rac-2-(N,N-Dibenzylamino)-2,5-dihydro-3-methoxyfuran | 153397-81-0

• 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: rac-2-(N,N-Dibenzylamino)-2,5-dihydro-3-methoxyfuran
• 英文别名: N,N-dibenzyl-1-(3-methoxy-2,5-dihydrofuran-2-yl)methanamine
• CAS: 153397-81-0
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: RTXCVYKOTSVOSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rac-2-(N,N-Dibenzylamino)-2,5-dihydro-3-methoxyfuran 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以45%的产率得到rac-2-<(N,N-Dibenzylamino)methyl>-4,5-dihydro-3(2H)-furanone
  参考文献：
  名称：

  Stereoselective synthesis of 3(2H)-dihydrofuranones by addition of lithiated methoxyallene to chiral aldehydes

  摘要：

  Lithiated methoxyallene 2 adds to chiral aldehydes such as 5-phenylpropanal and N,N-dibenzylated alpha-amino aldehydes 4-8 to give products 9-14 in good yields and with excellent anti-selectivity. The stereochemical outcome of these reactions can be explained by the Felkin-Anh model in a straightforward manner. The crude reaction products can either be transformed to enones by hydrolysis with acid or be converted into 2,5-dihydro-3-methoxyfuran derivatives 19-24 by treatment with potassium tert-butoxide in DMSO. The latter can be hydrolyzed to give 3(2H)-dihydrofuranones 25-29. The diastereoselectivity of the initial addition step is transferred to the dihydrofuran derivative without a major change in the isomer ratio. Compounds derived from alpha-amino aldehydes 5, 6, and 8 are assumed to be enantiomerically pure. Sodium borohydride reductions of and Grignard additions to 3(2H)-dihydrofuranones 27a and 28a demonstrate that these chiral ketones react in a highly diastereoselective manner. In summary, this paper shows that lithiated methoxyallene 2 can serve as a very useful equivalent for alpha,beta-unsaturated acyl anions and 1,3-dipolar synthons in asymmetric synthesis.

  DOI：

  10.1021/jo00080a013
• 作为产物：
  描述：

  2-(二苄基氨基)乙醛 在 正丁基锂 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.58h， 生成 rac-2-(N,N-Dibenzylamino)-2,5-dihydro-3-methoxyfuran
  参考文献：
  名称：

  Stereoselective synthesis of 3(2H)-dihydrofuranones by addition of lithiated methoxyallene to chiral aldehydes

  摘要：

  Lithiated methoxyallene 2 adds to chiral aldehydes such as 5-phenylpropanal and N,N-dibenzylated alpha-amino aldehydes 4-8 to give products 9-14 in good yields and with excellent anti-selectivity. The stereochemical outcome of these reactions can be explained by the Felkin-Anh model in a straightforward manner. The crude reaction products can either be transformed to enones by hydrolysis with acid or be converted into 2,5-dihydro-3-methoxyfuran derivatives 19-24 by treatment with potassium tert-butoxide in DMSO. The latter can be hydrolyzed to give 3(2H)-dihydrofuranones 25-29. The diastereoselectivity of the initial addition step is transferred to the dihydrofuran derivative without a major change in the isomer ratio. Compounds derived from alpha-amino aldehydes 5, 6, and 8 are assumed to be enantiomerically pure. Sodium borohydride reductions of and Grignard additions to 3(2H)-dihydrofuranones 27a and 28a demonstrate that these chiral ketones react in a highly diastereoselective manner. In summary, this paper shows that lithiated methoxyallene 2 can serve as a very useful equivalent for alpha,beta-unsaturated acyl anions and 1,3-dipolar synthons in asymmetric synthesis.

  DOI：

  10.1021/jo00080a013

文献信息

• Stereoselective synthesis of 3(2H)-dihydrofuranones by addition of lithiated methoxyallene to chiral aldehydes
  作者：Stephan Hormuth、Hans Ulrich Reissig

  DOI：10.1021/jo00080a013

  日期：1994.1

  Lithiated methoxyallene 2 adds to chiral aldehydes such as 5-phenylpropanal and N,N-dibenzylated alpha-amino aldehydes 4-8 to give products 9-14 in good yields and with excellent anti-selectivity. The stereochemical outcome of these reactions can be explained by the Felkin-Anh model in a straightforward manner. The crude reaction products can either be transformed to enones by hydrolysis with acid or be converted into 2,5-dihydro-3-methoxyfuran derivatives 19-24 by treatment with potassium tert-butoxide in DMSO. The latter can be hydrolyzed to give 3(2H)-dihydrofuranones 25-29. The diastereoselectivity of the initial addition step is transferred to the dihydrofuran derivative without a major change in the isomer ratio. Compounds derived from alpha-amino aldehydes 5, 6, and 8 are assumed to be enantiomerically pure. Sodium borohydride reductions of and Grignard additions to 3(2H)-dihydrofuranones 27a and 28a demonstrate that these chiral ketones react in a highly diastereoselective manner. In summary, this paper shows that lithiated methoxyallene 2 can serve as a very useful equivalent for alpha,beta-unsaturated acyl anions and 1,3-dipolar synthons in asymmetric synthesis.