(3S)-N,N,3-三甲基戊烷酰胺 | 398453-86-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (3S)-N,N,3-三甲基戊烷酰胺
• 中文别名: 环丙胺，2-乙基-1-(1-丙烯基)-，(1R，2S)-rel-(9CI)
• 英文名称: (S)-N,N-dimethyl-3-methylpentanamide
• 英文别名: (3S)-N,N,3-trimethylpentanamide
• CAS: 398453-86-6
• 化学式: C₈H₁₇NO
• 分子量: 143.229
• InChiKey: GRQKXQAOEDQPKW-ZETCQYMHSA-N

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：
  0.88
• 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：

  (3S)-N,N,3-三甲基戊烷酰胺 在 lithium aluminium tetrahydride 、 双氧水 作用下， 以 乙醚 、 水 为溶剂， 20.0~130.0 ℃ 、66.66 Pa 条件下， 反应 25.0h， 生成 (S)-3-甲基戊-1-烯
  参考文献：
  名称：

  Silylformylation of Chiral 1-Alkynes, Catalysed by Solvated Rhodium Atoms

  摘要：

  Solvated rhodium atoms, prepared by the metal vapour synthesis technique, promote the silylformylaton reaction of variously substituted alkynes (RRCH)-R-1-C-2(CH2)(n)C equivalent to CH, with catalytic activities comparable with and even higher than more common species such as Rh-4(CO)(12). Z-Silylalkenals are exclusively formed in high yields (60-95%) indicating syn addition both of CO and of the silane (Me2PhSiH) to the triple bond, The chemoselectivity of the process (silylformylation vs. hydrosilylation) is highly affected by the amount of catalyst employed (mmol of Rh species with respect to the alkyne reagent), by the steric requirements of the acetylenic substrates and by the hydrosilane/alkyne molar ratio. When optically active acetylenes are treated in the presence of Me2PhSiH under carbon monoxide pressure, the silylformylation reaction occurs with total retention of stereochemistry of the stereogenic centre, even if it is at the alpha -position of the unsaturated moiety, to afford enantiomerically enriched beta -silylalkenals.

  DOI：

  10.1002/1099-0690(200111)2001:22<4321::aid-ejoc4321>3.0.co;2-t
• 作为产物：
  描述：

  Magnesium, chloro(2-methylbutyl)- 在 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 101.0h， 生成 (3S)-N,N,3-三甲基戊烷酰胺
  参考文献：
  名称：

  Silylformylation of Chiral 1-Alkynes, Catalysed by Solvated Rhodium Atoms

  摘要：

  Solvated rhodium atoms, prepared by the metal vapour synthesis technique, promote the silylformylaton reaction of variously substituted alkynes (RRCH)-R-1-C-2(CH2)(n)C equivalent to CH, with catalytic activities comparable with and even higher than more common species such as Rh-4(CO)(12). Z-Silylalkenals are exclusively formed in high yields (60-95%) indicating syn addition both of CO and of the silane (Me2PhSiH) to the triple bond, The chemoselectivity of the process (silylformylation vs. hydrosilylation) is highly affected by the amount of catalyst employed (mmol of Rh species with respect to the alkyne reagent), by the steric requirements of the acetylenic substrates and by the hydrosilane/alkyne molar ratio. When optically active acetylenes are treated in the presence of Me2PhSiH under carbon monoxide pressure, the silylformylation reaction occurs with total retention of stereochemistry of the stereogenic centre, even if it is at the alpha -position of the unsaturated moiety, to afford enantiomerically enriched beta -silylalkenals.

  DOI：

  10.1002/1099-0690(200111)2001:22<4321::aid-ejoc4321>3.0.co;2-t

文献信息

• 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。
• Stereoselective 1,4-addition of Grignard reagents to α,β-enamides using a combined chiral auxiliary-catalyst approach
  作者：Kallolmay Biswas、Simon Woodward

  DOI：10.1016/j.tetasy.2008.06.017

  日期：2008.7

  A catalyst composed of (R,R)-MeDuphos and CuBr center dot SMe(2) catalyzes the addition of RMgBr (R = Et, C(5)H(11), Ph) to simple enamides (E)-Me(2)NCOCH = CHR(1) (R(1) = Me, C(5)H(11)) in acceptable yields (50-78%), but with poor to modest enantioselectivities (0-74% ee). By changing the enamide acceptor to the (E)-(Aux)N-COCH = CHMe [Aux = from commercial pseudoephedrine, (R,R)-NMeCHMeCHPhOH] a stereochemically enhanced regime Could be attained. Structurally diverse RMgBr (R = C(5)H(11), vinyl, allyl, Ph) underwent 1,4-additions in 57-89% de and 88-93% yield. In one case, the resulting enolate could be trapped with allyl bromide. (C) 2008 Elsevier Ltd. All rights reserved.
• Silylformylation of Chiral 1-Alkynes, Catalysed by Solvated Rhodium Atoms
  作者：Laura Antonella Aronica、Silvia Terreni、Anna Maria Caporusso、Piero Salvadori

  DOI：10.1002/1099-0690(200111)2001:22<4321::aid-ejoc4321>3.0.co;2-t

  日期：2001.11

  Solvated rhodium atoms, prepared by the metal vapour synthesis technique, promote the silylformylaton reaction of variously substituted alkynes (RRCH)-R-1-C-2(CH2)(n)C equivalent to CH, with catalytic activities comparable with and even higher than more common species such as Rh-4(CO)(12). Z-Silylalkenals are exclusively formed in high yields (60-95%) indicating syn addition both of CO and of the silane (Me2PhSiH) to the triple bond, The chemoselectivity of the process (silylformylation vs. hydrosilylation) is highly affected by the amount of catalyst employed (mmol of Rh species with respect to the alkyne reagent), by the steric requirements of the acetylenic substrates and by the hydrosilane/alkyne molar ratio. When optically active acetylenes are treated in the presence of Me2PhSiH under carbon monoxide pressure, the silylformylation reaction occurs with total retention of stereochemistry of the stereogenic centre, even if it is at the alpha -position of the unsaturated moiety, to afford enantiomerically enriched beta -silylalkenals.