Benzylideneamine | 123016-86-4

• 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: Benzylideneamine
• 英文别名: (E)-N-[bis(trimethylsilyl)methyl]-1-phenylmethanimine
• CAS: 123016-86-4
• 化学式: C₁₄H₂₅NSi₂
• 分子量: 263.53
• InChiKey: IVNKBXWUJJTCLW-NTCAYCPXSA-N

物化性质

• 沸点：
  285.0±30.0 °C(Predicted)
• 密度：
  0.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Benzylideneamine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 C14H27NSi2
  参考文献：
  名称：

  Fluoride ion mediated peterson alkenation of N-[C,C-bis(trimethylsilyl)methyl]amido derivatives with carbonyl compounds: a short general route to enamides and 1,2-dihydroisoquinolines.

  摘要：

  A straightforward general access to diversely substituted acyclic or cyclic enamides and dienamides is accomplished by using a fluoride induced Peterson olefination of carbonyl compounds and enolizable amides derived from C,C-bis(trimethylsilyl) methylamine.

  DOI：

  10.1016/s0040-4039(00)74815-5
• 作为产物：
  描述：

  azidobis(trimethylsilyl)methane 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.33h， 生成 Benzylideneamine
  参考文献：
  名称：

  Synthesis and Reactivity of N-[Bis(trimethylsilyl)methyl]heterocumulenes

  摘要：

  A number of N-heterocumulenes bearing the (Me(3)Si)(2)CH (BSM) substituent adjacent to the terminal nitrogen atom of the heterocumulene function, namely BSM-N=C=O (2), BSM-N=C=S (3), BSM-N=C=NR(4: R = BSM; 5: R = C6H5), BSM-N=C=CR(1)R(2) (9a: R(1) = R(2) = C6H5; 9b: R(1) = H, R(2) = SiMe(3); 10: R(1) = R(2) = CH3; 12: R(1) = H; R(2) = CH3), and BSM-N=S=O (14), have been synthesized. The synthetic utility of the BSM-N-substituted heterocumulenes has been explored through the creation of a carbanion center at the a position relative to nitrogen. In particular, the following reactions have been studied: (i) the nucleophilic addition of MeLi to compounds 2 and 5, (ii) the MeLi-induced deprotonation of ketene imines 9a,b (this investigation includes the study of the regiochemical output of the addition of electrophiles (H2O, Mel, Me(2)CHI) to the resulting 1,3-dipoles; and (iii) the TBAF-induced desilylation of compounds 2 and 9a followed by reaction with benzaldehyde.

  DOI：

  10.1021/jo00124a011

文献信息

• Fluoride ion mediated peterson alkenation of bis(trimethylsilyl)methylimines: a novel synthesis of 2-aza-1,3-dienes and N-vinyl-β-lactams
  作者：Juan Lasarte、Claudio Palomo、Jean P. Picard、Jacques Dunogues、Jesús M. Aizpurua

  DOI：10.1039/c39890000072

  日期：——

  The formation of bis(trimethylsily)methylimines and their transformation into aza-1,3-dienes by means of a fluoride-induced catalytic Peterson alkenation is reported; when the procedure was applied to N-[bis(trimethylsilyl)methyl]-azetidin-2-ones, a wide range of N-vinyl derivatives were obtained in high yields.

  据报道，双（三甲基甲硅烷基）甲基亚胺的形成及其通过氟化物催化的彼得森烯化反应转变成氮杂1,3-二烯；当将该方法用于N- [双（三甲基甲硅烷基）甲基]-氮杂环丁烷-2-酮时，可以高收率获得各种N-乙烯基衍生物。
• A Contribution to the Asymmetric Synthesis of 3-Amino β-Lactams: The Diastereoselective [2+2] Cycloaddition Reaction of Chiral Aminoketene Equivalents with Enolizable Aldehyde-Derived Imines
  作者：Claudio Palomo、Jesus M. Aizpurua、Marta Legido、Antonia Mielgo、Regina Galarza

  DOI：10.1002/chem.19970030909

  日期：1997.9

  AbstractN‐[Bis(trimethylsilyl)methyl]imines 9 show unique chemical properties when compared with conventional imines. Their reaction with optically pure aminoketenes derived from dehydrochlorination of 14 and 15 affords the corresponding 3‐amino‐4‐alkyl‐β‐lactams 16 and 17 in good yields and high diastereoselectivities. The mild deprotection of bis(trimethylsilyl)methyl‐ and phenyloxazolidinone moieties with, respectively, cerium(IV) ammonium nitrate and lithium/ammonia or hydrogen/Pd(OH)2 allows the preparation of a variety of β‐lactam antibiotic building blocks.
• LASARTE, JUAN;PALOMO, CLAUDIO;PICARD, JEAN P.;DUNOGUES, JACQUES;AIZPURUA,+, J. CHEM. SOC. CHEM. COMMUN.,(1989) N, C. 72-74
  作者：LASARTE, JUAN、PALOMO, CLAUDIO、PICARD, JEAN P.、DUNOGUES, JACQUES、AIZPURUA,+

  DOI：——

  日期：——
• Synthesis and Reactivity of N-[Bis(trimethylsilyl)methyl]heterocumulenes
  作者：Gaetano Barbaro、Arturo Battaglia、Patrizia Giorgianni、Andrea Guerrini、Giancarlo Seconi

  DOI：10.1021/jo00124a011

  日期：1995.9

  A number of N-heterocumulenes bearing the (Me(3)Si)(2)CH (BSM) substituent adjacent to the terminal nitrogen atom of the heterocumulene function, namely BSM-N=C=O (2), BSM-N=C=S (3), BSM-N=C=NR(4: R = BSM; 5: R = C6H5), BSM-N=C=CR(1)R(2) (9a: R(1) = R(2) = C6H5; 9b: R(1) = H, R(2) = SiMe(3); 10: R(1) = R(2) = CH3; 12: R(1) = H; R(2) = CH3), and BSM-N=S=O (14), have been synthesized. The synthetic utility of the BSM-N-substituted heterocumulenes has been explored through the creation of a carbanion center at the a position relative to nitrogen. In particular, the following reactions have been studied: (i) the nucleophilic addition of MeLi to compounds 2 and 5, (ii) the MeLi-induced deprotonation of ketene imines 9a,b (this investigation includes the study of the regiochemical output of the addition of electrophiles (H2O, Mel, Me(2)CHI) to the resulting 1,3-dipoles; and (iii) the TBAF-induced desilylation of compounds 2 and 9a followed by reaction with benzaldehyde.
• Fluoride ion mediated peterson alkenation of N-[C,C-bis(trimethylsilyl)methyl]amido derivatives with carbonyl compounds: a short general route to enamides and 1,2-dihydroisoquinolines.
  作者：Claudio Palomo、Jesús M. Aizpurua、Marta Legido、Jean Paul Picard、Jacques Dunogues、Thierry Constantieux

  DOI：10.1016/s0040-4039(00)74815-5

  日期：1992.6

  A straightforward general access to diversely substituted acyclic or cyclic enamides and dienamides is accomplished by using a fluoride induced Peterson olefination of carbonyl compounds and enolizable amides derived from C,C-bis(trimethylsilyl) methylamine.