N',N-bis(ethoxycarbonyl)-3-hydrazino-4-phenyl-2-butanone

• 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: N',N-bis(ethoxycarbonyl)-3-hydrazino-4-phenyl-2-butanone
• 英文别名: ethyl N-(ethoxycarbonylamino)-N-[(2R)-3-oxo-1-phenylbutan-2-yl]carbamate
• 化学式: C₁₆H₂₂N₂O₅
• 分子量: 322.361
• InChiKey: RVNGCJRPTLUAPI-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲基溴化镁 、 N',N-bis(ethoxycarbonyl)-3-hydrazino-4-phenyl-2-butanone 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 3.25h， 以71%的产率得到
  参考文献：
  名称：

  Asymmetric synthesis of vicinal amino alcohols via organocatalytic sequential α-amination/Grignard addition reactions of aldehydes

  摘要：

  An organocatalytic sequential alpha-amination/Grignard addition reaction of aliphatic aldehydes is reported. The synthetically useful anti-vicinal amino alcohol derivatives were obtained in high yields and with high stereoselectivities. These derivatives could be easily transformed into oxazolidinones. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.12.004
• 作为产物：
  描述：

  苄基丙酮 、 偶氮二甲酸二乙酯 在 L-脯氨酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以98%的产率得到
  参考文献：
  名称：

  Asymmetric synthesis of vicinal amino alcohols via organocatalytic sequential α-amination/Grignard addition reactions of aldehydes

  摘要：

  An organocatalytic sequential alpha-amination/Grignard addition reaction of aliphatic aldehydes is reported. The synthetically useful anti-vicinal amino alcohol derivatives were obtained in high yields and with high stereoselectivities. These derivatives could be easily transformed into oxazolidinones. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.12.004

文献信息

• Direct <scp>l</scp>-Proline-Catalyzed Asymmetric α-Amination of Ketones
  作者：Nagaswamy Kumaragurubaran、Karsten Juhl、Wei Zhuang、Anders Bøgevig、Karl Anker Jørgensen

  DOI：10.1021/ja026412k

  日期：2002.6.1

  The first direct catalytic asymmetric alpha-amination of ketones catalyzed by l-proline has been developed. The reactions proceed with various azodicarboxylates as the nitrogen source in high yields and excellent enantioselectivities (up to 99% ee). The scope and potential of the reaction are demonstrated by further transformation of the alpha-hydrazino ketones formed to both optically active syn and anti-alpha-amino alcohol derivatives.