N-cinnamylbenzamide | 63163-63-3

• 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: N-cinnamylbenzamide
• 英文别名: N-(3-Phenylprop-2-en-1-yl)benzamide；N-(3-phenylprop-2-enyl)benzamide
• CAS: 63163-63-3
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: IIGRIEOYTAFIEO-UHFFFAOYSA-N

物化性质

• 熔点：
  95 °C
• 沸点：
  468.7±34.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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-cinnamylbenzamide 在 碘代三甲硅烷 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以72%的产率得到5-(iodo(phenyl)methyl)-2-phenyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Modular Preparation of 5-Halomethyl-2-oxazolines via PhI(OAc)₂-Promoted Intramolecular Halooxygenation of N-Allylcarboxamides

  摘要：

  A new method for the construction of oxazoline moiety was detailed. Using (diacetoxyiodo)benzene (PIDA) as the reaction promoter and halotrimethylsilane as the halogen source, intramolecular halooxygenation and halothionation of N-allylcarboxamides/N-allylcarbothioamides proceeded readily, leading : to the corresponding 5-halomethyloxazolines/5-halomethylthiazolines in good to excellent isolated yields. The 5-halomethyl products could be converted to different derivatives via conventional nucleophilic substitution methods. The reactions were carried out using easily available starting materials, and did not need harsh reaction conditions. All these features made this reaction a viable method for the construction of different oxazoline and thiazoline structures.

  DOI：

  10.1021/acs.joc.5b01832
• 作为产物：
  描述：

  肉桂基氯 在 sodium hydroxide 、 乙醇 、 氨 作用下， 生成 N-cinnamylbenzamide
  参考文献：
  名称：

  Posner, Chemische Berichte, 1893, vol. 26, p. 1860

  摘要：

  DOI：

文献信息

• Desymmetrization of Bisallylic Amides through Catalytic Enantioselective Bromocyclization with BINAP Monoxide
  作者：Yoshihiro Nagao、Tatsunari Hisanaga、Hiromichi Egami、Yuji Kawato、Yoshitaka Hamashima

  DOI：10.1002/chem.201704847

  日期：2017.11.27

  We report the first desymmetrization of bisallylic amides by enantioselective bromocyclization with BINAP monoxide as a catalyst. Depending upon the substitution pattern of the alkene moieties, densely functionalized, optically active oxazoline or dihydrooxazine compounds were obtained in a highly stereoselective manner. The remaining alkene moiety was subjected to various functional group manipulations

  我们报道了通过以BINAP一氧化碳为催化剂的对映选择性溴环化的双烯丙基酰胺的第一次去对称化。取决于烯烃部分的取代模式，以高度立体选择性的方式获得了稠密官能化的，光学活性的恶唑啉或二氢恶嗪化合物。其余的烯烃部分经过各种官能团处理，以提供具有多个立体中心的多种手性分子阵列。
• Dianionic Phase-Transfer Catalyst for Asymmetric Fluoro-cyclization
  作者：Hiromichi Egami、Tomoki Niwa、Hitomi Sato、Ryo Hotta、Daiki Rouno、Yuji Kawato、Yoshitaka Hamashima

  DOI：10.1021/jacs.7b13690

  日期：2018.2.28

  dicationic nature of the electrophilic fluorinating reagent, Selectfluor (1), we rationally designed a series of dicarboxylic acid precatalysts (2), which, when deprotonated, act as anionic phase-transfer catalysts for asymmetric fluorination of alkenes. Among them, 2a having the shortest linker moiety efficiently catalyzed unprecedented 6-endo-fluoro-cyclization of various allylic amides, affording

  受亲电氟化试剂 Selectfluor (1) 的双阳离子性质的启发，我们合理设计了一系列二羧酸预催化剂 (2)，当去质子化时，它们作为阴离子相转移催化剂用于烯烃的不对称氟化。其中，具有最短连接体部分的 2a 有效地催化了各种烯丙基酰胺的前所未有的 6-内氟环化，得到了具有高对映选择性（高达 99% ee）的氟化二氢恶嗪化合物。除环状底物外，无环三取代烯烃以良好的非对映选择性进行反应，而线性二取代烯烃的非对映选择性较低。结果表明反应通过氟碳正离子中间体进行。
• Organocatalytic synthesis of amides from nitriles via the Ritter reaction
  作者：Samad Khaksar、Eskandar Fattahi、Esmail Fattahi

  DOI：10.1016/j.tetlet.2011.08.121

  日期：2011.11

  environmentally friendly, and efficient route for the synthesis of a wide variety of amides in high yields via the Ritter reaction of alcohols with nitriles has been demonstrated. Pentafluorophenyl ammonium triflate (PFPAT) is used as an organocatalyst and is air-stable, cost-effective, easy to handle, and easily removed from the reaction mixtures.

  已经证明了通过醇与腈的Ritter反应以高产率合成多种酰胺的简单，廉价，环境友好和有效的途径。五氟苯基三氟甲磺酸铵（PFPAT）用作有机催化剂，对空气稳定，成本效益高，易于处理并且易于从反应混合物中除去。
• Rh(III) and Ir(III)Cp* Complexes Provide Complementary Regioselectivity Profiles in Intermolecular Allylic C–H Amidation Reactions
  作者：Jacob S. Burman、Robert J. Harris、Caitlin M. B. Farr、John Bacsa、Simon B. Blakey

  DOI：10.1021/acscatal.9b01338

  日期：2019.6.7

  regioselective allylic C–H amidation of mono-, di-, and trisubstituted olefins has been developed. Specifically, the combination of dioxazolone reagents with RhCp* and IrCp* catalysts is reported to promote reactions with complementary regioselectivites to those previously observed in Pd-catalyzed and Ag-promoted Rh-catalyzed reactions. We report that catalyst matching with substrate class is essential for

  已经开发出一种有效的区域选择性的单，双和三取代烯烃的区域芳族CHH酰胺化方法。具体而言，据报道，二恶唑酮试剂与RhCp *和IrCp *催化剂的组合可促进与互补区域选择性反应的反应，与先前在Pd催化和Ag促进的Rh催化反应中观察到的反应相同。我们报告说，与底物类别匹配的催化剂对于选择性反应是必不可少的。RhCp *络合物对于高转化率和与β-烷基苯乙烯底物的选择性是必需的，而IrCp *络合物在未活化的末端烯烃的情况下是必需的。
• CuBr 2 -promoted intramolecular bromocyclization of N-allylamides and aryl allyl ketone oximes
  作者：Chun-Hua Yang、Zhong-Qi Xu、Lili Duan、Yue-Ming Li

  DOI：10.1016/j.tet.2017.10.025

  日期：2017.11

  A new and easy-to-perform route to 2-oxazolines amd isoxazolines was reported. Using CuBr2 as both the bromide source and the reaction promoter, bromocyclization of N-allylamides and allyl ketone oximes proceeded readily, leading to oxazolines and isoxazolines in good to excellent yields.

  据报道，有一条新的且易于执行的方法合成2-恶唑啉和异恶唑啉。使用CuBr 2作为溴化物源和反应促进剂，N-烯丙酰胺和烯丙基酮肟的溴环化反应容易进行，从而产生了恶唑啉和异恶唑啉，收率良好至极佳。