spiro[2,5]octane-1,1-dicarboxylic acid dimethyl ester | 68157-22-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: spiro[2,5]octane-1,1-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl spiro[2.5]octane-2,2-dicarboxylate
• CAS: 68157-22-2
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: LIJJAVHZTBTMQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  137 °C(Press: 13 Torr)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  spiro[2,5]octane-1,1-dicarboxylic acid dimethyl ester 在 sodium hydroxide 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 16.0h， 生成 Methyl 2-isocyanatospiro[2.5]octane-2-carboxylate
  参考文献：
  名称：

  Straightforward Synthesis of 1-Amino-2,2-dialkylcyclopropanecarboxylic Acids via Selective Saponification of 2,2-Dialkylcyclopropane-1,1-dicarboxylic Esters and Curtius Rearrangement

  摘要：

  Selective monosaponification of dimethyl 2,2-dialkylcyclopropane-1,1l-dicarboxylic esters afforded the corresponding 2,2-dialkyl-1-(methoxycarbonyl)cyclopropane-1-carboxylic acids, which were rearranged with diphenyl phosphoroazidate via a modified Curtius-type reaction to give methyl 2,2-dialkyl-1-[N-(alkoxycarbonyl)amino]cyclopropanecarboxylic esters. Selective deprotection of the carbamate or methyl cyclopropanecarboxylic ester was worked out, giving rise to a whole variety of ACC analogues. Straightforward ways to 1-amino-2,2-dialkylcyclopropanecarboxylic acids (2,2-dialkyl-ACC's) were developed.

  DOI：

  10.1021/jo00105a045
• 作为产物：
  描述：

  Dimethyl-<1-Brom-cyclohexyl>-methyliden-malonat 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 spiro[2,5]octane-1,1-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Preparation of 2,2-Dialkylcyclopropanes Geminally Substituted with Electron-Withdrawing Groups

  摘要：

  DOI：

  10.1055/s-1978-24799

文献信息

• 一种连三嗪类似物的合成方法
  申请人：兰州大学

  公开号：CN104193692B

  公开（公告）日：2016-09-14

  本发明公开一种连三嗪类似物的合成方法，所述连三嗪类似物的结构式如下：，其中，所述R1为烷基、烯基、芳基或氢；所述R2为烷基、烯基、芳基、呋喃基、吡啶基、吡咯基或氢；所述R3为‑CN、‑NO2或‑COR5，所述R5为烷基、烷氧基或芳基；所述R4为‑CN、‑NO2或‑COR6，所述R6为烷基、烷氧基或芳基；将与混合，在路易斯酸作用下反应得到所述连三嗪类似物。采用本发明可一步环化得到各种取代的连三嗪类似物，产物收率达到80%以上，操作简单。
• A novel method for the sterically shielded pyrrolidine nitroxides synthesis using donor–acceptor cyclopropanes
  作者：Andrey I. Taratayko、Sophia Yu. Trakhinina、Konstantin A. Lomanovich、Igor A. Kirilyuk

  DOI：10.1016/j.tetlet.2023.154546

  日期：2023.6

  shielded nitroxides were shown to demonstrate resistance to bioreduction. For this reason, they are attracting much interest as spin labels and probes for in-cell and in vivo EPR and NMR applications. Formal [3 + 2] cycloaddition reaction of donor–acceptor cyclopropanes with propionitrile provided 1-pyrrolines which were converted to the new sterically shielded achiral pyrrolidine nitroxides via several

  空间屏蔽的氮氧化合物显示出对生物还原的抗性。出于这个原因，它们作为细胞内和体内 EPR 和NMR应用的自旋标记物和探针引起了人们的极大兴趣。供体-受体环丙烷与丙腈的正式 [3 + 2] 环加成反应提供 1-吡咯啉，通过几个步骤将其转化为新的空间屏蔽非手性吡咯烷氮氧化物。
• TiCl₄ Promoted Formal [3 + 3] Cycloaddition of Cyclopropane 1,1-Diesters with Azides: Synthesis of Highly Functionalized Triazinines and Azetidines
  作者：Huan-Huan Zhang、Yong-Chun Luo、Hua-Peng Wang、Wei Chen、Peng-Fei Xu

  DOI：10.1021/ol5024079

  日期：2014.9.19

  A TiCl4 promoted formal [3 + 3] cycloaddition of cyclopropane 1,1-diesters with azides has been developed for the synthesis of highly functionalized triazinines. Both stoichiometric and substoichiometric versions of this reaction were accomplished dependent on the choice of solvent. It is noteworthy that the corresponding products could be easily converted to biologically important azetidines by simple thermolysis.
• Synthesis of Cyclohexanes via [3 + 3] Hexannulation of Cyclopropanes and 2-Chloromethyl Allylsilanes
  作者：Katarina Sapeta、Michael A. Kerr

  DOI：10.1021/ol900457z

  日期：2009.5.21

  Lewis acid-assisted ring-opening/allylation of 1,1-cyclopropane diesters, followed by base-mediated ring closure, generates functionalized exo-methylenecyclohexanes in good yield. This two-step procedure is highlighted by expedient preparation of a pyrido[1,2-a]indole skeleton common to the chippiine class of Iboga indole alkaloids.
• TfOH-Catalyzed Formal [3 + 2] Cycloaddition of Cyclopropane 1,1-Diesters with Nitriles
  作者：Bo Cui、Jun Ren、Zhongwen Wang

  DOI：10.1021/jo402383a

  日期：2014.1.17

  A triflic acid-catalyzed formal [3 + 2] cycloaddition of cyclopropane 1,1-diesters with nitriles was developed. This reaction was expeditious, and the scope of the substituents in both cyclopropanes and nitriles was broad. This supplies an efficient and practical method for the synthesis of 1-pyrrolines.