ethyl 2-diazo-3-m-tolylpropanoate | 859190-29-7

• 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-m-tolylpropanoate
• CAS: 859190-29-7
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: CPJZYAIBGRQZGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.7
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-diazo-3-m-tolylpropanoate 、 3,4-二氢-1(2H)-萘酮 在 C₄₅H₆₈N₄O₄ 、 lithium carbonate 、 scandium tris(trifluoromethanesulfonate) 作用下， 反应 24.08h， 生成 ethyl 2-(2-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)hydrazono)-3-m-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）。
• Visible-Light-Induced Catalysis: A Regioselectivity Switch between [2+1] and [2+2] Cycloaddition of Diazocarbonyls with Olefins
  作者：Jian Lv、Huixin Qiu、Lirong Wen

  DOI：10.1055/a-1786-6496

  日期：2022.9

  Visible-light-promoted [2+1] and [2+2] cycloaddition reactions of diazocarbonyls with olefins have been developed, affording functionalized cyclopropanes and cyclobutanes, respectively. In visible-light catalysis of Ir(ppy)3, a simple addition of Rh2(OAc)4 switches the regioselectivity from [2+1] to [2+2] cycloaddition with good reactivity and high regioselectivity.

  已经开发了重氮羰基与烯烃的可见光促进的 [2+1] 和 [2+2] 环加成反应，分别得到官能化的环丙烷和环丁烷。在 Ir(ppy) 3的可见光催化中，Rh 2 (OAc) 4的简单添加将区域选择性从 [2+1] 转变为 [2+2] 环加成，具有良好的反应性和高区域选择性。