2-diazo-pent-4-ynoic acid ethyl ester | 1029092-22-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 2-diazo-pent-4-ynoic acid ethyl ester
• 英文别名: ethyl 2-diazopent-4-ynoate；ethyl α-propargyldiazoacetate
• CAS: 1029092-22-5
• 化学式: C₇H₈N₂O₂
• 分子量: 152.153
• InChiKey: SQDAYQOPYLNSTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  2-diazo-pent-4-ynoic acid ethyl ester 、 3,4-二氢-1(2H)-萘酮 在 C₄₅H₆₈N₄O₄ 、 lithium carbonate 、 scandium tris(trifluoromethanesulfonate) 作用下， 反应 26.08h， 生成 ethyl 2-(2-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)hydrazono)pent-4-ynoate
  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
• 作为产物：
  描述：

  ethyl 2-acetylpent-4-ynoate 在 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 2-diazo-pent-4-ynoic acid ethyl ester
  参考文献：
  名称：

  对映选择性合成α-烷基-β-酮酸酯：恶唑硼烷鎓离子催化的不对称Roskamp反应

  摘要：

  破坎普：朝向用α -烷基diazoester与醛标题反应已经开发手性α-烷基-β酮酯的催化路线（参见方案）。该反应具有高至优异的对映选择性，这方法适用于天然信息素sitophilate一个简明的两步合成。

  DOI：

  10.1002/anie.201204350

文献信息

• Direct ionic liquid promoted organocatalyzed diazo-transfer reactions: diversity-oriented synthesis of diazo-compounds
  作者：Dhevalapally B. Ramachary、Vidadala V. Narayana、Kinthada Ramakumar

  DOI：10.1016/j.tetlet.2008.02.159

  日期：2008.4

  A practical and novel ionic liquid promoted organocatalytic selective diazo-transfer process for the synthesis of highly substituted diazo-compounds in high yields is reported. The ionic liquid can be reused without affecting the reaction rates or yields over five runs.

  报道了一种实用且新颖的离子液体促进的有机催化选择性重氮转移工艺，用于高收率地合成高度取代的重氮化合物。可以重复使用该离子液体，而不会影响五次运行的反应速率或产率。
• Synthesis of 1,3-dioxo-substituted allenes via copper(I)-catalyzed coupling of α-oxo-alkynes and α-oxo-diazos by controlling the sequence of adding substrates
  作者：Chulong Liu、Yunxiang Weng、Xiaobao Zeng、Weiping Zheng、Xinyan Wang、Yuefei Hu

  DOI：10.1016/j.tetlet.2019.01.015

  日期：2019.2

  A novel direct synthesis of 1,3-dioxo-substituted allenes was developed by copper(I)-catalyzed coupling of α-oxo-alkynes and α-oxo-diazos. It was a sequence of adding substrates-controlled method and the desired products were synthesized chemoselectively by adding α-oxo-alkyne terminally.

  通过铜（I）催化α-氧代炔烃和α-氧代重氮偶合的偶联反应，开发了一种新的直接合成1,3-二氧代取代的丙二烯的方法。这是添加底物控制方法的顺序，并且通过末端添加α-氧代炔烃来化学选择性地合成所需的产物。
• Iron catalyzed efficient synthesis of poly-functional primary amines via the direct use of ammonia
  作者：Chaoqun Ma、Jianghui Chen、Dong Xing、Yuan Sheng、Wenhao Hu

  DOI：10.1039/c7cc00003k

  日期：——

  An iron catalyzed three-component reaction of alkyl diazoesters, isatins and ammonia is reported. This reaction provided convenient access to non-protected [small beta]-hydroxy-[small alpha]-aminoesters with adjacent quaternary stereocenters. This transformation is achieved via...

  报道了铁催化的烷基重氮酯，靛红和氨的三组分反应。该反应提供了获得具有相邻的季立体中心的未保护的β-羟基-α-氨基小酯的便利途径。这种转变是通过...
• 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）。