N-<2-(2-Phenylethynyl)phenyl>-2,2-dimethylpropanamide | 221353-38-4

• 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-<2-(2-Phenylethynyl)phenyl>-2,2-dimethylpropanamide
• 英文别名: N-[2-(phenylethynyl)phenyl]-2,2-dimethylpropanamide；N-(2-(phenylethynyl)phenyl)pivalamide；N-[2-(phenylethynyl)phenyl]pivalamide；2,2-dimethyl-N-[2-(phenylethynyl)phenyl]propanamide；2,2-dimethyl-N-[2-(2-phenylethynyl)phenyl]propanamide
• CAS: 221353-38-4
• 化学式: C₁₉H₁₉NO
• 分子量: 277.366
• InChiKey: YAESEOKMLKHDSF-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C
• 沸点：
  468.3±28.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-<2-(2-Phenylethynyl)phenyl>-2,2-dimethylpropanamide 在 palladium diacetate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以89%的产率得到(Z)-4-benzylidene-2-tert-butyl-4H-3,1-benzoxazine
  参考文献：
  名称：

  Palladium-Catalyzed Highly Regio- and Stereoselective Synthesis of 4-Alkylidene-4H-3,1-benzoxazines from N-Acyl-o-alkynylanilines

  摘要：

  The highly regio- and stereoselective 6-exo-dig mode cyclization of N-acyl-o-alkynylanilines producing 4-alkylidene-3,1-benzoxazines occurred unpredictably by use of a proper catalyst [Pd(OAc)(2)] and an effective additive (acetic acid) under suitable reaction conditions.

  DOI：

  10.1021/ol103130s
• 作为产物：
  描述：

  苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-<2-(2-Phenylethynyl)phenyl>-2,2-dimethylpropanamide
  参考文献：
  名称：

  Palladium-Catalyzed Highly Regio- and Stereoselective Synthesis of 4-Alkylidene-4H-3,1-benzoxazines from N-Acyl-o-alkynylanilines

  摘要：

  The highly regio- and stereoselective 6-exo-dig mode cyclization of N-acyl-o-alkynylanilines producing 4-alkylidene-3,1-benzoxazines occurred unpredictably by use of a proper catalyst [Pd(OAc)(2)] and an effective additive (acetic acid) under suitable reaction conditions.

  DOI：

  10.1021/ol103130s

文献信息

• Visible-light-induced tandem cyclization of 2-alkynylanilines with disulfides: a convenient method for accessing benzothiophenes under transition-metal-free and photocatalyst-free conditions
  作者：Xiaoyu Xie、Pinhua Li、Qing Shi、Lei Wang

  DOI：10.1039/c7ob01747b

  日期：——

  An efficient route to benzothiophenes via visible-light induced cyclization of 2-alkynylanilines with disulfides under transition-metal-free and photocatalyst-free conditions was developed.

  通过在无过渡金属和无光催化剂条件下，使用可见光诱导2-炔基苯胺与二硫化物进行环化反应，开发了一种有效合成苯并噻吩的方法。

• Palladium-catalyzed highly regioselective 6-exo-dig cyclization and alkenylation of ortho-ethynylanilides: the synthesis of polyene-substituted benzo[d][1,3]oxazines
  作者：Zhong-Jian Cai、Chao Yang、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1039/c5cc06510k

  日期：——

  A Pd-catalyzed highly regioselective 6-exo-dig cyclization/alkenylation reaction of ortho-ethynylanilides has been developed.

  一种钯催化的高区域选择性6-exo-dig环化/烯基化反应已经被开发出来，用于ortho-乙炔基苯胺。
• Convenient synthesis of 2-substituted indoles from 2-ethynylanilines with tetrabutylammonium fluoride
  作者：Akito Yasuhara、Yuichi Kanamori、Masashi Kaneko、Atsushi Numata、Yoshinori Kondo、Takao Sakamoto

  DOI：10.1039/a808842j

  日期：——

  The cyclization reaction of various 2-ethynylanilines, which were easily synthesized from 2-haloanilines by the palladium-catalyzed reaction with terminal alkynes, with tetrabutylammonium fluoride (TBAF) to yield 2-substituted indoles proceeded at refluxing or room temperature in THF in excellent yields without affecting the bromo, chloro, cyano, ethoxycarbonyl, and ethynyl groups.

  通过钯催化的末端炔烃与2-卤代苯胺的反应，易于合成的各种2-乙炔基苯胺，在四丁基氟化铵（TBAF）的作用下，以优异的产率在回流或室温下的四氢呋喃中进行环化反应，生成2-取代的吲哚，且不影响溴、氯、氰基、乙氧羰基和乙炔基团。
• Efficient synthesis of o-alkynyl-N-pivaloylanilines from o-acyl-N-pivaloylanilines and lithium trimethylsilyldiazomethane
  作者：Yoshiyuki Hari、Tomoki Kanie、Toyohiko Aoyama

  DOI：10.1016/j.tetlet.2005.12.051

  日期：2006.2

  Reaction of o-acyl-N-pivaloylanilines with lithium trimethylsilyldiazomethane efficiently gave the corresponding o-alkynyl-N-pivaloylanilines via alkylidenecarbene intermediates.

  邻酰基-N-新戊酰苯胺与三甲基甲硅烷基重氮甲烷锂的反应通过亚烷基卡宾中间体有效地得到了相应的邻炔基-N-新戊酰苯胺。
• Copper-Catalyzed Oxidative Ring Closure and Carboarylation of 2-Ethynylanilides
  作者：Ádám Sinai、Ádám Mészáros、Tamás Gáti、Veronika Kudar、Anna Palló、Zoltán Novák

  DOI：10.1021/ol402600r

  日期：2013.11.15

  A new copper-catalyzed oxidative ring closure of ethynyl anilides with diaryliodonium salts was developed for the highly modular construction of benzoxazines bearing a fully substituted exo double bond. The oxidative transformation includes an unusual 6-exo-dig cyclization step with the formation of C–O and C–C bonds.

  开发了一种新的铜催化的乙炔基苯胺与二芳基碘鎓盐的氧化性闭环反应，用于具有完全取代的exo双键的苯并恶嗪的高度模块化结构。氧化转化包括一个不寻常的6- exo - dig环化步骤，形成C–O和C–C键。