(R,E)-dibenzyl 1-(5-ethoxy-5-oxo-1-phenylpent-3-en-2-yl)hydrazine-1,2-dicarboxylate | 935658-81-4

• 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: (R,E)-dibenzyl 1-(5-ethoxy-5-oxo-1-phenylpent-3-en-2-yl)hydrazine-1,2-dicarboxylate
• 英文别名: ethyl (E,4R)-5-phenyl-4-[phenylmethoxycarbonyl(phenylmethoxycarbonylamino)amino]pent-2-enoate
• CAS: 935658-81-4
• 化学式: C₂₉H₃₀N₂O₆
• 分子量: 502.567
• InChiKey: DMWAAJFRVDXBSA-MNUOXJLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R,E)-dibenzyl 1-(5-ethoxy-5-oxo-1-phenylpent-3-en-2-yl)hydrazine-1,2-dicarboxylate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以92%的产率得到(S)-dibenzyl 1-(5-hydroxy-1-phenylpentan-2-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  Proline-Catalyzed Asymmetric Synthesis of syn- and anti-1,3-Diamines

  摘要：

  A general organocatalytic strategy for asymmetric synthesis of both syn/anti-1,3-diamines has been developed. The strategy employs proline-catalyzed sequential alpha-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step where syn-1,3-diamine was obtained as the most favorable product.

  DOI：

  10.1021/jo401722e
• 作为产物：
  描述：

  苯丙醛 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 L-脯氨酸 、 lithium chloride 作用下， 以 乙腈 为溶剂， 生成 (R,E)-dibenzyl 1-(5-ethoxy-5-oxo-1-phenylpent-3-en-2-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  Proline-Catalyzed Asymmetric Synthesis of syn- and anti-1,3-Diamines

  摘要：

  A general organocatalytic strategy for asymmetric synthesis of both syn/anti-1,3-diamines has been developed. The strategy employs proline-catalyzed sequential alpha-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step where syn-1,3-diamine was obtained as the most favorable product.

  DOI：

  10.1021/jo401722e

文献信息

• Organocatalytic Sequential α-Amination−Horner−Wadsworth−Emmons Olefination of Aldehydes:  Enantioselective Synthesis of γ-Amino-α,β-Unsaturated Esters
  作者：Shriram P. Kotkar、Vilas B. Chavan、Arumugam Sudalai

  DOI：10.1021/ol063012j

  日期：2007.3.1

  A novel and highly enantioselective method for the synthesis of gamma-amino-alpha,beta-unsaturated esters via tandem alpha-amination-Horner-Wadsworth-Emmons (HWE) olefination of aldehydes is described. The one-pot assembly has been demonstrated for the construction of functionalized chiral 2-pyrrolidones, subunits present in several alkaloids.
• Proline-Catalyzed Asymmetric Synthesis of <i>syn</i>- and <i>anti</i>-1,3-Diamines
  作者：Pradeep Kumar、Vishwajeet Jha、Rajesh Gonnade

  DOI：10.1021/jo401722e

  日期：2013.12.6

  A general organocatalytic strategy for asymmetric synthesis of both syn/anti-1,3-diamines has been developed. The strategy employs proline-catalyzed sequential alpha-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step where syn-1,3-diamine was obtained as the most favorable product.