5-Chloro-2-(prop-1-en-2-yl)benzaldehyde | 1006685-15-9

• 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: 5-Chloro-2-(prop-1-en-2-yl)benzaldehyde
• 英文别名: 5-chloro-2-prop-1-en-2-ylbenzaldehyde
• CAS: 1006685-15-9
• 化学式: C₁₀H₉ClO
• 分子量: 180.634
• InChiKey: AFGMXZPYHAGYNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  5-Chloro-2-(prop-1-en-2-yl)benzaldehyde 在 manganese(IV) oxide 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.08h， 生成 1-(5-chloro-2-(prop-1-en-2-yl)phenyl)-3-phenylprop-2-yn-1-one
  参考文献：
  名称：

  一种获得邻萘甲酰甲基甲烷的策略：Ag（I）催化的烯酮环化反应合成苯并[ h ]苯甲撑和萘并吡啶鎓

  摘要：

  已开发出一种通过Ag（I）催化2-烯基苯基炔基酮的环化反应及其[4 + 2]与苯乙烯的环化反应，通过成环策略获得o -NQM中间体的新策略。该反应具有高效，温和的反应条件，灵活的取代和原子经济性等特点。所获得的苯并[ h ]苯并二氢吡喃产物被进一步氧化成萘并具有可调节的光物理性质。

  DOI：

  10.1021/acs.orglett.9b00281
• 作为产物：
  描述：

  2-溴-5-氯苯甲醛 、 异丙烯基硼酸 在 四(三苯基膦)钯 作用下， 生成 5-Chloro-2-(prop-1-en-2-yl)benzaldehyde
  参考文献：
  名称：

  An Efficient Three-Component One-Pot Approach to the Synthesis of 2,3,4,5-Tetrahydro-1H-2-benzazepines by Means of Rhodium-Catalyzed Hydroaminomethylation

  摘要：

  We have developed a novel and efficient three-component one-pot, catalytic approach for the synthesis of 2,3,4,5-tetrahydro-1H-2-benzazepines, using a rhodium catalyst that does not require phosphine. The isolated yields are excellent and the protocol tolerates anilines of diverse basicity.

  DOI：

  10.1021/ol702933g

文献信息

• Copper-Catalyzed Annulation–Trifluoromethyl Functionalization of Enynones
  作者：Jia-Yin Wang、Sai Zhang、Yao Tang、Shenghu Yan、Guigen Li

  DOI：10.1021/acs.orglett.3c00679

  日期：2023.4.14

  of quaternary carbon-centered 1-indanones in moderate to good chemical yields. The reaction of enynones with Togni’s reagent and chloro- or bromotrimethylsilane afforded halo- and CF3-containing 1-indenones. However, the addition of K3PO4 as a base into the catalytic system led to forming cyano-anchored (Z)-1-indanones as major stereoisomeric products. This strategy exhibits remarkable compatibility

  已经建立了 Cu(I) 催化的烯酮的环化-卤代三氟甲基化和氰基三氟甲基化，能够以中等到良好的化学产率合成以季碳为中心的 1-茚满酮的多键形成。烯酮与 Togni 试剂和氯代或溴代三甲基硅烷反应，得到含卤素和 CF 3的 1-茚酮。然而，将 K 3 PO 4作为碱添加到催化体系中导致形成氰基锚定的 ( Z )-1-茚满酮作为主要的立体异构产物。该策略表现出与多种烯酮的显着相容性。
• Continuous‐Flow Enantioselective Hydroacylations under Heterogeneous Chiral Rhodium Catalysts
  作者：Yuki Saito、Shū Kobayashi

  DOI：10.1002/anie.202313778

  日期：2024.1.2

  Heterogeneous chiral Rh catalysts were developed for continuous-flow enantioselective hydroacylations. The prepared catalysts exhibited excellent activity and enantioselectivity affording optically active ketones in quantitative yields with 99 % ee's without the leaching of Rh. The catalysts exhibited a wide substrate scope and, in sequential-flow reactions, the flow syntheses of value-added chemicals

  开发了用于连续流对映选择性加氢酰化的非均相手性 Rh 催化剂。所制备的催化剂表现出优异的活性和对映选择性，以定量产率提供光学活性酮，其 ee 为 99%，且没有 Rh 浸出。该催化剂表现出广泛的底物范围，并且在顺序流动反应中，证明了增值化学品的流动合成。
• A Strategy To Obtain <i>o</i>-Naphthoquinone Methides: Ag(I)-Catalyzed Cyclization of Enynones for the Synthesis of Benzo[<i>h</i>]chromanes and Naphthopyryliums
  作者：Feng Wu、Shifa Zhu

  DOI：10.1021/acs.orglett.9b00281

  日期：2019.3.1

  of 2-alkenylphenyl alkynyl ketones and its [4 + 2] annulations with styrenes has been developed. This reaction features high efficiency, mild reaction conditions, as well as flexible substitutions and atom economy. The obtained benzo[h]chromane products were further oxidized to naphthopyryliums, which displayed tunable photophysical properties.

  已开发出一种通过Ag（I）催化2-烯基苯基炔基酮的环化反应及其[4 + 2]与苯乙烯的环化反应，通过成环策略获得o -NQM中间体的新策略。该反应具有高效，温和的反应条件，灵活的取代和原子经济性等特点。所获得的苯并[ h ]苯并二氢吡喃产物被进一步氧化成萘并具有可调节的光物理性质。
• An Efficient Three-Component One-Pot Approach to the Synthesis of 2,3,4,5-Tetrahydro-1<i>H</i>-2-benzazepines by Means of Rhodium-Catalyzed Hydroaminomethylation
  作者：Tiago O. Vieira、Howard Alper

  DOI：10.1021/ol702933g

  日期：2008.2.1

  We have developed a novel and efficient three-component one-pot, catalytic approach for the synthesis of 2,3,4,5-tetrahydro-1H-2-benzazepines, using a rhodium catalyst that does not require phosphine. The isolated yields are excellent and the protocol tolerates anilines of diverse basicity.