N-(3-(Trimethylsilyl)-2-propynylidene)aniline | 86936-26-7

• 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-(3-(Trimethylsilyl)-2-propynylidene)aniline
• CAS: 86936-26-7
• 化学式: C₁₂H₁₅NSi
• 分子量: 201.343
• InChiKey: WTNGYCSLMVTUQE-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (三甲基硅基)乙酸甲酯 、 N-(3-(Trimethylsilyl)-2-propynylidene)aniline 在 正丁基锂 、 二异丙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 生成
  参考文献：
  名称：

  Maanen, Hendrik L. van; Kleijn, Henk; Jastrzebski, Johann T. B. H., Recueil des Travaux Chimiques des Pays-Bas, 1994, vol. 113, # 12, p. 567 - 572

  摘要：

  DOI：
• 作为产物：
  描述：

  3-三甲基甲硅烷基丙炔醛 、 苯胺 以93%的产率得到
  参考文献：
  名称：

  BORISOVA, A. I.;DEMINA, M. M.;MEDVEDEVA, A. S.;KALIXMAN, I. D.;VYAZANKIN,+, ZH. OBSHCH. XIMII, 1983, 53, N 6, 1310-1312

  摘要：

  DOI：

文献信息

• Suvorova, I. V.; Stadnichuk, M. D.; Mingaleva, K. S., Journal of general chemistry of the USSR, 1983, vol. 53, # 4, p. 716 - 721
  作者：Suvorova, I. V.、Stadnichuk, M. D.、Mingaleva, K. S.

  DOI：——

  日期：——
• Dualistic Reactivity of Lithium and Zinc Dienolates with Imines: Effects of Counterion, Temperature, and Substituents on .alpha.- and .gamma.-Coupling
  作者：Hendrik L. van Maanen、Henk Kleijn、Johann T. B. H. Jastrzebski、Miles T. Lakin、Anthony L. Spek、Gerard van Koten

  DOI：10.1021/jo00104a048

  日期：1994.12

  Lithium and zinc dienolates of 3-butenoic, 3-methyl-2-butenoic, 3-pentenoic, and 4-phenyl-3-butenoic methyl esters are reacted with imines R(1)C(H)=NR(2)[3a: R(1) = 2-pyridyl, R(2) = Ph; 3b: R(1) = Me(3)-SiC=C; R(2) = Ph; 3c: R(1) = 2-pyridyl, R(2) = (R)-PhCK(CH3); 3d: R(1) = Me(3)SiC=C; R(2) = (R)-PhCH(CH3)]. Depending on metal counterion, temperature, and substituents, the C-C coupling occurs either at the 2-position (alpha-coupling) or at the C-position (gamma-coupling) of the dienolate, giving beta-amino esters and alpha,beta-unsaturated esters, respectively. The alpha-coupling occurs at -78 degrees C and is reversible, whereas gamma-coupling products are formed upon warming to -20 degrees C. The C-C coupled products may undergo irreversible ring closure to beta-lactams (from beta-amino esters) or 5,6-dihydropyridin-2-ones (from Z)-alpha,beta-unsaturated esters). Starting from enantiomerically pure imine 3c, high (71-92%) asymmetric inductions were realized in both beta-lactams and 5,6-dihydropyridin-2-ones; gamma-coupling of enolate 2a and chiral imine 3d occurred with low diastereoselectivity (15%). Four factors favor the formation of beta-lactams: (i) the use of zinc dienolates, (ii) 4-substitution of the dienolates, (iii) nonaromatic imine N-substituents, and (iv) a low reaction temperature (-78 degrees C). The product formation is discussed in terms of six-membered cyclic transition states, involving either zinc enolates (alpha-coupling) or isomeric allylzinc species (gamma-coupling).
• XRAMCHIXIN, A. V.;STADNICHUK, M. D., ZH. OBSHCH. XIMII, 60,(1990) N, S. 609-616
  作者：XRAMCHIXIN, A. V.、STADNICHUK, M. D.

  DOI：——

  日期：——
• CYBOPOBA, I. V.;STADNICHUK, M. D.;MINGALEVA, K. S., ZH. OBSHCH. XIMII, 1983, 53, N 4, 817-823
  作者：CYBOPOBA, I. V.、STADNICHUK, M. D.、MINGALEVA, K. S.

  DOI：——

  日期：——
• CYBOPOBA, I. V.;STADNICHUK, M. D., ZH. OBSHCH. XIMII, 1984, 54, N 1, 132-139
  作者：CYBOPOBA, I. V.、STADNICHUK, M. D.

  DOI：——

  日期：——