(E)-N,N-dimethyl-2-hexenamide | 97253-75-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-N,N-dimethyl-2-hexenamide
• 英文别名: (E)-N,N-dimethylhex-2-enamide
• CAS: 97253-75-3
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: VRMAYTVPFSSPPP-VOTSOKGWSA-N

物化性质

• 沸点：
  242.6±9.0 °C(Predicted)
• 密度：
  0.890±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N,N-dimethyl-2-hexenamide 在 叔丁基过氧化氢 三苯胂氧化物 、 S-1,1'-联-2-萘酚 、 samarium(III) isopropoxide 作用下， 以 四氢呋喃 、 癸烷 为溶剂， 反应 6.0h， 生成 (2R,3S)-3-Propyl-oxirane-2-carboxylic acid dimethylamide
  参考文献：
  名称：

  Dynamic Ligand Exchange of the Lanthanide Complex Leading to Structural and Functional Transformation:  One-Pot Sequential Catalytic Asymmetric Epoxidation-Regioselective Epoxide-Opening Process

  摘要：

  The characteristic property of the lanthanide complex, which easily undergoes a dynamic ligand exchange and alters its structure and function in situ, is described. After the completion of the catalytic asymmetric epoxidation of various a,beta-unsaturated amides 2 in the presence of the Sm-(S)-BINOL-Ph3As=O (1:1:1) complex 1 (2-10 mol %), the addition of Me3SiN3 directly to the reaction mixture led to smooth epoxide-opening at room temperature, affording the corresponding anti-beta-azido-alpha-hydroxyamide 4 in excellent overall yield (up to 99%) with complete regioselectivity and excellent enantiomeric excess (up to >99%). The key to the success of the sequential process was the in situ generation of the highly reactive samarium azide complex through dynamic ligand exchange. In situ IR spectroscopy and other experiments provided strong evidence that the samariurn azide complex was generated. In addition, the relatively high Lewis basicity of the amide moiety had a key role in the high reactivity of both the epoxidation and the epoxide-opening reactions. Examinations of other nucleophiles such as sulfur or carbon nucleophiles as well as transformations of epoxide-opened products are also described.

  DOI：

  10.1021/ja043770+
• 作为产物：
  描述：

  (Z)-2-己烯酸 在 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.75h， 生成 (E)-N,N-dimethyl-2-hexenamide
  参考文献：
  名称：

  On the conjugative isomerizations of .beta.,.gamma.-unsaturated esters. Stereochemical generalizations and predictions for 1,3-prototropic shifts under basic conditions

  摘要：

  DOI：

  10.1021/jo00219a020

文献信息

• Direct Carbamoylation of Alkenyl Halides
  作者：Robert F. Cunico、Bikash C. Maity

  DOI：10.1021/ol030110l

  日期：2003.12.1

  Alkenyl chlorides and bromides are converted into tertiary enamides by treatment with a carbamoylsilane in toluene at 110 degrees C in the presence of phosphine-palladium(0) catalysts. [reaction: see text]

  在膦-钯（0）催化剂存在下，通过在甲苯中于110℃下用氨基甲酰基硅烷处理，将链烯基氯化物和溴化物转化为叔酰胺。[反应：看文字]
• Lewis Acid Enabled Copper-Catalyzed Asymmetric Synthesis of Chiral β-Substituted Amides
  作者：Mamen Rodríguez-Fernández、Xingchen Yan、Juan F. Collados、Paul B. White、Syuzanna R. Harutyunyan

  DOI：10.1021/jacs.7b07344

  日期：2017.10.11

  are able to overcome the reactivity issues of unactivated enamides, known as the least reactive carboxylic acid derivatives, toward alkylation with organomagnesium reagents. Allowing unequaled chemo-reactivity and stereocontrol in catalytic asymmetric conjugate addition to enamides, the method is distinguished by its unprecedented reaction scope, allowing even the most challenging and synthetically

  在这里，我们报告说，容易获得的基于甲硅烷基和硼的路易斯酸与手性铜催化剂结合能够克服未活化的烯酰胺（被称为反应性最低的羧酸衍生物）对有机镁试剂进行烷基化的反应性问题。在催化不对称共轭加成到烯酰胺中允许无与伦比的化学反应性和立体控制，该方法以其前所未有的反应范围而著称，即使是最具挑战性和合成上重要的甲基化也能以良好的产率和出色的对映选择性完成。该催化协议可耐受较宽的温度范围（-78 °C 至环境温度）和放大（10 g），而手性催化剂可以重复使用而不会影响整体效率。
• [EN] CYTOTOXIC AND ANTI-MITOTIC COMPOUNDS, AND METHODS OF USING THE SAME<br/>[FR] COMPOSÉS CYTOTOXIQUES ET ANTIMITOTIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：CT FOR DRUG RES AND DEV

  公开号：WO2014144871A1

  公开（公告）日：2014-09-18

  Compounds having cytotoxic and/or anti-mitotic activity are disclosed. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed. Also disclosed are compositions having the structure: (T)-(L)-(D), wherein (T) is a targeting moiety, (L) is an optional linker, and (D) is a compound having cytotoxic and/or anti-mitotic activity.

  揭示了具有细胞毒性和/或抗有丝分裂活性的化合物。还揭示了与制备和使用这些化合物相关的方法，以及包含这些化合物的药物组合物。还揭示了具有结构的组合物：(T)-(L)-(D)，其中(T)是靶向基团，(L)是可选的连接物，(D)是具有细胞毒性和/或抗有丝分裂活性的化合物。
• <i>tert</i>-Butylsulfonamide. A New Nitrogen Source for Catalytic Aminohydroxylation and Aziridination of Olefins
  作者：Alexander V. Gontcharov、Hong Liu、K. Barry Sharpless

  DOI：10.1021/ol990761a

  日期：1999.9.1

  [reaction: see text] The N-chloramine salt of tert-butylsulfonamide has been shown to be an efficient nitrogen source and the terminal oxidant for catalytic aminohydroxylation and aziridination of olefins, resembling closely Chloramine-T by its behavior in these catalytic reactions. The sulfonyl-nitrogen bond in the product or its derivatives is easily cleaved under mild acidic conditions, allowing

  [反应：见正文]叔丁基磺酰胺的N-氯胺盐已被证明是一种有效的氮源和烯烃催化氨基羟基化和叠氮化的末端氧化剂，其在这些催化反应中的行为与Chloramine-T非常相似。产物或其衍生物中的磺酰基-氮键在温和的酸性条件下容易裂解，从而易于释放氨基。
• Synthesis of Cinnamides via Amidation Reaction of Cinnamic Acids with Tetraalkylthiuram Disulfides Under Simple Condition
  作者：Miao Lai、Zhiyong Wu、Fangyao Su、Yujian Yu、Yanqiu Jing、Jinmin Kong、Zhenteng Wang、Shuai Wang、Mingqin Zhao

  DOI：10.1002/ejoc.201901630

  日期：2020.1.16

  A facile and convenient protocol for the synthesis of cinnamides from cinnamic acids and tetraalkylthiuram disulfides under metal and additive free conditions has been achieved. This method allows the efficient coupling of diverse cinnamic acids with tetraalkylthiuram disulfides through a simply mixing operation.

  已经实现了在金属和无添加剂条件下从肉桂酸和四烷基秋兰姆二硫化物合成肉桂酰胺的简便方法。该方法允许通过简单的混合操作将各种肉桂酸与四烷基秋兰姆二硫化物有效偶联。