N-(1-ethoxy-1-phenylmethyl)benzamide | 15563-54-9

• 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: N-(1-ethoxy-1-phenylmethyl)benzamide
• 英文别名: N-(ethoxy(phenyl)methyl)benzamide；N-(α-Ethoxybenzyl)-benzamid；N-[ethoxy(phenyl)methyl]benzamide
• CAS: 15563-54-9
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: JDYNIODNHXGDKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1-ethoxy-1-phenylmethyl)benzamide 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2'S,2R,3S,5S)-acetic acid 2-acetoxymethyl-5-(benzoylamino-phenylmethyl)-6-ethoxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Highly Facialselective Synthesis of Pyranose 1,3-Oxazines and Their Ring Opening with Nucleophiles: A Novel Entry to 2-C-Branched Glycosides

  摘要：

  A TMSOTf-promoted cycloaddition of N-benzoyl-N,O-acetals with various glycals and 3-deoxy glycals affords pyranose 1,3-oxazines with high facial selectivity. In addition, a highly diastereoselective ring opening of the resulting pyranose 1,3-oxazines is reported. With diverse nucleophiles, these reactions take place upon heating at 80 degrees C. This novel ring-opening reaction affords structurally diversified 2-C-branched glycosides with three newly formed contiguous stereocenters.

  DOI：

  10.1021/ol2019604
• 作为产物：
  描述：

  N,N'-benzylidene bisbenzamide 生成 N-(1-ethoxy-1-phenylmethyl)benzamide
  参考文献：
  名称：

  N-苄基苯甲亚胺和N-α-烷氧基苄基苯甲酰胺

  摘要：

  亚苄基双苯甲酰胺（I）的热分解得到N-苯甲酰基苯甲二胺（II）。描述了乙二酰亚胺及其甲醇加成产物（IV）的一些化学和光谱性质。

  DOI：

  10.1016/0040-4020(67)85153-6

文献信息

• Synthesis of <i>N</i>-Acyl-<i>N</i>,<i>O</i>-acetals Mediated by Titanium Ethoxide
  作者：Min Li、Bingling Luo、Qi Liu、Yumin Hu、A. Ganesan、Peng Huang、Shijun Wen

  DOI：10.1021/ol4031155

  日期：2014.1.3

  functional group can act as a synthetic precursor to unstable reactive N-acylimines. In this paper, a variety of N-acyl-O-ethyl-N,O-acetals was concisely prepared under mild conditions mediated by titanium ethoxide (Ti(OEt)4). The method also offers a new strategy to make other O-alkyl-N,O-acetals. Furthermore, this strategy was extended to the synthesis of an analogue of the natural product turtschamide

  N-酰基-N，O-缩醛存在于许多具有生物活性的天然产物中，并且这种不寻常的官能团可以充当不稳定的反应性N-酰基酰亚胺的合成前体。本文在乙醇钛（Ti（OEt）4）介导的温和条件下，简明地制备了各种N-酰基-O-乙基-N，O-缩醛。该方法还提供了制备其他O-烷基-N，O-乙缩醛的新策略。此外，该策略扩展到了天然产物turtschamide的类似物的合成。
• Enantioselective Peroxidation of <i>C</i>-alkynyl imines enabled by chiral BINOL calcium phosphate
  作者：Zhongwen Sun、Lijun Chen、Kaixiong Qiu、Bo Liu、Hongtao Li、Fang Yu

  DOI：10.1039/d1cc07156d

  日期：——

  Herein, we report a catalytic enantioselective addition of C-alkynyl imines with hydroperoxides catalyzed by chiral BINOL calcium phosphate, affording a broad range of enantioenriched α-peroxy propargylamines in good yields (80–99%) with high enantioselectivities (up to 94% ee). The protocol is characterized by mild conditions, easy accessibility and good practicability.

  在此，我们报道了由手性 BINOL 磷酸钙催化的C-炔基亚胺与氢过氧化物的催化对映选择性加成，以良好的收率（80-99%）和高对映选择性（高达 94% ee）提供范围广泛的对映富集的 α-过氧炔丙基胺）。该协议具有条件温和、易于获取、实用性强的特点。
• Aziridination of Activated Imines with Monocarbonyl Iodonium Ylides Generated from (<i>Z</i>)-(2-Acetoxyvinyl)iodonium Salts via Ester Exchange:  Stereoselective Synthesis of 2-Acylaziridines
  作者：Masahito Ochiai、Yutaka Kitagawa

  DOI：10.1021/jo982346m

  日期：1999.4.1

  Monocarbonyl iodonium ylides, generated in situ from (Z)-(2-acetoxyvinyl)iodonium salts via an ester exchange reaction with EtOLi, undergo alkylidene transfer reactions to activated imines yielding 2-acylaziridines in good yields. The stereochemical outcome of this aziridination was shown to be dependent on both the activating groups of the imines and the reaction solvents: that is, the aziridination

  由（Z）-（2-乙酰氧基乙烯基）碘鎓盐通过与EtOLi的酯交换反应原位生成的单羰基碘鎓烷基化物经过亚烷基转移到活化的亚胺上，生成高产率的2-酰基氮丙啶。已显示出这种叠氮化的立体化学结果取决于亚胺的活化基团和反应溶剂：也就是说，N-（2,4,6-三甲基苯磺酰基）亚胺在THF中的叠氮化提供了顺式叠氮基而在THF-DMSO或THF中，N-苯并嘧啶的主要产物可立体选择性地产生反式异构体。
• A Highly Diastereoselective Access to Silicon-Containing Oxazines via the TMSOTf-Promoted Reactions of N-Benzoyl-N,O-acetals with Allyl Silanes
  作者：Biao-Lin Yin、Zheng-Rong Li、Yuan-Xiu Zhang、Wei-Ping Tu

  DOI：10.1055/s-0031-1289877

  日期：2011.12

  TMSOTf-promoted cycloaddition of N-benzoyl-N,O-acetals with allyl silanes to synthesize silicon-containing oxazines with high diastereoselectivities has been developed. The obtained products might be useful as building blocks in organic synthesis. N-benzoyl-N,O-acetals - oxazine - cycloaddition - dia­stereoselectivity

  已经开发出TMSOTf促进N-苯甲酰基-N，O-缩醛与烯丙基硅烷的环加成反应，以合成具有高非对映选择性的含硅恶嗪。所得产物可能用作有机合成的基础。 N-苯甲酰-N，O-缩醛 -恶嗪-环加成-非对映选择性
• N-[1-(Benzotriazol-1-yl)alkyl]amides, versatile amidoalkylation reagents. 5. A general and convenient route to N-(.alpha.-alkoxyalkyl)amides
  作者：Alan R. Katritzky、Wei Qiang Fan、Michael Black、Juliusz Pernak

  DOI：10.1021/jo00028a028

  日期：1992.1

  N-[1-(Benzotriazol-1-yl)alkyl]amides 2, easily prepared from benzotriazole 1, an aldehyde, and an amide, react readily with a variety of primary and secondary alcohols under mild conditions to give N-(alpha-alkoxyalkyl)amides 3 in good yield.