ethyl 2-diazo-3-o-tolylpropanoate | 1334319-65-1

• 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: ethyl 2-diazo-3-o-tolylpropanoate
• 英文别名: Ethyl 2-diazo-3-(2-methylphenyl)propanoate
• CAS: 1334319-65-1
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: HRDMFDCQUANFRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-diazo-3-o-tolylpropanoate 、 3,4-二氢-1(2H)-萘酮 在 C₄₃H₆₄N₄O₄ 、 lithium carbonate 、 scandium tris(trifluoromethanesulfonate) 作用下， 反应 24.08h， 以93%的产率得到ethyl 2-(2-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)hydrazono)-3-o-tolylpropanoate
  参考文献：
  名称：

  New Electrophilic Addition of α-Diazoesters with Ketones for Enantioselective C–N Bond Formation

  摘要：

  alpha-Diazoesters were discovered to be good electrophiles in a catalytic asymmetric alpha-functionalization of ketones for the first time. This reaction also provided a direct and efficient method for C-N bond formation with excellent yields (up to 98%) and enantioselectivities (up to 99% ee) under mild conditions. The application of the electrophilicity of alpha-diazoesters opens up a novel way to access the diversity of diazo chemistry.

  DOI：

  10.1021/ja2056159

文献信息

• A Catalytic Asymmetric Ring‐Expansion Reaction of Isatins and α‐Alkyl‐α‐Diazoesters: Highly Efficient Synthesis of Functionalized 2‐Quinolone Derivatives
  作者：Wei Li、Xiaohua Liu、Xiaoyu Hao、Yunfei Cai、Lili Lin、Xiaoming Feng

  DOI：10.1002/anie.201204594

  日期：2012.8.20

  Asymmetric expansion: A catalytic asymmetric ring‐expansion reaction of the title compounds occurs in the presence of a Sc(OTf)3 catalyst bearing an N,N′‐dioxide‐based ligand. Highly functionalized 2‐quinolone derivatives containing a chiral C4‐quaternary stereocenter were obtained in high yields and high levels of selectivity under mild reaction conditions (see scheme; Tf=trifluoromethanesulfonyl)

  非对称扩展：标题化合物的催化非对称扩环反应发生在钪（OTF）的存在3催化剂承载有Ñ，Ñ '基于二氧化物-配体。以高产率和温和的反应条件下高水平选择性的得到含有手性C4季立体中心高度官能2-喹诺酮衍生物（参见方案; TF =三氟甲磺酰基）。