(2-methoxypiperidin-1-yl)(phenyl)methanone | 63050-19-1

• 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: (2-methoxypiperidin-1-yl)(phenyl)methanone
• 英文别名: 1-benzoyl-2-methoxypiperidine；1-benzoyl-2-methoxy-piperidine；1-Benzoyl-2-methoxypiperidin；(2-Methoxypiperidin-1-yl)-phenylmethanone
• CAS: 63050-19-1
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: HTKAMCXNPVWFAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  346.3±35.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-methoxypiperidin-1-yl)(phenyl)methanone 在 氯化铵 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 N-benzoyl-3-fluoro-2-methoxypiperidine
  参考文献：
  名称：

  Diastereoselective Synthesis of 3-Fluoro-2-substituted Piperidines and Pyrrolidines

  摘要：

  A facile procedure for synthesis of trans-3-fluoro-2-substituted piperidines by utilizing electrophilic fluorination of cyclic enamines and Lewis acid mediated nucleophilic substitution has been developed. Also, optically active trans-2-allyl-3-fluorinated pyrrolidines have been prepared by utilizing nucleophilic fluorination of hydroxyl group of trans-hydroxy-L-proline and Lewis acid mediated diastereoselective allylation as key steps.

  DOI：

  10.3987/com-13-s(s)27
• 作为产物：
  描述：

  哌啶 、 靛红酸酐 在 4-二甲氨基吡啶 、 亚硝酸特丁酯 、 Eosin Y 、 对甲苯磺酸 作用下， 以 硝基甲烷 、 乙腈 为溶剂， 反应 50.0h， 生成 (2-methoxypiperidin-1-yl)(phenyl)methanone
  参考文献：
  名称：

  通过自由基易位的可见光光催化α-氨基C（sp 3）–H活化：一种新颖且不含金属的α-烷氧基苯甲酰胺方法

  摘要：

  据报道，可见光光催化，无金属合成有价值的α-烷氧基苯甲酰胺，从易制备的邻氨基苯甲酰胺和醇类通过在温和条件下的自由基易位而开始。该方案采用曙红Y作为有机光氧化还原催化剂，并采用现成的亚硝酸叔丁酯作为亚硝化试剂。这些转化在不存在任何过渡金属的情况下发生，并且以中等至良好的产率获得标题化合物。

  DOI：

  10.1016/j.tetlet.2016.02.108

文献信息

• A convenient synthetic method for amide oxidation
  作者：Gyoonhee Han、Matthias C McIntosh、Steven M Weinreb

  DOI：10.1016/s0040-4039(00)78191-3

  日期：1994.8

  Diazotization of o-aminobenzamides in methanol in the presence of a catalytic amount of CuCl affords α-methoxybenzamides in good yields.

  在催化量的CuCl存在下，将邻氨基苯甲酰胺在甲醇中重氮化，可得到高产率的α-甲氧基苯甲酰胺。
• A general method for the synthesis of indoles bearing a variety of substituents at the β-position, and its application to the synthesis of l-tryptophan
  作者：Tatsuya Shono、Yoshihiro Matsumura、Takenobu Kanazawa

  DOI：10.1016/s0040-4039(00)81629-9

  日期：1983.1

  A general synthetic method of β-substituted indoles such as indoleacetic acid, tryptamine and L-tryptophan has been exploited utilizing α-methoxylated amides, lactams, a carbamate, and sulfonamides, easily obtainable by an electrochemical method, as key intermediates.

  已经利用α-甲氧基化酰胺，内酰胺，氨基甲酸酯和磺酰胺作为关键中间体，开发了β-取代的吲哚如吲哚乙酸，色胺和L-色氨酸的一般合成方法。
• Stereoselective synthesis of azasugars by electrochemical oxidation
  作者：Shigeru Furukubo、Noriaki Moriyama、Osamu Onomura、Yoshihiro Matsumura

  DOI：10.1016/j.tetlet.2004.09.036

  日期：2004.10

  A new method using electrochemical oxidation has been exploited for the stereoselective synthesis of 2,3,6-trihydroxylated 5S-piperidine derivatives. The electrochemical method was Successively used for the conversion of N-protected piperidines to N-protected 1-methoxypiperidines and for the conversion of 1-methoxy-2,3-didehydropiperidine derivatives to 1,2,3-triacetoxypiperidine derivatives. The method provided a new synthetic route to 2S,3S,6-triacetoxy-5S-methylpiperidine and 2R,3R,6-triacetoxy-5S-methylpiperidine. (C) 2004 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of 3-deoxy-piperidine iminosugars from l-lysine
  作者：Noriaki Moriyama、Yoshihiro Matsumura、Masami Kuriyama、Osamu Onomura

  DOI：10.1016/j.tetasy.2009.11.028

  日期：2009.12

  A new method using electrochemical oxidation and/or OsO4 oxidation has been used for the stereoselective synthesis of 2,3,6-trihydroxylated (5S)-piperidine derivatives. The electrochemical method was successively used for the conversion of N-protected piperidines to N-protected 1-methoxpiperidines and for the conversion of 2,3-didehydro-1-methoxypiperidine derivatives to 2,3-trans-1,2,3-triacetoxypiperidine derivatives. These triacetates were easily transformed into (2S,3S)-6-triacetoxy-(5S)-methylpiperidine and (2R,3R)-6-triacetoxy-(5S)-methylpiperidine. In addition, the 2,3-cis-dihydroxylation of 2,3-didehydro-1-methoxypiperidine derivatives with OsO4 afforded (2R,3S)-6-triacetoxy-(5S)-methylpiperidine and (2S,3R)-(3-triacetoxy-(5S)-methylpiperidine. (C) 2009 Elsevier Ltd. All rights reserved.
• Exploratory Synthetic Studies of the α-Methoxylation of Amides <i>via</i> Cuprous Ion-Promoted Decomposition of <i>o</i>-Diazobenzamides
  作者：Gyoonhee Han、Matthew G. LaPorte、Mathias C. McIntosh、Steven M. Weinreb、Masood Parvez

  DOI：10.1021/jo961529a

  日期：1996.1.1

  A convenient nonelectrochemical amide oxidation method has been developed. The process involves a cuprous ion-promoted decomposition of o-diazobenzamides like 4, generated in situ from the corresponding o-aminobenzamides, to give N-acyliminium ion intermediate 9 via a 1,5-H-atom transfer, followed by metal-catalyzed oxidation of the resulting alpha-amidyl radical. The transformation produces alpha-methoxybenzamides 15 in good yields. An attempt was made to apply this oxidation method to a total synthesis of the alkaloid (-)-anisomycin (16). Scalemic o-aminobenzamide pyrrolidine derivatives 18a/18b underwent oxidation to give a-methoxylated amide substrates 19a/ 19b, respectively, in good yields. However, alkylation of the N-acyliminium intermediate 20 with (p-methoxybenzyl)magnesium chloride gave the undesired anti-compounds 22a/22b as the major products. The amide oxidation exhibits good regioselectivity with many unsymmetrical 2-substituted piperidine and pyrrolidine systems. In general, it appears that the larger the C-2 substituent, the greater the methylene/methine H-atom abstraction ratio. A mechanistic rationale for this selectivity is suggested based upon amide rotamer populations. An extension of this methodology can be used to conduct two sequential amide oxidations using readily prepared 2-amino-6-nitrobenzamides such as 68 and 69.