3-(m-Methoxyphenyl)butanal | 113504-55-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(m-Methoxyphenyl)butanal
• 英文别名: 3-(3-methoxyphenyl)butanal；dl-3-(m-methoxyphenyl)-butanal
• CAS: 113504-55-5
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: RMHHYUNPRHOGBA-UHFFFAOYSA-N

物化性质

• 沸点：
  257.3±23.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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-(m-Methoxyphenyl)butanal 生成 N-<6-(m-Methoxyphenyl)hept-3-(Z)-enyl>succinimide
  参考文献：
  名称：

  TREHAN, I. R.;KAD, G. L.;SINGH, JANGBIR;GUPTA, SANGITA;BALA, RENU, INDIAN J. CHEM., 26,(1987) N 3, 212-215

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(m-methoxyphenyl)butanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到3-(m-Methoxyphenyl)butanal
  参考文献：
  名称：

  Trehan, I. R.; Kad, G. L.; Singh, Jangbir, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 212 - 215

  摘要：

  DOI：

文献信息

• Pd-Catalyzed Arylation of 1,2-Amino Alcohol Derivatives via β-Carbon Elimination
  作者：Miquel A. Pericàs、Ruben Martin、Miriam Sau

  DOI：10.1055/a-1699-4766

  日期：2022.1

  AbstractHerein, we describe a Pd-catalyzed arylation of 1,2-amino alcohols with aryl halides enabled by a retroallylation manifold. This protocol constitutes a new entry point to β-arylated aldehydes via the intermediacy of in situ generated enamine intermediates. The protocol is characterized by its exquisite regioselectivity profile and broad substrate scope – including challenging substrate combinations

  摘要在此，我们描述了通过逆芳基化歧管实现的 1,2-氨基醇与芳基卤化物的 Pd 催化芳基化。该协议通过原位生成的烯胺中间体的中间体构成了 β-芳基化醛的新切入点。该协议的特点是其精细的区域选择性分布和广泛的底物范围 - 包括具有挑战性的底物组合 - 即使以对映选择性的方式也是如此。
• Linear Selective Hydroformylation of 2‐Arylpropenes Using Water‐Soluble Rh‐PNP Complex: Straightforward Access to 3‐Aryl‐Butyraldehydes
  作者：Tong Ru、Guanfeng Liang、Luyun Zhang、Yingtang Ning、Fen‐Er Chen

  DOI：10.1002/cctc.202101352

  日期：2021.12.15

  Rh-catalyzed hydroformylation of 2-arylpropenes becomes available using an unprecedented PNP ligand. The protocol provides a powerful strategy to access a wide library of 3-aryl-butyraldehydes with excellent selectivity and scalability. A concise total synthesis of rac-ar-turmerone is also pursued to demonstrate the practical nature of this protocol.

  使用前所未有的 PNP 配体，可以实现 2-芳基丙烯的 Rh 催化加氢甲酰化。该协议提供了一种强大的策略来访问具有出色选择性和可扩展性的广泛的 3-芳基丁醛库。还追求rac-ar-姜黄酮的简明全合成，以证明该协议的实用性。
• Generality and mechanism of homobenzylic-homoallylic hydrogenolysis of 5-aryl-4,5-dihydro-1,3-dioxepins
  作者：Kiyohiro Samizu、Kunio Ogasawara

  DOI：10.1016/0040-4039(94)80030-8

  日期：1994.10

  Birch reduction of several 5-aryl-4,5-dihydro-1,3-dioxepins gave rise to 3-arylbutanal in moderate to good yields by hydrogenolytic cleavage of the homobenzylic-homoallylic carbonoxygen bond when the benzylic-allylic carbon is tertiary. However, the reaction did not take place when the benzylic-allylic carbon is quaternary. Moreover, the reaction was found to proceed with complete racemization at

  当苄基-烯丙基碳为叔碳时，通过氢解裂解均苄基-均烯丙基碳-氧键，桦木还原几种5-芳基-4,5-二氢-1,3-二氧杂环丁烷可以中等至良好的收率得到3-芳基丁醛。 。但是，当苄基烯丙基碳为季铵盐时，该反应没有发生。此外，发现该反应在苄基烯丙基中心完全消旋地进行，表明涉及同时发生的消除-还原途径。
• Nonsilyl Bicyclic Secondary Amine Catalysts for the Asymmetric Transfer Hydrogenation of α,β-Unsaturated Aldehydes
  作者：Rohtash Kumar、Vidyasagar Maurya、Avinash Avinash、Chandrakumar Appayee

  DOI：10.1021/acs.joc.4c00523

  日期：2024.6.21

  amine organocatalysts and their application to the asymmetric transfer hydrogenation of α,β-unsaturated aldehydes are disclosed. A lower catalytic loading (5 mol %) is demonstrated for the reduction of a wide range of α,β-unsaturated aldehydes (up to 97% yield and up to 99% ee). The application of this scalable methodology is showcased for the asymmetric synthesis of bioactive molecules such as phenoxanol

  公开了非甲硅烷基双环仲胺有机催化剂的首次手性合成及其在α,β-不饱和醛不对称转移氢化中的应用。较低的催化负载量 (5 mol%) 可还原多种 α,β-不饱和醛（产率高达 97%， ee高达 99%）。展示了这种可扩展方法在苯恶醇、香茅醇、雷美替胺和特立卡兰等生物活性分子的不对称合成中的应用。
• Enantioselective Functionalization of Inactive sp³ C–H Bonds Remote to Functional Group by Metal/Organo Cooperative Catalysis
  作者：Xiao-Le Zhou、Pu-Sheng Wang、Da-Wei Zhang、Peng Liu、Cheng-Ming Wang、Liu-Zhu Gong

  DOI：10.1021/acs.orglett.5b02653

  日期：2015.10.16

  A metal/organo cooperative catalysis to enable the enantioselective functionalization of inactive C-H bonds gamma to the formyl group in aliphatic aldehydes has been established. Instead of using enals as substrates in traditional organocatalytic cydization reactions, the aliphatic aldehydes directly participated in [4 + 2] cyclization with quinone derivatives exploiting molecular oxygen as oxidants to afford optically active cyclic molecules with excellent levels of enantioselectivity. This method features a combination of pot, step, and atom economy.