Glutamic acid, 2-methyl-N-(phenylmethylene)-, dimethyl ester | 64298-96-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Glutamic acid, 2-methyl-N-(phenylmethylene)-, dimethyl ester
• 英文别名: DL-Glutamic acid, 2-methyl-N-(phenylmethylene)-, dimethyl ester；dimethyl 2-(benzylideneamino)-2-methylglutarate；dimethyl N-benzylideneglutamate
• CAS: 64298-96-0；109958-84-1
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: FQXGESHJCOHZTL-LFIBNONCSA-N

物化性质

• 沸点：
  90 °C(Press: 6.3e-2 Torr)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.96
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Glutamic acid, 2-methyl-N-(phenylmethylene)-, dimethyl ester 以70%的产率得到
  参考文献：
  名称：

  MKHAIRI A.; HAMELIN J., TETRAHEDRON LETT., 27,(1986) N 37, 4435-4436

  摘要：

  DOI：
• 作为产物：
  描述：

  丙烯酸甲酯（MA） 生成 Glutamic acid, 2-methyl-N-(phenylmethylene)-, dimethyl ester
  参考文献：
  名称：

  YAOZHONG, J.;CHANGYOU, Z.;SHENGDE, W.;DAIMO, C.;YOUAN, M.;GUILAN, L., TETRAHEDRON, 44,(1988) N 17, C. 5343-5353

  摘要：

  DOI：

文献信息

• X=Y–ZH systems as potential 1,3-dipoles. Part 61: Metal exchanged zeolites, silver(I) oxide, Ni(II) and Cu(I) complexes as catalysts for 1,3-dipolar cycloaddition reactions of imines generating proline derivatives
  作者：Ronald Grigg、Daniel M. Cooper、Stephen Holloway、Simon McDonald、Emma Millington、Mohammed A.B. Sarker

  DOI：10.1016/j.tet.2005.06.110

  日期：2005.9

  stereo-selective 1,3-dipolar reactions of imines of α-amino esters, generating polysubstituted prolines, catalysed by silver(I) exchanged zeolites or silver(I) supported on titania, both in combination with DBU, are described. The use of a catalytic amount of silver(I) oxide, Ni(II) complexes and cuprous iodide as catalysts for the cycloaddition reactions are also disclosed.

  α-氨基酯的亚胺的一系列区域和立体选择性1,3-偶极反应，生成银（I）交换沸石或负载在二氧化钛上的银（I）与DBU结合催化的多取代脯氨酸被描述。还公开了使用催化量的氧化银（I），Ni（II）络合物和碘化亚铜作为环加成反应的催化剂。
• Generation of an<i>N</i>-Sodioazomethine Ylide and Its Cycloadditions with α,β-Unsaturated Esters
  作者：Shuji Kanemasa、Manabu Yoshioka、Otohiko Tsuge

  DOI：10.1246/bcsj.62.2196

  日期：1989.7

  Treatment of methyl 2-(benzylideneamino)propanoate with sodium hydride in THF generates an N-sodioazomethine ylide, which shows a very poor stereoselectivity in the cycloaddition with methyl acrylate. However, addition of such a base as triethylamine or t-butyl alcohol improves the selectivity. Chemical properties of the ylide have been discussed on the basis of the selectivity totally different from that of N-lithio analogue.

  将甲基2-(苄亚氨基)丙酸酯与钠氢化物在四氢呋喃中反应，会生成N-钠偶氮亚胺亚胺，后者在与甲基丙烯酸酯的环加成反应中表现出很差的立体选择性。然而，加入三乙胺或叔丁醇等碱性添加剂可以提高选择性。关于这种亚胺的化学性质已经根据其选择性进行讨论，该选择性与N-锂类同分异构体截然不同。
• X-Y-ZH Systems as potential 1,3-dipoles
  作者：Darrin A. Barr、Ronald Grigg、H.Q.Nimal Gunaratne、James Kemp、Peter McMeekin、Visuvanathar Sridharan

  DOI：10.1016/s0040-4020(01)85844-0

  日期：1988.1

  solvents (MeCN, DMSO, DMF) or N-methylacetamide effects regio- and stereo-specific or highly stereo-selective inter- and intra-molecular cycloaddition of imines of phenylglycine. alanine and glycine esters to a range of dipolarophiles probably via metallo-1,3-dipole formation at room temperature. Silver acetate is a more efficient and selective catalyst than lithium bromide and reactions in acetonitrile

  丙胺和苯甘氨酸酯的芳基亚胺亚胺被叔胺和吡啶脱质子的动力学研究以及所得的4π-氮杂烯丙基阴离子与N-苯基马来酰亚胺的环加成反应表明，预期的依赖于芳环中的对位取代基。例如p-NO 2 > H> OMe> fs NMe 2。THF中的金属盐（银，锂或锌）和三乙胺，偶极非质子传递溶剂（MeCN，DMSO，DMF）或N-甲基乙酰胺的组合可影响区域和立体选择性或高度立体选择性的分子间和分子内苯甘氨酸亚胺的环加成。丙氨酸和甘氨酸酯可能在室温下通过成金属的1，，3-偶极子形成一系列偶极子。乙酸银比溴化锂是一种更有效和更具选择性的催化剂，在乙腈，DMSO或N-甲基乙酰胺中的反应特别快（O.1-3.5h）。
• 5-Endo-trig cyclisation and 1,3-anionic cycloaddition in arylimine derivatives of α-amino acid esters
  作者：Ronald Grigg、James Kemp、John Malone、Anant Tangthongkum

  DOI：10.1039/c39800000648

  日期：——

  Michael adducts of imines of α-amino acid esters are converted into a mixture of two stereoisomeric pyrrolidines by benzyltrimethylammonium methoxide (BTAM) apparently by a 5-endo-trig cyclisation.

  的亚胺的迈克尔加成物α -氨基羧酸酯是显然是由5-转换成苄基三甲基甲醇（BTAM）两种立体异构的吡咯烷的混合物中的内切trig的环化。
• Cycloaddition vs. Michael Addition in the Metal Halide/Amine-Induced Reactions of α-(Alkylideneamino) Esters with Electron-Deficient Olefins
  作者：Shuji Kanemasa、Manabu Yoshioka、Otohiko Tsuge

  DOI：10.1246/bcsj.62.869

  日期：1989.3

  The lithiated intermediate derived from methyl 2-(benzylideneamino)propanoate and lithium bromide/triethylamine undergoes cycloaddition and Michael addition with methyl acrylate. 1,3-Dipole character of the intermediate is suggested on the basis of the product ratios obtained under a variety of conditions. The reaction mechanism via a four-centered transition state is proposed.

  衍生自 2-(亚苄基氨基)丙酸甲酯和溴化锂/三乙胺的锂化中间体与丙烯酸甲酯发生环加成和迈克尔加成。中间体的 1,3-偶极特性是根据在各种条件下获得的产物比率得出的。提出了通过四中心过渡态的反应机制。