6-<(4-methoxyphenyl)methoxy>hexanal | 132131-28-3

• 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: 6-<(4-methoxyphenyl)methoxy>hexanal
• 英文别名: 6-(p-Methoxybenzyloxy)hexan-1-al；6-((4-methoxyphenyl)methoxy)hexanal；6-(4-methoxyphenylmethoxy)-1-hexanal；4-methoxybenzyl 5-formylpentyl ether；6-(4-methoxybenzyloxy)hexanal；6-[(4-Methoxyphenyl)methoxy]hexanal
• CAS: 132131-28-3
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: NVTREEQJJJVLEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  346.1±27.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-<(4-methoxyphenyl)methoxy>hexanal 在 哌啶 、 咪唑 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 N,O-双三甲硅基乙酰胺 、 草酰氯 、 水 、 二甲基亚砜 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.0h， 生成 (1S^*,9R^*)-9-(phenylsulfonyl)-7-methylene-2-hydroxybicyclo<4.3.0>nonane
  参考文献：
  名称：

  Intramolecular palladium-catalyzed trimethylenemethane cycloadditions: initial studies

  摘要：

  The potential application of [3 + 2] cycloadditions to polycarbocycle construction is considerably enhanced by the ability to perform such reactions intramolecularly. The feasibility of such processes is explored in the context of Pd-catalyzed cycloadditions of 2-[(trimethylsilyl)methyl]allyl carboxylates, wherein trimethylenemethane (TMM) precursor fragment (donor) and the electron-deficient olefin (acceptor) is joined by a tether of simple methylene groups of 3, 4, 5, and 8 members. Several versatile synthetic routes to these substrates were developed. 2-Bromo-3-(trimethylsilyl)propene proves to be a key reagent for construction of the donor portion. Acceptors bearing esters, cyano groups, and especially sulfones have been examined. The diastereoselectivity of the reaction has been explored both in terms of ring juncture and the diastereofacial selectivity with respect to an oxygen substituent at the allylic position of the acceptor. Excellent cycloadditions to give the bicyclo[3.3.0] octyl and bicyclo[4.3.0]nonyl systems are observed, whereas larger rings cannot be obtained in this series. The choice of catalyst proves critical, the most useful being either tetrakis(triphenylphosphine)palladium and DPPE or, more generally, triisopropyl phosphite and palladium acetate. The first cycloaddition of a 1,1-dialkylated TMM precursor, which fails in intermolecular cases, has been observed in this intramolecular series to give a bridgehead-substituted bicycle. A rationale for the observed diastereoselectivity is presented.

  DOI：

  10.1021/ja00019a036
• 作为产物：
  描述：

  1,6-己二醇 在 sodium hydride 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 26.5h， 生成 6-<(4-methoxyphenyl)methoxy>hexanal
  参考文献：
  名称：

  PMB 醚的有氧氧化制羧酸

  摘要：

  以 Fe（NO3）3 ⋅ 9H2O 和 TEMPO 为助催化剂，以氧为绿色氧化剂，PMB 醚在室温下以高效率和选择性转化为羧酸。通过将该方案作为关键步骤，已经实现了天然存在的 （R）-6-羟基-7,9-十八烷二炔酸的完全合成。基于仔细研究，已经提出了一种涉及氧稳定苄基阳离子的机制。

  DOI：

  10.1002/chem.202401815

文献信息

• Fluorinated Musk Fragrances: The CF₂Group as a Conformational Bias Influencing the Odour of Civetone and (<i>R</i>)-Muscone
  作者：Ricardo Callejo、Michael J. Corr、Mingyan Yang、Mingan Wang、David B. Cordes、Alexandra M. Z. Slawin、David O'Hagan

  DOI：10.1002/chem.201600519

  日期：2016.6.6

  over edge locations in aliphatic macrocycles. In this study, the CF2 group has been introduced into musk relevant macrocyclic ketones. Nine civetone and five muscone analogues have been prepared by synthesis for structure and odour comparisons. X‐ray studies indeed show that the CF2 groups influence ring structure and they give some insight into the preferred ring conformations, triggering a musk odour

  二氟亚甲基（CF 2）基团在脂族大环化合物中具有在边缘位置转角的强烈趋势。在这项研究中，CF 2基已被引入到麝香相关的大环酮中。通过合成制备了九个西维酮和五个麝香酮类似物，用于结构和气味比较。X射线研究确实表明，CF 2基团会影响环的结构，并且使他们对首选的环构型有一些了解，从而触发了在专业香水环境中确定的麝香味。Bersuker及其同事对麝香香精的历史构象模型通常保持不变，并且由于CF 2的特殊放置而使结构偏离了这一共识。 群体，失去麝香的香味，变得不那么愉快。
• A general approach to medium-sized ring ethers via hydrolytic and oxidative kinetic resolutions: stereoselective syntheses of (−)-cis-lauthisan and (+)-isolaurepan
  作者：Divya Tripathi、Satyendra Kumar Pandey、Pradeep Kumar

  DOI：10.1016/j.tet.2009.01.062

  日期：2009.3

  A short and enantioselective approach to medium ring ethers and its application to the syntheses of (−)-cis-lauthisan and (+)-isolaurepan are described. The synthetic strategy features Jacobson's Hydrolytic Kinetic Resolution (HKR), oxidative resolution of secondary alcohol, and highly diastereoselective Et3SiH/TMSOTf-promoted reductive cyclization of a hydroxy ketone to give exclusively the different

  描述了一种对中环醚的短而对映选择性的方法及其在合成（-）-顺式-月桂聚糖和（+）-异硫脲中的应用。合成策略具有Jacobson的水解动力学拆分（HKR），仲醇的氧化拆分和高度非对映选择性的Et 3 SiH / TMSOTf促进的羟基酮还原环化作用，从而仅产生不同的中等大小的顺式-二取代的环醚。
• Stereocontrolled Total Synthesis of Nonenolide
  作者：Purushotham Reddy Sudina、Damoder Reddy Motati、Aravind Seema

  DOI：10.1021/acs.jnatprod.8b00001

  日期：2018.6.22

  against Plasmodium falciparum K1. Structurally, it features a decanolide with a trans-double bond attached to two chiral hydroxy groups, making the total synthesis of the exclusive isomer of 1 more difficult. Herein, we report the successful synthesis of 1 by employing a MacMillan α-hydroxylation to generate three chiral centers in both the key fragments, starting from 1,6-hexanediol and 1,4-butanediol

  Nonnolide（1）首先从昆虫病原菌虫草虫草BCC2816中分离出来，对恶性疟原虫K1表现出良好的抗疟活性。在结构上，它的特征是癸醇化物具有连接到两个手性羟基上的反式双键，这使得1的排他异构体的全合成更加困难。本文中，我们报道了通过MacMillanα-羟基化反应成功合成1的过程，在两个关键片段中生成了三个手性中心，从1,6-己二醇和1,4-丁二醇开始，然后进行Steglich酯化化合物2和3。独家E异构体是通过单-PMB-保护的二烯19的闭环复分解获得的。脱保护得到所需的天然产物1。
• Fluorine in fragrances: exploring the difluoromethylene (CF₂) group as a conformational constraint in macrocyclic musk lactones
  作者：Michael J. Corr、Rodrigo A. Cormanich、Cortney N. von Hahmann、Michael Bühl、David B. Cordes、Alexandra M. Z. Slawin、David O'Hagan

  DOI：10.1039/c5ob02023a

  日期：——

  The synthesis of a series of selectively fluorinated musk lactones is reported with CF₂ groups at various locations to bias conformation the ring.

  报道了一系列有选择性氟化的麝香内酯的合成，其中在不同位置有CF₂基团以偏向构象环。
• Selective Long-Distance Isomerization of Terminal Alkenes via Nondissociative Chain Walking
  作者：Yuya Yamasaki、Takaaki Kumagai、Shota Kanno、Fumitoshi Kakiuchi、Takuya Kochi

  DOI：10.1021/acs.joc.8b01288

  日期：2018.8.17

  Selective long-distance isomerization of terminal alkenes to silyl enol ethers proceeded via nondissociative chain walking using phenanthroline palladium catalysts. Notable features achieved taking advantage of the nondissociative chain walking mechanism include high efficiency obtained regardless of the chain length, high chemoselectivity toward terminal alkenes over internal ones, and retention of

  末端烯烃向甲硅烷基烯醇醚的选择性长距离异构化是通过使用菲咯啉钯催化剂的非解离链走进行的。利用非解离链行走机制获得的显着特征包括无论链长如何都获得了高效率，相对于内部烯烃对末端烯烃的高化学选择性以及在烷基链上保留了立体中心的立体构型。