(R)-N-2,4,6-trimethoxybenzylphenylglycinol | 204845-22-7

• 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: (R)-N-2,4,6-trimethoxybenzylphenylglycinol
• 英文别名: (R)-2,4,6-trimethoxybenzylphenylglycinol；N-(2,4,6-trimethoxybenzyl)phenylglycinol；(2R)-2-phenyl-2-[(2,4,6-trimethoxyphenyl)methylamino]ethanol
• CAS: 204845-22-7
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: YJHXZGVESAVCFK-INIZCTEOSA-N

物化性质

• 沸点：
  483.0±40.0 °C(predicted)
• 密度：
  1.139±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-N-2,4,6-trimethoxybenzylphenylglycinol 在 双(乙腈)氯化钯(II) 3 A molecular sieve 、 氧气 、 magnesium 、 copper dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 63.0h， 生成 (6R,1'R)-6-[N-(2'-Hydroxy-1'-phenylethyl)-2,4,6-trimethoxybenzylamino]nonan-2-one
  参考文献：
  名称：

  （+）-和（-）-二氢吡啶的不对称合成：手性亚胺或衍生自（R）-苯基甘氨醇的1,3-恶唑烷的非对映选择性加成物，是有机金属试剂的单一原料

  摘要：

  （+）-和（-）-二氢吡啶类对映体对的不对称合成已经完成。我们的策略是基于天然产物的两种对映体的对映结构通过使用具有单一手性源，（ř）-苯基甘氨醇。除存在亚胺或1，3-恶唑烷中间体外，两种途径均通过相似的方法进行。在手性亚胺和1，3-恶唑烷与有机金属试剂的反应中观察到极好的非对映选择性，从而以高化学产率得到手性胺。两种胺的绝对构型是通过将它们各自转化为二氢吡啶而确定的。（+）-和（-）-二氢吡啶吡啶哌啶生物碱的不对称合成分别通过四个步骤完成，总产率分别为6和11，分别为46％和59％。

  DOI：

  10.1039/a905061b
• 作为产物：
  描述：

  2,4,6-三甲氧基苯甲醛 、 D-苯甘氨醇 在 sodium tetrahydroborate 作用下， 生成 (R)-N-2,4,6-trimethoxybenzylphenylglycinol
  参考文献：
  名称：

  Facile Diastereoselective Reactions of Chiral 1,3-Oxazolidines with Grignard Reagents; Asymmetric Syntheses of 2-Substituted and 2,6-Disubstituted Piperidines

  摘要：

  DOI：

  10.3987/com-97-s32

文献信息

• Concise Total Synthesis of (−)-Deoxocuscohygrine and (−)-Dihydrocuscohygrine
  作者：Takayasu Yamauchi、Sachi Hagiwara、Kimio Higashiyama

  DOI：10.1021/jo801700f

  日期：2008.12.19

  GraphicsThe concise enantioselective total synthesis of C(2)-asymmetrical (-)-deoxocuscohygrine and (-)-dihydrocuscohygrine are described. Double-diastereoselective additions of normal Grignard reagent to bis(1.3-oxazolidine) have been deployed to construct chiral diamine fragments as a key step.
• Poerwono, Hadi; Higashiyama, Kimio; Takahashi, Hiroshi, Heterocycles, 1998, vol. 47, # 1, p. 263 - 270
  作者：Poerwono, Hadi、Higashiyama, Kimio、Takahashi, Hiroshi

  DOI：——

  日期：——
• Synthesis of C2-symmetrical chiral diamines: diastereoselective addition to bis(1,3-oxazolidinyl)alkanes with Grignard reagents
  作者：Takayasu Yamauchi、Kimio Higashiyama、Hajime Kubo、Shigeru Ohmiya

  DOI：10.1016/s0957-4166(00)00268-8

  日期：2000.7

  Asymmetric syntheses of C-2-symmetrical chiral 1,4- and 1,5-diamines with stereogenic centers adjacent to the nitrogen atom have been accomplished. Chiral diamines were prepared by diastereoselective alkylations of bisoxazolidine, which was derived from (R)-phenylglycinol. Methyl and phenyl Grignard reagents were employed as alkylating reagents. In addition, tertiary chiral diamines were readily converted to primary diamines in high yield. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of C2-Symmetrical Chiral Aromatic Diamines by Diastereo- selective Addition to Bis(1,3-oxazolidinyl)aromatics with Grignard Reagents
  作者：Takayasu Yamauchi、Kimio Higashiyama、Shigeru Ohmiya

  DOI：10.3987/com-00-9043

  日期：——

  Ct-Symmetrical chiral bis(1,3-oxazolidinyl)aromatics were prepared by the condensation of aromatic dicarbaldehydes (p-benzene, m-benzene, 2,6-pyridine, 2,5-furan and 2,5-thiophene) with (R)-N-2,4, 6-trimethoxybenzyl phenylglycinol (1). Bulky bis(1,3-oxazolidinyl)aromatics underwent diastereoselective addition with Grignard reagents to give new classes of C-2- symmetrical chiral diaminoaromatics in high yield and diastereoselectivity. The absolute configurations of bulky bis(1,3-oxazolidinyl)aromatics (3) and bis(tert-amino)aromatics (10a) were confirmed by X-Ray spectroscopy.
• Stereocontrolled Syntheses of Piperidine Derivatives Using Diastereoselective Reactions of Chiral 1,3-Oxazolidines with Grignard Reagents:  Asymmetric Syntheses of the Pinidine Enantiomers
  作者：Hadi Poerwono、Kimio Higashiyama、Hiroshi Takahashi

  DOI：10.1021/jo971127i

  日期：1998.4.1