diethyl 2-(4-methoxyphenyl)cyclobutane-1,1-dicarboxylate | 15812-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl 2-(4-methoxyphenyl)cyclobutane-1,1-dicarboxylate
• CAS: 15812-42-7
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: KLHIXTBFGUPEEH-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C (decomp)(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  155-165 °C(Press: 0.5 Torr)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-(4-methoxyphenyl)cyclobutane-1,1-dicarboxylate 在 氢氧化钾 作用下， 生成 dimethyl 2-(4-methoxyphenyl)cyclobutane-1,1-dicarboxylate
  参考文献：
  名称：

  Burger; Zimmerman, Arzneimittel-Forschung/Drug Research, 1966, vol. 16, # 11, p. 1571 - 1572

  摘要：

  DOI：
• 作为产物：
  描述：

  p-methoxycinnamyl alcohol 在 盐酸 作用下， 以 氯仿 为溶剂， 生成 diethyl 2-(4-methoxyphenyl)cyclobutane-1,1-dicarboxylate
  参考文献：
  名称：

  Burger; Zimmerman, Arzneimittel-Forschung/Drug Research, 1966, vol. 16, # 11, p. 1571 - 1572

  摘要：

  DOI：

文献信息

• Ytterbium Triflate Catalyzed Synthesis of Alkoxy-Substituted Donor−Acceptor Cyclobutanes and Their Formal [4 + 2] Cycloaddition with Imines: Stereoselective Synthesis of Piperidines
  作者：Mahmoud M. Abd Rabo Moustafa、Brian L. Pagenkopf

  DOI：10.1021/ol102062t

  日期：2010.11.5

  A new synthesis of 2-alkoxy-1,1-cyclobutane diesters and their first use in dipolar cycloadditions is reported. Both the formation of the donor−acceptor cyclobutanes and their subsequent annulation with in situ formed imines are catalyzed by Yb(OTf)3. Cyclobutanes with carbon donor groups give piperidines with high trans stereoselectivity.

  报道了2-烷氧基-1，1-环丁烷二酯的新合成及其在偶极环加成中的首次使用。Yb（OTf）3催化了供体-受体环丁烷的形成及其随后与原位形成的亚胺的环化反应。具有碳供体基团的环戊二酮使哌啶具有高反式立体选择性。
• Reaction of Donor-Acceptor Cyclobutanes with Indoles: A General Protocol for the Formal Total Synthesis of (±)-Strychnine and the Total Synthesis of (±)-Akuammicine
  作者：Liang-Wen Feng、Hai Ren、Hu Xiong、Pan Wang、Lijia Wang、Yong Tang

  DOI：10.1002/anie.201611734

  日期：2017.3.6

  A ligand‐promoted catalytic [4+2] annulation reaction using indole derivatives and donor‐acceptor (D‐A) cyclobutanes is reported, thus providing an efficient and atom‐economical access to versatile cyclohexa‐fused indolines with excellent levels of diastereoselectivity and a broad substrate scope. In the presence of a chiral SaBOX ligand, excellent enantioselectivity was realized with up to 94 % ee

  据报道，使用吲哚衍生物和供体-受体（D-A）环丁烷进行配体促进的催化[4 + 2]环化反应，因此可以高效，原子经济地获得具有优异非对映选择性和非对映选择性的多环己环二氢吲哚。广泛的底物范围。在手性SaBOX配体的存在下，具有高达94％ee的优异对映选择性。这种新颖的合成方法被用作从同一共同核心支架进行（±）-氨苄青霉素的全合成和（±）-士古宁的正式全合成的通用方案。
• 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。
• Copper Catalyzed Asymmetric [4 + 2] Annulations of D-A Cyclobutanes with Aldehydes
  作者：Jiang-Lin Hu、Li Zhou、Lijia Wang、Zuowei Xie、Yong Tang

  DOI：10.1002/cjoc.201700584

  日期：2018.1

  Copper catalyzed enantioselective [4 + 2] annulations of D‐A cyclobutanes and aldehydes have been developed. In the presence of a side arm modified chiral bisoxazoline (SaBOX) ligand, the [4 + 2] annulations proceeded smoothly with a broad substrate scope. 22 examples were studied, leading to the corresponding products with various functional groups in 41%–99% yields with >99/1 dr and 90%–96% ee. The

  已经开发了铜催化的D‐A环丁烷和醛的对映选择性[4 + 2]环。在存在侧臂修饰的手性双恶唑啉（SaBOX）配体的情况下，[4 + 2]环空在较宽的底物范围内平稳进行。对22个实例进行了研究，得出具有各种官能团的相应产品，其产率> 41/1 dr和90％–96％ee的产率为41％–99％。将所得的带有两个酯基的产物进行单还原，从而使相应的产物具有出色的非对映选择性，而不会损失对映体纯度。