(S)-(-)-2-(benzylidene-amino)-2-phenylethanol | 153924-60-8

• 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: (S)-(-)-2-(benzylidene-amino)-2-phenylethanol
• 英文别名: (S)-N-benzylidene-α-phenylglycinol
• CAS: 153924-60-8
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: HEOGPWHVRWZHPH-YLQKULKDSA-N

物化性质

• 沸点：
  364.5±35.0 °C(predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-(-)-2-(benzylidene-amino)-2-phenylethanol 在 盐酸 作用下， 以 硝基甲烷 为溶剂， 生成 (S)-4-((S)-2-Hydroxy-1-phenyl-ethylamino)-2-methylene-4-phenyl-butyric acid
  参考文献：
  名称：

  Stereocontrolled preparation of chiral secondary α-methylene γ-lactams by addition of organozinc reagents derived from 2-(bromomethy])acrylates to imines using β-aminoalcohols as chiral auxiliaries.

  摘要：

  Stereocontrolled addition of isolated organozinc reagents 1, prepared from 2-(bromomethyl)acrylates to imines, can be achieved with d.e. approximately 100% using beta-amino alcohols as chiral auxiliaries. High yields of pure R or S secondary alpha-methylene gamma-lactams can be prepared after a three step elimination of the chiral auxiliary (chloration, dehydrochloration of the resulting beta-chloroamine, acid hydrolysis of enamide).

  DOI：

  10.1016/s0957-4166(00)80253-0
• 作为产物：
  描述：

  D-苯甘氨醇 、 苯甲醛 在 magnesium sulfate 作用下， 以100%的产率得到(S)-(-)-2-(benzylidene-amino)-2-phenylethanol
  参考文献：
  名称：

  将甲氧基丙烯的锂或锌衍生物添加到衍生自苯基甘氨醇的恶唑烷中的区域和非对映化学方面

  摘要：

  研究了甲氧基丙烯衍生的锂和锌试剂对恶唑烷的非对映选择性加成。烯丙基碳负离子锂与恶唑烷反应主要提供具有烯醇醚官能团的 β-氨基醇（y-加合物），锌衍生物产生具有烯丙基醚官能团的氨基醇（a-加合物）。

  DOI：

  10.1055/s-2006-948167

文献信息

• Factors influencing the stereoselectivity in the cycloaddition of imino-dienophiles derived from amino ethers, amino alcohols, and amino acid esters
  作者：Paul N. Devine、Michael Reilly、Taeboem Oh

  DOI：10.1016/s0040-4039(00)73790-7

  日期：1993.9

  Imino dienophiles derived from amino ethers, amino alcohols and amino esters undergo Lewis acid promoted cycloaddition with Danishefsky's diene. Cyclic chelation between the imine and oxygen atom increases the stereoselectivity of the reaction.

  衍生自氨基醚，氨基醇和氨基酯的亚氨基二烯亲和剂与Danishefsky的二烯进行路易斯酸促进的环加成反应。亚胺和氧原子之间的环状螯合增加了反应的立体选择性。
• Chiral phosphinyl analogues of 2-C-arylmorpholinols: 2-aryl-3,5-diphenyl-[1,4,2]-oxazaphosphinanes
  作者：Jean-Noël Volle、David Virieux、Matthieu Starck、Jérôme Monbrun、Ludovic Clarion、Jean-Luc Pirat

  DOI：10.1016/j.tetasy.2006.05.003

  日期：2006.5

  (2R,3R,5R)-2-Aryl-3,5-diphenyl-[1,4,2]-oxazaphosphinanes 6, analogues of C-arylmorpholinol 3, were prepared with diastereomeric excess higher than 94%, via a three step sequence: (i) diastereoselective addition-cyclization reaction from methyl hypophosphite and a chiral imine 10, (ii) pallado-catalyzed arylation, and then (iii) a selective inversion of configuration at the phosphorus center. (c) 2006 Elsevier Ltd. All rights reserved.

  (2R,3R,5R)-2-芳基-3,5-二苯基-[1,4,2]-氧化膦杂环 6 是C-芳基吗啉醇 3 的模拟物。通过以下三步工艺制备：(i) 甲基次磷酸酯和手性亚胺 10 的对映选择性加成-环化反应；(ii) 钯催化的芳基化反应；(iii) 选择性地在磷中心翻转构型。该过程的对映体过量率高于94%。©2006 Elsevier Ltd. 保留所有权利。
• α-phenylglycinol as chiral auxiliary in diastereoselective strecker synthesis of α-amino acids
  作者：T.K. Chakraborty、K. Azhar Hussain、G. Venkat Reddy

  DOI：10.1016/0040-4020(95)00523-b

  日期：1995.8

  The high diastereoselectivity achieved in Strecker synthesis using inexpensive α-phenylglycinol as chiral auxiliary and its facile removal by oxidative cleavage make it an ideal choice for the large scale preparations of optically active α-amino acids specially α-arylglycines present abundantly in glycopeptide antibiotics. A number of chiral amino acids are synthesized following this method. Also molecular

  使用廉价的α-苯基甘氨醇作为手性助剂，在Strecker合成中实现了很高的非对映选择性，并且通过氧化裂解可轻松去除，这使其成为大规模制备旋光性α-氨基酸（尤其是糖肽类抗生素中大量存在的α-芳基甘氨酸）的理想选择。按照这种方法可以合成许多手性氨基酸。还进行了分子力学计算以解释观察到的非对映选择。
• Indium-Mediated Asymmetric Barbier-Type Allylation of Aldimines in Alcoholic Solvents:  Synthesis of Optically Active Homoallylic Amines
  作者：Tirayut Vilaivan、Chutima Winotapan、Vorawit Banphavichit、Tetsuro Shinada、Yasufumi Ohfune

  DOI：10.1021/jo0477244

  日期：2005.4.1

  Chiral aldimines derived from phenylglycinol were diastereoselectively allylated with indium powder/allyl bromide in alcoholic solvents. Both aliphatic and aromatic aldimines provided good yield of the desired products with high diastereoselectivity. A racemization-free protocol for removal of the phenylglycinol auxiliary was also developed. The stereochemical assignment of the homoallylic amine was

  将衍生自苯甘醇的手性醛亚胺在酒精溶剂中与铟粉/溴代烯丙基酯非对映选择性地烯丙基化。脂族和芳族醛亚胺都提供了具有高非对映选择性的所需产物的良好产率。还开发了用于消去苯基甘醇辅助剂的无消旋方案。通过NMR光谱对均烯丙基胺进行立体化学分配，并提出了过渡态模型来解释选择性。
• Stereoselective synthesis of β-lactams by condensation of titanium enolates of 2-pyridylthioesters with imines bearing a chiral auxiliary
  作者：Rita Annunziata、Maurizio Benaglia、Mauro Cinquini、Franco Cozzi、Laura Raimondi

  DOI：10.1016/s0040-4039(00)91831-8

  日期：1993.10

  Addition of the titanium enolates of 2-pyridylthioesters to imines featuring easily removable chiral auxiliaries affords β-lactams in a highly stereoselective fashion.

  在具有易于除去的手性助剂的亚胺中加成2-吡啶硫基钛酸酯的烯醇钛化物，可以以高度立体选择性的方式提供β-内酰胺。