2-(2-oxo-2-phenylethyl)octanal | 1221505-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-oxo-2-phenylethyl)octanal
• 英文别名: 2-Phenacyloctanal；2-phenacyloctanal
• CAS: 1221505-19-6
• 化学式: C₁₆H₂₂O₂
• 分子量: 246.349
• InChiKey: NKMHFARGXSDPKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙烯 、 正辛醛 在 吡咯烷盐酸盐 、 manganese(IV) oxide 、 copper(II) perchlorate hexahydrate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以56%的产率得到2-(2-oxo-2-phenylethyl)octanal
  参考文献：
  名称：

  The cascade carbo-carbonylation of unactivated alkenes catalyzed by an organocatalyst and a transition metal catalyst: a facile approach to γ-diketones and γ-carbonyl aldehydes from arylalkenes under air

  摘要：

  一种新颖的级联碳羰基化反应，利用有机催化剂和过渡金属催化剂，在空气中通过SOMO-烯胺催化未活化芳基烯烃与酮或醛发生反应。

  DOI：

  10.1039/b921310d

文献信息

• Spin-Center Shift-Enabled Direct Enantioselective α-Benzylation of Aldehydes with Alcohols
  作者：Eric D. Nacsa、David W. C. MacMillan

  DOI：10.1021/jacs.7b12768

  日期：2018.3.7

  two-electron pathways. We report herein an enantioselective α-benzylation of aldehydes using alcohols as alkylating agents based on the mechanistic principle of spin-center shift. This strategy harnesses the dual activation modes of photoredox and organocatalysis, engaging the alcohol by SCS and capturing the resulting benzylic radical with a catalytically generated enamine. Mechanistic studies provide

  大自然通常使用醇作为离去基团，因为 DNA 生物合成依赖于通过自由基介导的“自旋中心转移”（SCS）机制从核糖核苷二磷酸中去除水。然而，由于醇在双电子途径中的低反应性，醇在合成化学中作为烷化剂仍然没有得到充分利用。我们在此报告了基于自旋中心位移的机械原理，使用醇作为烷化剂的醛的对映选择性 α-苄基化。该策略利用光氧化还原和有机催化的双重激活模式，通过 SCS 与醇结合，并用催化生成的烯胺捕获产生的苄基自由基。机理研究为 SCS 作为关键的基本步骤提供了证据，确定了竞争反应的起源，
• Lead-Halide Perovskites for Photocatalytic α-Alkylation of Aldehydes
  作者：Xiaolin Zhu、Yixiong Lin、Yue Sun、Matthew C. Beard、Yong Yan

  DOI：10.1021/jacs.8b08720

  日期：2019.1.16

  Cost-effective and efficient photocatalysis are highly desirable in chemical synthesis. Here we demonstrate that readily prepared suspensions of APbBr3 (A = Cs or methylammonium (MA)) type perovskite colloids (ca. 2-100 nm) can selectively photocatalyze carbon-carbon bond formation reactions, i.e., α-alkylations. Specifically, we demonstrate α-alkylation of aldehydes with a turnover number (TON) of

  在化学合成中非常需要具有成本效益和高效的光催化。在这里，我们证明容易制备的 APbBr3（A = Cs 或甲基铵（MA））型钙钛矿胶体（约 2-100 nm）悬浮液可以选择性地光催化碳-碳键形成反应，即α-烷基化。具体来说，我们展示了醛的 α-烷基化，在可见光照射下，周转数 (TON) 超过 52,000。混合有机/无机钙钛矿正在彻底改变光伏研究，现在正在影响其他研究领域，但它们在有机合成方面的探索很少见。我们的低成本、易于加工、高效且能带可调的钙钛矿光催化剂有望为化学合成带来新的见解。
• Light-Driven Organocatalysis Using Inexpensive, Nontoxic Bi₂O₃as the Photocatalyst
  作者：Paola Riente、Alba Matas Adams、Josep Albero、Emilio Palomares、Miquel A. Pericàs

  DOI：10.1002/anie.201405118

  日期：2014.9.1

  enantioselective catalytic processes that make use of sunlight as the energy source and nontoxic, affordable materials as catalysts represents one of the new and rapidly evolving areas in chemical research. The direct asymmetric α‐alkylation of aldehydes with α‐bromocarbonyl compounds can be successfully achieved by combining bismuth‐based materials as low‐band‐gap photocatalysts with the second‐generation MacMillan

  利用太阳光作为能源，使用无毒，负担得起的材料作为催化剂的对映选择性催化方法的发展，代表了化学研究领域中迅速发展的新领域之一。通过将基于铋的材料作为低带隙光催化剂与第二代MacMillan咪唑啉酮作为手性催化剂以及模拟阳光作为低成本和低价有机物相结合，可以成功实现醛与α-溴羰基化合物的直接不对称α-烷基化反应。清洁能源。当反应小瓶在西班牙塔拉戈纳的一个晴朗的9月天暴露在早晨的阳光下时，该反应也能高效进行。
• Lead‐Free Cs ₂ AgSbCl ₆ Double Perovskite Nanocrystals for Effective Visible‐Light Photocatalytic C−C Coupling Reactions
  作者：Yanmei Guo、Yongbing Lou、Jinxi Chen、Yixin Zhao

  DOI：10.1002/cssc.202102334

  日期：2022.2.8

  AbstractLead halide perovskite nanocrystals (NCs) have been regarded as a promising potential photocatalyst, owing to their high molar extinction coefficient, low economic cost, adjustable light absorption range, and ample surface active sites. However, the toxicity of lead and its inherent instability in water and polar solvents could hinder their wide application in the field of photocatalysis. Herein, with α‐alkylation of aldehydes as a model reaction, C−C bond‐forming is demonstrated in high yield by using lead‐free double perovskite Cs2AgSbCl6 NCs under visible light irradiation. Moreover, the photocatalytic performance is simply improved by rational control of the surface ligands and a reaction mechanism involving a radical intermediate is proposed. Although the stability requires further amelioration, the results indicate the enormous potential of lead‐free double perovskite NC photocatalysts for organic synthesis and chemical transformations.
• The cascade carbo-carbonylation of unactivated alkenes catalyzed by an organocatalyst and a transition metal catalyst: a facile approach to γ-diketones and γ-carbonyl aldehydes from arylalkenes under air
  作者：Jin Xie、Zhi-Zhen Huang

  DOI：10.1039/b921310d

  日期：——

  A novel cascade carbon-carbonylation reaction of unactivated arylalkenes with ketones or aldehydes was catalyzed by an organocatalyst and a transition metal catalyst via a SOMO-enamine under air.

  一种新颖的级联碳羰基化反应，利用有机催化剂和过渡金属催化剂，在空气中通过SOMO-烯胺催化未活化芳基烯烃与酮或醛发生反应。