piperonylidenecyclopropane | 118150-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: piperonylidenecyclopropane
• 英文别名: 5-(Cyclopropylidenemethyl)-1,3-benzodioxole
• CAS: 118150-02-0
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: KNPDWPOINCEDEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  piperonylidenecyclopropane 在 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 生成 1-(Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-cyclopropanol
  参考文献：
  名称：

  Asymmetric dihydroxylations of aromatic cyclopropylidenes

  摘要：

  A number of aromatic cyclopropylidenes have been converted to diols using the Sharpless asymmetric dihydroxylation (AD) procedure. The enantiomeric ratios were determined by chiral phase HPLC by comparison with their racemates. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01153-3
• 作为产物：
  描述：

  胡椒醛 、 溴化环丙基三苯鏻 在 三(3,6-二氧杂庚基)胺 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到piperonylidenecyclopropane
  参考文献：
  名称：

  An efficient method for the preparation of alkylidenecyclopropanes

  摘要：

  DOI：

  10.1016/s0040-4039(00)86104-3

文献信息

• Catalyst-controlled selective borocarbonylation of benzylidenecyclopropanes: regiodivergent synthesis of γ-vinylboryl ketones and β-cyclopropylboryl ketones
  作者：Fu-Peng Wu、Xiao-Feng Wu

  DOI：10.1039/d2sc00840h

  日期：——

  Various γ-vinylboryl ketones and β-cyclopropylboryl ketones were produced in moderate to good yields with excellent regioselectivity from the same substrates. The choice of the catalyst is key for the regioselectivity control: γ-vinylboryl ketones were produced selectively with IPrCuCl and Pd(dppp)Cl2 as the catalytic system, while the corresponding β-cyclopropylboryl ketones were obtained in high

  区域选择性催化多功能化反应能够从相同的前体快速合成络合产物。在本次交流中，我们提出了一种用芳基碘化物对苯亚甲基环丙烷进行区域发散硼羰基化的方法。各种γ-乙烯基硼基酮和β-环丙基硼基酮以中等至良好的产率从相同的底物产生，具有优异的区域选择性。催化剂的选择是区域选择性控制的关键：以 IPrCuCl 和 Pd(dppp)Cl 2为催化体系选择性制备 γ-乙烯基硼基酮，而以 Cu(dppp) 为催化体系获得了高区域选择性的 β-环丙基硼基酮Cl，[Pd( η 3 -肉桂基)Cl] 2和黄磷作为催化体系。此外，γ-乙烯基硼基酮和β-环丙基硼基酮成功地转化为其他几种增值产品。
• Rhodium‐Catalyzed Chemo‐, Regio‐ and Enantioselective Hydroformylation of Cyclopropyl‐Functionalized Trisubstituted Alkenes
  作者：Shuailong Li、Dequan Zhang、Runtong Zhang、Shao‐Tao Bai、Xumu Zhang

  DOI：10.1002/anie.202206577

  日期：2022.8.15

  ed highly chemo-, regio- and enantioselective hydroformylation of cyclopropyl-functionalized trisubstituted alkenes to afford high-value chiral cyclopropyl entities is reported. Insights into this transformation were established by control, deuteroformylation, and gram-scale reactions (TON up to 1500). Versatile follow-up transformations to the corresponding alcohol, acid, esters and nitrile were also

  报道了第一个铑-二膦催化的环丙基官能化三取代烯烃的高度化学、区域和对映选择性加氢甲酰化，以提供高价值的手性环丙基实体。通过对照、去甲酰化和克级反应（TON 高达 1500）建立了对这种转化的深入了解。还展示了对相应醇、酸、酯和腈的多种后续转化。
• Copper-catalyzed hydroaminocarbonylation of benzylidenecyclopropanes: synthesis of γ,δ-unsaturated amides
  作者：Hui-Qing Geng、Xiao-Feng Wu

  DOI：10.1039/d2cc02301f

  日期：——

  benzylidenecyclopropanes under relatively mild conditions. A series of γ,δ-unsaturated amides with a broad range of functional groups were obtained in moderate to good yields. Both dialkyl-substituted and monoalkyl-substituted hydroxylamine derivatives can be applied in this transformation to give the corresponding tertiary and secondary amides successfully.

  在此，我们开发了在相对温和的条件下铜催化的亚苄基环丙烷的氢氨基羰基化反应。以中等至良好的收率获得了一系列具有广泛官能团的γ,δ-不饱和酰胺。二烷基取代和单烷基取代的羟胺衍生物均可用于该转化，从而成功地得到相应的叔酰胺和仲酰胺。
• Photoredox-neutral ring-opening pyridylation of cyclic oximes via phosphoranyl radical-mediated N O/C C bond cleavages and sequential radical-radical coupling
  作者：Ting Zou、Yishu He、Rui Liu、Yihao Zhang、Siping Wei、Ji Lu、Jun Wang、Lin Wang、Qiang Fu、Dong Yi

  DOI：10.1016/j.cclet.2022.107822

  日期：2023.5

  A novel photoredox-neutral ring-opening pyridylation of non-prefunctionalized cyclic oximes has been accomplished through phosphoranyl radical-mediated NO/CC bond cleavages followed by radical-radical coupling. This mild acid-, base-, and oxidant-free protocol provides highly site-selective and efficient access to distally pyridylated alkylnitriles, which could be scale-up synthesized and readily converted

  非预功能化环状肟的新型光氧化还原-中性开环吡啶基化已通过磷酰基介导的 N O/C C 键断裂，然后进行自由基-自由基偶联来实现。这种温和的无酸、无碱和无氧化剂的方案提供了高度的位点选择性和高效的远端吡啶基化烷基腈，这些烷基腈可以按比例放大合成并很容易转化为骨架多样化的化合物。值得注意的是，通过氰基吡啶对高还原激发态光催化剂进行 SET 氧化而产生的氧化基态光催化剂可能会引发以下磷酰基介导的脱氧过程。
• Electrochemical Oxidative C−C Bond Functionalization of Methylenecyclopropanes with Diselenides/Ditellurides Leading to 2‐Substituted‐3,4‐Dihydronaphthalenes
  作者：Lei Zhan、Lei Gao、Ying‐Ming Pan、Mu‐Xue He、Xian‐Li Ma、Zu‐Yu Mo

  DOI：10.1002/adsc.202300730

  日期：2023.10.13

  This study presents an approach for the electrochemical oxidation ring-opening/cyclization reaction of methylcyclopropane with diselenides/ditellurides, leading to the synthesis of diverse 2-substituted-3,4-dihydronaphthalene derivatives with exceptional selectivity and efficiency. This methodology involves C(sp3)−H functionalization, ring opening and cyclization processes. One characteristic of this

  本研究提出了一种甲基环丙烷与二硒化物/二碲化物的电化学氧化开环/环化反应的方法，从而以优异的选择性和效率合成了多种2-取代-3,4-二氢萘衍生物。该方法涉及 C( sp 3 )−H 官能化、开环和环化过程。该方法的一个特点是它能够适应各种具有各种官能团的底物。