4-[(4-甲氧基苯基)甲氧基]丁醛 | 119649-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[(4-甲氧基苯基)甲氧基]丁醛
• 英文名称: 4-((4-methoxybenzyl)oxy)butanal
• 英文别名: 4-(4-methoxybenzyloxy)butyraldehyde；4-[(4-methoxyphenyl)methoxy]-butanal；Butanal, 4-[(4-methoxyphenyl)methoxy]-；4-[(4-methoxyphenyl)methoxy]butanal
• CAS: 119649-27-3
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: PDTXEOPUVZXZJR-UHFFFAOYSA-N

物化性质

• 沸点：
  319.8±27.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(4-甲氧基苯基)甲氧基]丁醛 在 甲醇 、 正丁基锂 、 偶氮二甲酸二异丙酯 、 Candida antarctica lipase immobilizedon acrylic resin 、 potassium carbonate 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 异丙醚 为溶剂， 反应 23.67h， 生成 (R)-6-((4-methoxybenzyl)oxy)hex-1-yn-3-ol
  参考文献：
  名称：

  Asymmetric total synthesis of (−)-mangiferaelactone by using an appropriately substituted thiophene as a masked synthon for C-alkyl glycoside

  摘要：

  Asymmetric total synthesis of naturally occurring nonenolide (-)-mangiferaelactone was attempted through RCAM (ring closing alkyne metathesis) reaction. As the attempted RCAM reaction failed, the synthesis was finally achieved by successful exploration of a ring closing metathesis (RCM) reaction. 2-Propylthiophene was used as a masked synthon for n-heptyl glycoside, which served as main source for one of the RCM precursors and accessed by reductive desulfurization (Mozingo type reduction) of an appropriately substituted thiophene ribofuranoside. The other RCM precursor was accessed by applying an enzymatic kinetic resolution/Mitsunobu inversion sequence to an alkyne alcohol. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.06.001
• 作为产物：
  描述：

  4-甲氧基溴苄 在 草酰氯 、 sodium hydride 、 二甲基亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.17h， 生成 4-[(4-甲氧基苯基)甲氧基]丁醛
  参考文献：
  名称：

  epohelmins A，B和3-EPI的不对称合成ent- epohelmin甲

  摘要：

  这份报告详细介绍了不对称合成鹅绿素A（3），B（4）及其异构体24的有效方法。在此发散合成中的关键功能包括SMI 2诱导的交叉耦合ñ -叔-butanesulfinyl亚胺10与手性醛9源自d -苹果酸。在我们合成的鬼臼铁蛋白的合成路线中，可以级联环化至吡咯烷核骨架。另外，对于内皮素A（3）观察到了有趣的分子内oxa-Michael加成。

  DOI：

  10.1016/j.tet.2016.10.047

文献信息

• Synthesis of Ophiocerins A, B and C, Botryolide E, Decarestrictine O, Stagonolide C and 9-<i>epi</i>-Stagonolide C Employing Chiral Hexane-1,2,3,5-tetraol Derivatives as Building Blocks
  作者：Krishanu Show、Pradeep Kumar

  DOI：10.1002/ejoc.201600625

  日期：2016.9

  organocatalytic approach to the synthesis of (2R,3S)-hexane-1,2,3,5-tetraol (11) derivatives (in the forms of different stereoisomers and bearing different protecting groups) has been developed. The key chiral intermediates 11 were prepared with complete stereocontrol through the proline-catalyzed intermolecular aldol reaction between acetone and d-glyceraldehyde acetonide. The synthetic utility of the

  已开发出一种合成 (2R,3S)-己烷-1,2,3,5-四醇 (11) 衍生物（以不同立体异构体形式并带有不同保护基团）的有机催化方法。关键的手性中间体11是通过丙酮和d-甘油醛缩​​醛之间的脯氨酸催化的分子间醛醇反应在完全立体控制下制备的。通过标准合成方案将中间体转化为标题羟基化吡喃和各种不饱和内酯，证明了中间体的合成效用。
• Enantioselective ProPhenol-Catalyzed Addition of 1,3-Diynes to Aldehydes to Generate Synthetically Versatile Building Blocks and Diyne Natural Products
  作者：Barry M. Trost、Vincent S. Chan、Daisuke Yamamoto

  DOI：10.1021/ja910656b

  日期：2010.4.14

  and saturated aldehydes, of which the latter were previously limited in alkynyl zinc additions. The chiral diynol products are also versatile building blocks that can be readily elaborated; this was illustrated through highly selective trans-hydrosilylations, which enabled the synthesis of a beta-hydroxyketone and enyne. Additionally, the development of this method allowed for the rapid total syntheses

  使用我们的双核锌 ProPhenol (1) 系统开发了一种用于将末端 1,3-二炔催化加成到醛的高度对映选择性方法。此外，发现三苯基氧化膦与催化剂协同相互作用以显着增强手性识别。芳基、α、β-不饱和和饱和醛证明了这种催化转化的普遍性，其中后者以前仅限于炔基锌加成。手性二炔醇产品也是易于加工的多功能构件；这通过高度选择性的反式氢化硅烷化来说明，这使得合成 β-羟基酮和烯炔成为可能。此外，
• Formal Total Synthesis of (±)-Vindoline by Tandem Radical Cyclization
  作者：Sheng-ze Zhou、Sacha Bommezijn、John A. Murphy

  DOI：10.1021/ol0171618

  日期：2002.2.1

  A formal total synthesis of (+/-)-vindoline 1 has been achieved featuring the tandem cyclization of radicals produced from the iodoaryl azide 19a.

  已经实现了（+/-）-vindoline 1的正式全合成，其特征在于叠氮化碘代芳基叠氮化物19a产生的自由基的串联环化。
• Total Synthesis and Structural Reassignment of the γ-Lactone Polyketide from<i>Diaporthe</i>sp. SXZ-19
  作者：Jhillu S. Yadav、Palash Dutta、Bogonda Ganganna、Eedubilli Srinivas

  DOI：10.1002/ejoc.201500811

  日期：2015.11

  first stereoselective total synthesis of the proposed structure of the γ-lactone from Diaporthe sp. SXZ-19 was achieved by utilizing a convergent pathway. The four stereogenic centers were formed by employing Brown's asymmetric alkoxyallylboration reaction, and a cross-metathesis reaction was used to construct the trans double bond of the γ-lactone side chain. This synthesis led to a revision of proposed

  来自 Diaporthe sp. 的 γ-内酯的拟议结构的首次立体选择性全合成。SXZ-19 是通过利用收敛途径实现的。利用布朗的不对称烷氧基烯丙基硼化反应形成四个立体中心，并利用交叉复分解反应构建γ-内酯侧链的反式双键。这种合成导致对天然产物的拟议结构分配进行了修订。
• An improved two-step synthetic route to primary allylic alcohols from aldehydes
  作者：Zheng Liu、Yaqiong Gong、Hoe-Sup Byun、Robert Bittman

  DOI：10.1039/b9nj00710e

  日期：——

  An improved two-step synthetic route to allylic alcohols from aldehydes has been developed. A modification of the HWE reaction in H2O–2-PrOH (1 ∶ 1) and a convenient protocol to prepare AlH3 in THF from LiAlH4 and n-BuBr are the key factors in the improvement.

  开发出一种从醛合成烯丙醇的改进两步合成路线。在H2O–2-PrOH（1∶1）中对HWE反应的改良，以及从LiAlH4和n-BuBr在THF中制备AlH3的简便方案，是改进的关键因素。