1,5-bis[(4R)-4-phenyl-3-(2,4,6-trimethoxybenzyl)-1,3-oxazolidin-2-yl]pentane | 301833-44-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,5-bis[(4R)-4-phenyl-3-(2,4,6-trimethoxybenzyl)-1,3-oxazolidin-2-yl]pentane
• 英文别名: (4R)-4-phenyl-2-[3-[(4R)-4-phenyl-3-[(2,4,6-trimethoxyphenyl)methyl]-1,3-oxazolidin-2-yl]propyl]-3-[(2,4,6-trimethoxyphenyl)methyl]-1,3-oxazolidine
• CAS: 301833-44-3
• 化学式: C₄₁H₅₀N₂O₈
• 分子量: 698.857
• InChiKey: RNYIUMAZKFRMBE-CXRHBPHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  51
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,5-bis[(4R)-4-phenyl-3-(2,4,6-trimethoxybenzyl)-1,3-oxazolidin-2-yl]pentane 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (1R,5R)-bis[(R)-N-2-hydroxy-1-phenylethyl]1,5-diphenylpentane-1,5-diamine
  参考文献：
  名称：

  Synthesis of C2-symmetrical chiral diamines: diastereoselective addition to bis(1,3-oxazolidinyl)alkanes with Grignard reagents

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)00268-8
• 作为产物：
  描述：

  环戊烯 、 (R)-N-2,4,6-trimethoxybenzylphenylglycinol 在 臭氧 、 二甲基硫 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以97%的产率得到1,5-bis[(4R)-4-phenyl-3-(2,4,6-trimethoxybenzyl)-1,3-oxazolidin-2-yl]pentane
  参考文献：
  名称：

  Synthesis of C2-symmetrical chiral diamines: diastereoselective addition to bis(1,3-oxazolidinyl)alkanes with Grignard reagents

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)00268-8

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.
• 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.