benzyl-veratryliden-amine | 33859-00-6

• 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: benzyl-veratryliden-amine
• 英文别名: Veratrumaldehyd-benzylimin；Benzyl-veratryliden-amin
• CAS: 33859-00-6
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: DFLJPXRIJLPIOX-SFQUDFHCSA-N

物化性质

• 熔点：
  55 °C
• 沸点：
  204-209 °C(Press: 2 Torr)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  30.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzyl-veratryliden-amine 在 氨 、 氢溴酸 、 lithium 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 生成 甲基多巴
  参考文献：
  名称：

  Ojima, Iwao; Shimizu, Nobuko; Qiu, Xiaogang, Bulletin de la Societe Chimique de France, 1987, # 5, p. 649 - 658

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲氧基苄胺 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙腈 为溶剂， 生成 benzyl-veratryliden-amine
  参考文献：
  名称：

  Mechanistic and synthetic aspects of amine oxidations promoted by 3-methyl-5-ethyllumiflavinium perchlorate

  摘要：

  Preparative and kinetic aspects of the chemistry of 3-methyl-5-ethyllumiflavinium perchlorate (1) with primary and secondary amines have been investigated. Reactions of 1 with primary and secondary amines leads to rapid production of modestly stable C4a-adducts. The rates of these processes, determined by stopped-flow kinetic methods, parallel amine nucleophilicities. The C4a-adducts undergo benzylamine promoted elimination reactions to produce N-benzylaldimine products with fates that parallel reactivity profiles expected for E(2)-elimination processes. Finally, flavinium salt 1 serves as a catalyst for oxidations of primary and secondary amines under aerobic conditions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00206-8

文献信息

• Indium-mediated facile synthesis of 3-unsubstituted β-lactams
  作者：Bimal K. Banik、Anjan Ghatak、Frederick F. Becker

  DOI：10.1039/b002833i

  日期：——

  A simple synthesis of 3-unsubstituted β-lactams was achieved through indium-mediated reaction of imines with ethyl bromoacetate.

  通过铟介导的亚胺与溴乙酸乙酯反应，实现了3-未取代β-内酰胺的简单合成。
• Highly Diastereoselective Synthesis of β-Carboxy-γ-lactams and Their Ethyl Esters via Sc(OTf)₃-Catalyzed Imino Mukaiyama-Aldol Type Reaction of 2,5-Bis(trimethylsilyloxy)furan with Imines
  作者：Manat Pohmakotr、Nattawut Yotapan、Patoomratana Tuchinda、Chutima Kuhakarn、Vichai Reutrakul

  DOI：10.1021/jo070533r

  日期：2007.6.1

  Functionalized γ-lactams are found to be crucial intermediates in the synthesis of biologically important natural products. We herein described a highly diastereoselective synthesis of β-carboxy-γ-lactams and their ethyl ester derivatives, in high yields with high diastereomeric ratio, via the Mukaiyama-aldol type reaction of 2,5-bis(trimethysilyloxy)furan with imines, employing Sc(OTf)3 as a catalyst.

  发现功能化的γ-内酰胺是生物重要的天然产物合成中的关键中间体。我们在本文中描述了通过2,5-双（三甲基甲硅烷基氧基）呋喃与亚胺的Mukaiyama-aldol型反应，以高收率和高非对映体比高产率合成β-羧基-γ-内酰胺及其乙酯衍生物的方法。 Sc（OTf）3作为催化剂。
• New approaches to the asymmetric synthesis of non-proteinogenic α-amino acids and dipeptides through chiral β-lactam intermediates
  作者：Iwao Ojima、Hauh-Jyun C. Chen、Xiaogang Qiu

  DOI：10.1016/s0040-4020(01)86038-5

  日期：1988.1

  Novel and effective routes to optically pure aromatic α-amino acids, α-methyl-α-amino acids and their derivatives including dipeptides are developed via homochiral β-lactams which are obtained through asymmetric [2+2] cycloadditions of ketenes to imines.

  经由纯手性β-内酰胺开发了光学上纯净的芳香族α-氨基酸，α-甲基-α-氨基酸及其衍生物（包括二肽）的新颖有效途径，所述β-内酰胺是通过乙烯酮与亚胺的不对称[2 + 2]环加成而获得的。
• Maier, Ludwig; Diel, Peter J., Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 57, # 1/2, p. 57 - 64
  作者：Maier, Ludwig、Diel, Peter J.

  DOI：——

  日期：——
• Steric and electronic effects on the regioselective formation of platinum(II) metallacycles: crystal structure of [PtMe(3-MeC6H3CHNCH2C6H5)(PPh3)]
  作者：Margarita Crespo、Xavier Solans、Mercè Font-Bardía

  DOI：10.1016/0022-328x(96)83109-3

  日期：1996.2

  The reaction of [Pt(2)Me(4)(mu-SMe(2))(2)] (1) with imines 3,4-(OMe)(2)C6H3CH=NCH(2)Ph (2c) and 3-MeC(6)H(6)CH=NCH(2)Ph (2e) yields cyclometallated compounds [PtMe(3,4-(OMe)(2)C6H2CH=NCH(2)Ph)(SMe(2))] (4c) and [PtMe(3-MeC(6)H(3)CH=NCH(2)Ph)(SMe(2))] (4e) arising from selective metallation at the less hindered of the two non-equivalent ortho positions of the aryl ring, followed by loss of methane. These compounds react with PPh(3) to give cyclometallated compounds [PtMe(3,4-(OMe)(2)C6H2CH=NCH(2)Ph)(PPh(3))] (5c) and [PtMe(3-MeC(6)H(3)CH=NC(2)Ph)(PPh(3))] (5e). Imines 2,4,6-(OMe)(3)C6H2CH=NCH(2)Ph (2a), 3,5-(OMe)(2)C6H3CH=NCH(2)Ph (2b) and 2,5-Me(2)C(6)H(3)CH=NCH(2)Ph (2d) coordinate to platinum through the nitrogen atom to yield compounds [PtMe(2)(ArCH=NCH(2)Ph)(SMe(2))] (3) but fail to produce cyclometallated compounds.