methyl 3-iodocyclobutane-1-carboxylate | 2387601-28-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-iodocyclobutane-1-carboxylate
• 英文别名: Methyl 3-iodocyclobutanecarboxylate
• CAS: 2387601-28-5
• 化学式: C₆H₉IO₂
• 分子量: 240.041
• InChiKey: WBLNBSDMAHEUBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-iodocyclobutane-1-carboxylate 在 Siliacat DPP-Pd 作用下， 以 四氢呋喃 为溶剂， 60.0~120.0 ℃ 、800.01 kPa 条件下， 反应 0.15h， 生成
  参考文献：
  名称：

  Synthesis of Electron-Deficient Heteroaromatic 1,3-Substituted Cyclobutyls via Zinc Insertion/Negishi Coupling Sequence under Batch and Automated Flow Conditions

  摘要：

  Synthesis of 1,3-substituted cyclobutyls enabled by zinc insertion into functionalized iodocyclobutyl derivatives followed by Negishi coupling with halo-heteroaromatics is reported. Two distinct sets of conditions were developed; the first involved a two-step batch protocol using activated Rieke zinc, and the second involved a multistep continuous flow process. Both methods showed complementarity and allowed for rapid access to these medicinally relevant motifs, the possibility of scaling up, and automation for library synthesis.

  DOI：

  10.1021/acs.orglett.8b03588
• 作为产物：
  描述：

  3-氧代环丁烷甲酸甲酯 在 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.5h， 生成 methyl 3-iodocyclobutane-1-carboxylate
  参考文献：
  名称：

  Synthesis of Electron-Deficient Heteroaromatic 1,3-Substituted Cyclobutyls via Zinc Insertion/Negishi Coupling Sequence under Batch and Automated Flow Conditions

  摘要：

  Synthesis of 1,3-substituted cyclobutyls enabled by zinc insertion into functionalized iodocyclobutyl derivatives followed by Negishi coupling with halo-heteroaromatics is reported. Two distinct sets of conditions were developed; the first involved a two-step batch protocol using activated Rieke zinc, and the second involved a multistep continuous flow process. Both methods showed complementarity and allowed for rapid access to these medicinally relevant motifs, the possibility of scaling up, and automation for library synthesis.

  DOI：

  10.1021/acs.orglett.8b03588

文献信息

• Copper-catalysed amination of alkyl iodides enabled by halogen-atom transfer
  作者：Bartosz Górski、Anne-Laure Barthelemy、James J. Douglas、Fabio Juliá、Daniele Leonori

  DOI：10.1038/s41929-021-00652-8

  日期：——

  the fact that nucleophilic displacement (SN2) of alkyl halides with nitrogen nucleophiles is one of the first reactions introduced in organic chemistry teaching, its practical utilization is largely limited to unhindered (primary) or activated (α-carbonyl, benzylic) substrates. Here, we demonstrate an alternative amination strategy where alkyl iodides are used as radical precursors instead of electrophiles

  尽管卤代烷与氮亲核试剂的亲核置换 (S N 2) 是有机化学教学中最早引入的反应之一，但其实际应用在很大程度上仅限于不受阻碍的（初级）或活化的（α-羰基、苄基）底物. 在这里，我们展示了一种替代胺化策略，其中烷基碘被用作自由基前体而不是亲电子试剂。使用 α-氨基烷基自由基可以通过卤素原子转移将碘化物有效地转化为相应的烷基自由基，而铜催化在室温下组装sp 3 C-N 键。该过程提供 S N2 样的可编程性以及在几种密集功能化药物的后期功能化中的应用证明了其在制备有价值的N-烷基化药物类似物方面的实用性。
• [EN] THIENOPYRROLE COMPOUNDS<br/>[FR] COMPOSÉS DE THIÉNOPYRROLE
  申请人：GILEAD SCIENCES INC

  公开号：WO2022221642A1

  公开（公告）日：2022-10-20

  The present disclosure relates generally to certain compounds, pharmaceutical compositions comprising said compounds, and methods of making and using said compounds and pharmaceutical compositions. The compounds and compositions provided herein may be used for the treatment or prevention of an autoimmune disease and/or inflammatory condition, including systemic lupus erythematosus and cutaneous lupus erythematosus.

  本公开一般涉及某些化合物、包含所述化合物的药物组合物以及制造和使用所述化合物和药物组合物的方法。本文提供的化合物和组合物可用于治疗或预防自身免疫性疾病和/或炎症，包括系统性红斑狼疮和皮肤红斑狼疮。
• Cu-Catalyzed C(sp³) Amination of Unactivated Secondary Alkyl Iodides Promoted by Diaryliodonium Salts
  作者：Xin-Yang Lv、Ruben Martin

  DOI：10.1021/acs.orglett.3c01216

  日期：2023.5.26

  Herein, we describe the development of a copper-catalyzed C(sp3) amination of unactivated secondary alkyl iodides mediated by diaryliodonium salts. Our protocol is enabled by the intermediacy of aryl radical species that undergo halogen atom transfer prior to interfacing with copper catalysts, thus setting the basis for a C–N bond formation at sp3-hybridized carbons. The method is characterized by

  在此，我们描述了由二芳基碘盐介导的未活化仲烷基碘的铜催化 C(sp 3 ) 胺化反应的发展。我们的协议是通过在与铜催化剂连接之前经历卤素原子转移的芳基自由基物种的中介作用实现的，从而为在 sp 3 -杂化碳上形成 C-N 键奠定了基础。该方法具有反应条件温和、区域选择性好、底物适用范围广等特点。
• WO2020033488A5
  申请人：——

  公开号：WO2020033488A5

  公开（公告）日：2022-08-08
• SUBSTITUTED BENZIMIDAZOLES AS PAD4 INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP3833438A1

  公开（公告）日：2021-06-16