(2S,1'S)-2-<1-(N,N-Dibenzylamino)ethyl>-4,5-dihydro-3(2H)-furanone | 134166-38-4

• 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: (2S,1'S)-2-<1-(N,N-Dibenzylamino)ethyl>-4,5-dihydro-3(2H)-furanone
• 英文别名: (2S)-2-[(1S)-1-(dibenzylamino)ethyl]oxolan-3-one
• CAS: 134166-38-4
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: XLHYZVNOUBQUGS-JXFKEZNVSA-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：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,1'S)-2-<1-(N,N-Dibenzylamino)ethyl>-4,5-dihydro-3(2H)-furanone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 (2S,3R,1'S)-2-<1-(N,N-Dibenzylamino)ethyl>tetrahydrofuran-3-ol 、 (2S,3S,1'S)-2-<1-(N,N-Dibenzylamino)ethyl>tetrahydrofuran-3-ol
  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：

  (2S)-2-(N,N-Dibenzylamino)-4-methoxy-4,5-hexadien-3-ol 在 硫酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 (2S,1'S)-2-<1-(N,N-Dibenzylamino)ethyl>-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

文献信息

• First Synthesis of Enantiomerically Pure Primary Helical Spirocycles Based on the Repetitive Addition of Lithiated Methoxyallene to Chiral 3(2H)-Dihydrofuranone Derivatives
  作者：Stephan Hormuth、Wolfgang Schade、Hans-Ulrich Reißig

  DOI：10.1002/jlac.199619961209

  日期：1996.12

  Repetitive additions to chiral 3(2H)-Dihydrofuranones opened a route to the first enantiomerically pure primary helical spirocyclic compounds. Thus, addition of lithiated methoxyallene 2 to furanone 9 provided adduct 10 with excellent diastereoselectivity. Cyclization with potassium tert-butoxide in DMSO followed by acid hydrolysis of the resulting enol ether moiety gave spirocyclic furanone 12 in

  重复添加手性3（2 H）-二氢呋喃酮，开辟了通往首个对映体纯的初级螺旋螺环化合物的途径。因此，向呋喃酮9中加入锂化的甲氧基烯丙基2可以使加合物10具有非对映选择性。用叔丁醇钾在DMSO中环化，然后酸水解所得烯醇醚部分，以非常好的总收率得到螺环呋喃酮12。重复此三步骤序列，将12转换为15。对于接下来的一系列反应，铈化合物为16，而不是2被用作亲核试剂，导致15合理转化为加合物17。通过应用常规方法，该化合物以适中的总产率转化为对映体纯的四环螺化合物19。如本文所述，官能化的螺化合物可作为超分子化学中对映体纯的构建基。