ethyl 2-benzyl-2-isocyano-3-phenylpropanoate | 32755-40-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: ethyl 2-benzyl-2-isocyano-3-phenylpropanoate
• CAS: 32755-40-1
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: MOFNYDJZKPRILA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-benzyl-2-isocyano-3-phenylpropanoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 2-Benzyl-2-formylamino-3-phenyl-propionsaeure
  参考文献：
  名称：

  Schoellkopf,U. et al., Chemische Berichte, 1975, vol. 108, p. 1580 - 1592

  摘要：

  DOI：
• 作为产物：
  描述：

  异氰基乙酸乙酯 、 溴甲苯 在 potassium carbonate 、 四正丁基硫酸铵 作用下， 以 乙腈 为溶剂， 生成 ethyl 2-benzyl-2-isocyano-3-phenylpropanoate
  参考文献：
  名称：

  Conformational switching caused by biphenyl substitution at the C^αposition: ethyl 2-benzyl-2-(formylamino)-3-phenylpropionate and ethyl 3-(1,1′-biphenyl-4-yl)-2-(formylamino)-2-(4-phenylbenzyl)propionate

  摘要：

  The title compounds, C19H21NO3 and C31H29NO3, are derivatives of alpha-aminoisobutyric acid, with benzyl and dibenzyl substitution. The pseudo-peptide formed by the N-formyl and ethyl ester substitution at the C-alpha position switches from a trans - trans to a trans - cis configuration as a result of biphenyl substitution. The packing of the compounds is stabilized by N - H...O and C - H...O hydrogen bonds.

  DOI：

  10.1107/s0108270104013150

文献信息

• Palladium-Catalyzed Divergent Imidoylative Cyclization of Multifunctionalized Isocyanides: Tunable Access to Oxazol-5(4<i>H</i>)-ones and Cyclic Ketoimines
  作者：Jian Wang、Ling Zhong、Shi Tang、Yuan Liu、Shumin Ding、Lianjie Li、Haixia Zhao、Chen Chen、Yongjia Shang

  DOI：10.1021/acs.joc.0c00672

  日期：2020.6.5

  Oxazol-5(4H)-one derivatives were obtained exclusively when allyl-2-benzyl(or allyl)-2-isocyanoacetates were used in the reaction with aryl triflates as electrophiles, whereas cyclic ketoimines were generated in the presence of aryl iodides with the allyl ester group remaining unreacted. The reactions proceeded smoothly under mild conditions with a wide functional group tolerance.

  已经开发了钯催化的多官能化异氰酸酯的可调亚氨基化环化反应，以构建各种含亚胺的杂环。当将2--2-苄基（或烯丙基）-2-异氰基乙酸烯丙酯与芳基三氟甲磺酸酯作为亲电试剂反应时，仅获得恶唑-5（4 H）-1衍生物，而在芳基碘化物存在下生成环状酮亚胺。烯丙基酯基团未反应。反应在温和条件下顺利进行，具有宽泛的官能团耐受性。
• Access to 1-amino-3,4-dihydroisoquinolines <i>via</i> palladium-catalyzed C–H bond aminoimidoylation reaction from functionalized isocyanides
  作者：Zhuang Xiong、Panyuan Cai、Yingshuang Mei、Jian Wang

  DOI：10.1039/c9ra09139d

  日期：——

  Efficient access to 1-amino-3,4-dihydroisoquinolines, through palladium-catalyzed intramolecular C–H bond aminoimidoylation of α-benzyl-α-isocyanoacetates, has been developed. Consecutive isocyanide insertion and C–H bond activation were realized with C–N and C–C bonds formation in one step under redox neutral conditions, employing O-benzoyl hydroxylamines as electrophilic amino sources.

  已经开发出通过钯催化的 α-苄基-α-异氰基乙酸酯的分子内 C-H 键氨基亚氨基化来有效获得 1-氨基-3,4-二氢异喹啉。在氧化还原中性条件下，使用O-苯甲酰羟胺作为亲电子氨基源，通过一步形成 C-N 和 C-C 键，实现了连续的异氰化物插入和 C-H 键活化。
• Palladium-Catalyzed Enantioselective C(sp²)–H Imidoylation by Desymmetrization
  作者：Jian Wang、De-Wei Gao、Jinbo Huang、Shi Tang、Zhuang Xiong、Huaanzi Hu、Shu-Li You、Qiang Zhu

  DOI：10.1021/acscatal.7b00731

  日期：2017.6.2

  An efficient palladium-catalyzed enantioselective isocyanide insertion/desymmetrizing C(sp2)–H bond activation reaction allowed by a SPINOL-derived phosphoramidite ligand was developed. 3,4-Dihydroisoquinolines containing C3 quaternary stereogenic centers were obtained in high yields with good enantioselectivity under mild conditions.

  开发了由SPINOL衍生的亚磷酰胺配体实现的有效的钯催化对映体选择性异氰酸酯插入/脱对称C（SP 2）-H键活化反应。在温和条件下，以高收率和良好的对映选择性获得了含有C3季立体异构中心的3,4-二氢异喹啉。
• Synthesis of highly functionalised dibenzylglycine derivatives via the Suzuki–Miyaura coupling reaction
  作者：Sambasivarao Kotha、Manoranjan Behera、Ramanatham Vinod Kumar

  DOI：10.1016/s0960-894x(01)00686-2

  日期：2002.1

  Several alpha,alpha -dibenzylglycine (alpha -benzylphenylalanine) derivatives were prepared by alkylation of the ethyl isocyanoacetate with different benzyl bromide derivatives. Various aryl groups were introduced in the dibenzylglycine moiety via the Suzuki-Miyaura. coupling reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Schoellkopf,U. et al., Angewandte Chemie, 1971, vol. 83, p. 357 - 358
  作者：Schoellkopf,U. et al.

  DOI：——

  日期：——