diethyl 2-phenylcyclobutane-1,1-dicarboxylate | 874907-09-2

• 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: diethyl 2-phenylcyclobutane-1,1-dicarboxylate
• 英文别名: 2-Phenyl-cyclobutan-dicarbonsaeure-(1,1)-diaethylester
• CAS: 874907-09-2
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: VPKSKKSNMGFLFX-UHFFFAOYSA-N

物化性质

• 沸点：
  341.7±42.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-phenylcyclobutane-1,1-dicarboxylate 在 sodium hydroxide 、 五氯化磷 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 25.5h， 生成
  参考文献：
  名称：

  Synthesis of the four stereoisomers of cyclobutane analogues of phenylalanine in enantiomerically pure form

  摘要：

  All stereoisomers of 1-amino-2-phenylcyclobutanecarboxylic acid-c(4)Phe-have been synthesized and the series c(n)Phe has thus been completed. The use of two different strategies based on a cyclization reaction, starting from ethyl isocyanoacetate and dialkyl malonate, respectively, gave both cis-c(4)Phe and trans-c(4)Phe in racemic form. HPLC resolution of one of the intermediates using a cellulose-derived chiral stationary phase allowed the isolation of the corresponding enantiomerically pure N-protected amino acids, prepared for incorporation into peptides. The relative stereochemistry of enantiopure compounds has been unambiguously assigned. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.015
• 作为产物：
  描述：

  (1,3-二溴丙基)苯 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 diethyl 2-phenylcyclobutane-1,1-dicarboxylate
  参考文献：
  名称：

  Synthesis of the four stereoisomers of cyclobutane analogues of phenylalanine in enantiomerically pure form

  摘要：

  All stereoisomers of 1-amino-2-phenylcyclobutanecarboxylic acid-c(4)Phe-have been synthesized and the series c(n)Phe has thus been completed. The use of two different strategies based on a cyclization reaction, starting from ethyl isocyanoacetate and dialkyl malonate, respectively, gave both cis-c(4)Phe and trans-c(4)Phe in racemic form. HPLC resolution of one of the intermediates using a cellulose-derived chiral stationary phase allowed the isolation of the corresponding enantiomerically pure N-protected amino acids, prepared for incorporation into peptides. The relative stereochemistry of enantiopure compounds has been unambiguously assigned. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.015

文献信息

• Synthesis of Functionalized Tetrahydropyridines by SnCl ₄ ‐Mediated [4+2] Cycloaddition between Donor–Acceptor Cyclobutanes and Nitriles
  作者：David Tong、Jackie Wu、Nathan Bazinski、Donghyun Koo、Naresh Vemula、Brian L. Pagenkopf

  DOI：10.1002/chem.201903833

  日期：2019.12.2

  Cycloadditions of strained carbocycles promoted by Lewis acids are powerful methods to construct heterocyclic frameworks. In fact, the formal [3+2] cycloadditions of donor-acceptor (DA) cyclopropanes with nitriles has seen particular success in synthesis. In this work, we report on the first [4+2] cycloaddition of nitriles with DA cyclobutanes by Lewis acid activation. Tetrahydropyridine derivatives

  路易斯酸促进的应变碳环的环加成是构建杂环骨架的有效方法。实际上，供体-受体（DA）环丙烷与腈的正式[3 + 2]环加成反应在合成中尤为成功。在这项工作中，我们报告了路易斯酸活化作用使腈与DA环丁烷的第一个[4 + 2]环加成反应。从各种芳基活化的环丁烷二酯和脂族或芳族腈中以高达91％的收率获得四氢吡啶衍生物。
• Synthesis of Hexahydropyridazines by [4 + 2] Cycloaddition of Donor–Acceptor Cyclobutanes and <i>cis</i>-Diazenes
  作者：Jackie Wu、Paul Winiarz、Dhwanish Patel、Johanna de Jong、David Tong、Tristan Chidley、Naresh Vemula、Brian L. Pagenkopf

  DOI：10.1021/acs.orglett.0c00896

  日期：2020.4.17

  The GaCl3-catalyzed [4 + 2] cycloaddition between alkoxy- and aryl-activated donor–acceptor cyclobutane diesters and cis-diazene 1a (4-phenyl-1,2,4-triazoline-3,5-dione, PTAD) is disclosed. The reaction provides hexahydropyridazine derivatives as single diastereomers in good to excellent yields in most cases. The structural assignment of the cycloadduct 3b was unambiguously established by single-crystal

  在烷氧基和芳基活化的供体-受体环丁烷二酯与顺式-二氮烯1a（4-苯基-1,2,4-三唑啉-3,5-二酮，PTAD）之间的GaCl 3催化的[4 + 2]环加成反应为披露。在大多数情况下，该反应提供的六氢哒嗪衍生物为单一非对映异构体，收率良好至极佳。通过单晶X射线衍射明确地确定了环加合物3b的结构分配。
• Leveraging Electron Push‐Pull Effect for Catalytic Polymerization and Degradation of a Cyclobutane Monomer System
  作者：Teng Xie、Shu‐Sen Chen、Yang‐Yang Li、Dian‐Feng Chen

  DOI：10.1002/anie.202405408

  日期：2024.7.22

  DFT calculations guide to unveil the electron push-pull effect in reshaping the polymerizability of non-polymerizable cyclobutane to afford densely functionalized all-carbon main-chain polymers, as well as their degradation to afford alkene derivatives. Successful polymerization conditions consist of Lewis acid, Brønsted base, and a C(sp3)-H initiator, while degradation proceeds with catalytic amount

  DFT 计算揭示了电子推拉效应在重塑不可聚合环丁烷的可聚合性以提供密集官能化的全碳主链聚合物方面的作用，以及其降解以提供烯烃衍生物的过程。成功的聚合条件包括路易斯酸、布朗斯台德碱和 C( sp 3 )-H 引发剂，而降解则通过催化量的酸进行。
• Synthesis and SAR of 2-phenyl-1-sulfonylaminocyclopropane carboxylates as ADAMTS-5 (Aggrecanase-2) inhibitors
  作者：Makoto Shiozaki、Hiroto Imai、Katsuya Maeda、Tomoya Miura、Katsutaka Yasue、Akira Suma、Masahiro Yokota、Yosuke Ogoshi、Julia Haas、Andrew M. Fryer、Ellen R. Laird、Nicole M. Littmann、Steven W. Andrews、John A. Josey、Takayuki Mimura、Yuichi Shinozaki、Hiromi Yoshiuchi、Takashi Inaba

  DOI：10.1016/j.bmcl.2009.08.093

  日期：2009.11

  A series of 1-sulfonylaminocyclopropanecarboxylates was synthesized as ADAMTS-5 (Aggrecanase-2) inhibitors. After an intensive investigation of the central cyclopropane core including its absolute stereochemistry and substituents, we found compound 22 with an Agg-2 IC(50) = 7.4 nM, the most potent ADAMTS-5 inhibitor reported so far. (c) 2009 Elsevier Ltd. All rights reserved.