaka、Masanori Imai、Yoichiro Yamamoto、Keitaro Tanaka、Masato Shimowatari、Shinji Nagumo、Norio Kawahara、Hiroshi Suemune

  DOI：10.1021/ol034343o

  日期：2003.4.1

  [reaction: see text] Rh-Catalyzed intermolecular hydroacylation between salicylaldehydes and 1,5-hexadienes proceeded under remarkably mild reaction conditions to afford a mixture of iso- and normal-hydroacylated products in good yields. The experiments using deuterated salicylaldehyde-d revealed that "double chelation" of salicylaldehyde and 1,5-hexadiene to Rh-complex played vital roles in the catalytic

  [反应：见正文]水杨醛和1,5-己二烯之间的Rh催化的分子间加氢酰化反应在非常温和的反应条件下进行，以高收率得到了异-和正-加氢酰化产物的混合物。使用氘代水杨醛-d进行的实验表明，水杨醛和1,5-己二烯与Rh复合物的“双重螯合”在分子间加氢酰化的催化循环中起着至关重要的作用。
• Nitrile-Promoted Rh-Catalyzed Intermolecular Hydroacylation of Olefins with Salicylaldehyde
  作者：Masanori Imai、Masakazu Tanaka、Shinji Nagumo、Norio Kawahara、Hiroshi Suemune

  DOI：10.1021/jo062501u

  日期：2007.3.1

  Rh-catalyzed intermolecular hydroacylation between salicylaldehyde and alkenylnitriles proceeded at room temperature to preferentially give normal-hydroacylated products. Addition of CH3CN and NaOAc accelerated the Rh-catalyzed hydroacylation of monoolefins to exclusively produce the normal-hydroacylated products under mild reaction conditions. Plausible mechanisms for the regioselections are also

  水杨醛和链烯腈之间的Rh催化的分子间加氢酰化反应在室温下进行，优先得到正加氢酰化的产物。在温和的反应条件下，CH 3 CN和NaOAc的加入加速了Rh催化的单烯烃加氢酰化反应，从而独家生产出正常的加氢酰化产物。还描述了可能的区域选择机制。
• Nickel-Catalyzed Directed Cross-Electrophile Coupling of Phenolic Esters with Alkyl Bromides
  作者：Feiyan Yang、Decai Ding、Chuan Wang

  DOI：10.1021/acs.orglett.0c03342

  日期：2020.12.4

  electrophilic acyl source in the reaction with diverse primary and secondary unactivated alkyl bromides. The cleavage of the relatively inert C–O bond is facilitated by the neighboring coordinating hydroxyl or sulfonamide moiety. By circumventing the use of pregenerated organometallics, this method allows efficient preparation of a variety of o-hydroxyl and tosyl-protected o-amino aryl ketones with high compatibility

  在本文中，我们证明了在各种伯和仲未活化烷基溴的反应中，成功使用了强健的酚酯作为亲电子酰基源。相邻的羟基或磺酰胺部分可促进相对惰性的C-O键的裂解。通过避免使用预生成的有机金属，该方法可以有效地制备具有高相容性和广泛功能的各种邻羟基和甲苯磺酰基保护的邻氨基芳基酮。
• Unexpected Migration and Oxidative Cyclization of Substituted 2-Acetophenone Triflates under Basic Conditions:  Synthetic and Mechanistic Insights
  作者：Jotham W. Coe、Krista E. Bianco、Brian P. Boscoe、Paige R. Brooks、Eric D. Cox、Michael G. Vetelino

  DOI：10.1021/jo0352023

  日期：2003.12.1

  Oxidative ring closure of alkyl-substituted 2-hydroxyacetophenone trifluoromethanesulfonate esters (triflates) occurs upon exposure to base in anaerobic DMF at 20-90 degreesC. Alkyl substitution is required for ring closure. A migrated enol triflate product forms at lower temperature in high yield via migration of the trifluoromethanesulfonate in the unsubstituted and monoalkyl-substituted cases. The alkyl-substituted enol triflates also enter into the benzofuran-3-one ring-forming process under thermal cyclization conditions. Potential mechanistic pathways are evaluated.