3-(4-Methoxyphenyl)-3-methylcyclobutan-1-one | 401895-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-Methoxyphenyl)-3-methylcyclobutan-1-one
• CAS: 401895-06-5
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: CMXBIZDEPOIKSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  299.8±40.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  3-(4-Methoxyphenyl)-3-methylcyclobutan-1-one 在 4,5-dihydroimidazol-2-ylidene-Ru sodium tetrahydroborate 、 potassium tert-butylate 作用下， 以 吡啶 、 甲醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 48.0h， 生成 1-methoxy-4-(3-methylhexa-1,5-dien-3-yl)benzene
  参考文献：
  名称：

  Employment of a cyclobutene ring-opening metathesis reaction towards a concise synthesis of (±)-sporochnol A

  摘要：

  A concise formal synthesis of (+/-)-sporochnol A 1, a naturally occurring feeding deterrent towards herbivorous fish, is described. The target compound was prepared by the employment of a Ru-catalysed cyclobutene ring-opening metathesis reaction with gaseous ethylene followed by a site selective hydroboration reaction as the key steps. The optimisation of the metathesis process regarding the Ru-catalyst and reaction conditions is also delineated. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02007-x
• 作为产物：
  描述：

  在 氯化铵 、 锌 作用下， 以 甲醇 为溶剂， 生成 3-(4-Methoxyphenyl)-3-methylcyclobutan-1-one
  参考文献：
  名称：

  Employment of a cyclobutene ring-opening metathesis reaction towards a concise synthesis of (±)-sporochnol A

  摘要：

  A concise formal synthesis of (+/-)-sporochnol A 1, a naturally occurring feeding deterrent towards herbivorous fish, is described. The target compound was prepared by the employment of a Ru-catalysed cyclobutene ring-opening metathesis reaction with gaseous ethylene followed by a site selective hydroboration reaction as the key steps. The optimisation of the metathesis process regarding the Ru-catalyst and reaction conditions is also delineated. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02007-x

文献信息

• Wacker Oxidation of Methylenecyclobutanes: Scope and Selectivity in an Unusual Setting
  作者：Jan Sietmann、Marius Tenberge、Johannes M. Wahl

  DOI：10.1002/anie.202215381

  日期：2023.2.6

  Methylenecyclobutanes undergo Wacker oxidation towards cyclopentanones under mild reaction conditions. A semi-pinacol-type rearrangement is proposed to be responsible for the intermediary 1,2-shift, which not only explains the formation of the products, but also rationalizes the reaction outcomes in terms of site-, regio- and enantioselectivity.

  亚甲基环丁烷在温和的反应条件下经过瓦克氧化生成环戊酮。提出半频哪醇型重排负责中间 1,2-转移，这不仅解释了产物的形成，而且还使反应结果在位点、区域和对映选择性方面合理化。
• Palladium-Catalyzed Skeletal Rearrangement of Cyclobutanones via C–H and C–C Bond Cleavage
  作者：Yusuke Ano、Daichi Takahashi、Yuki Yamada、Naoto Chatani

  DOI：10.1021/acscatal.2c06389

  日期：2023.2.17

  The palladium-catalyzed skeletal rearrangement of 3-arylcyclobutanones into 1-indanones is reported. A Pd(0)/IMes catalyst allows for the cleavage of C(carbonyl)–C(sp3) and C(sp2)–H bonds to result in the skeletal rearrangement, and neither an extra reactive functional group nor a directing group is required to promote the reaction. Deuterium-labeling experiments indicate that the C–C bond is initially

  报道了钯催化的 3-芳基环丁酮骨架重排为 1-茚满酮。Pd(0)/IMes 催化剂允许裂解 C(carbonyl)–C(sp 3 ) 和 C(sp 2 )–H 键以导致骨架重排，并且既没有额外的反应性官能团也没有导向基团需要促进反应。氘标记实验表明 C-C 键最初被激活，随后的 C-H 激活参与决速步骤。
• Chemoselective Strain Release of Bicyclo[1.1.1]pent-1-yl Alcohols
  作者：Songjie Yu、Yue Ma、Yinan Ai

  DOI：10.1055/a-1992-6707

  日期：2023.3

  The chemoselective C–C bond cleavage of bicyclo[1.1.1]pent-1-yl alcohols (BCP-OHs) was examined. Highly ring-strained BCP-OHs were found to be particularly reactive, delivering cyclobutanone derivatives through a base-mediated single C–C bond cleavage or α,β-unsaturated ketones by palladium-catalyzed dual C–C bond cleavage.

  检查了双环[1.1.1]戊-1-醇 (BCP-OH) 的化学选择性 C-C 键裂解。发现高度环应变的 BCP-OH 具有特别的反应性，通过碱介导的单 C-C 键裂解产生环丁酮衍生物，或通过钯催化的双 C-C 键裂解产生 α,β-不饱和酮。