2,2-dimethylpropyl diazomethanesulfonate | 120263-45-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2,2-dimethylpropyl diazomethanesulfonate
• 英文别名: neopentyl diazomethanesulfonate；neopentyl α-diazomethanesulfonate；DAMS
• CAS: 120263-45-8
• 化学式: C₆H₁₂N₂O₃S
• 分子量: 192.239
• InChiKey: JJYKXGLIPPECBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  53.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-dimethylpropyl diazomethanesulfonate 在 呋喃 、 dirhodium tetraacetate 作用下， 反应 2.0h， 以95%的产率得到dineopentyl (E)-ethene-1,2-disulfonate
  参考文献：
  名称：

  Exploring the metal-catalyzed reaction of furans with alkyl α-diazomethanesulfonate and α-diazomethanephosphonate: synthesis of ω-acyl-substituted sulfono- and phosphonobutadienes

  摘要：

  The metal-catalyzed reactions of neopentyl or,-diazomethanesulfonate (DAMS) and diisopropyl alpha-diazomethanephosphonate (DIDAMP) with furan, 2-methylfuran and 2-methoxyfuran are reported. The products consist mostly of omega-acyl-substituted sulfono- or phosphonobutadienes and exo-cyclopropane derivatives. Treatment of the multicomponent reaction mixtures with iodine afforded exclusively the corresponding (E,E)-sulfono- and phosphono-omega-acylfunctionalized dienes, thus providing a short and efficient synthetic route to these hitherto unreported classes of compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.040
• 作为产物：
  描述：

  2,2-二甲基丙基甲烷磺酸酯 在 4-乙酰氨基苯磺酰叠氮 、 水 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.67h， 生成 2,2-dimethylpropyl diazomethanesulfonate
  参考文献：
  名称：

  Enantiocontrol in intermolecular cyclopropanations: use of diazosulfonate esters

  摘要：

  研究了α-二磺酸酯作为替代二氮烷酸酯的循环丙烯化试剂的新颖应用。探讨了底物和配体的结构对二叠体选择性和对映选择性的影响，并比较了不同金属的催化能力。

  DOI：

  10.1039/b412285b

文献信息

• Synthesis, Molecular Modeling Studies, and Preliminary Pharmacological Characterization of All Possible 2-(2‘-Sulfonocyclopropyl)glycine Stereoisomers as Conformationally Constrained <i>L</i>-Homocysteic Acid Analogs
  作者：Roberto Pellicciari、Maura Marinozzi、Antonio Macchiarulo、Maria Carmela Fulco、Julia Gafarova、Michaela Serpi、Gianluca Giorgi、Søren Nielsen、Christian Thomsen

  DOI：10.1021/jm070322e

  日期：2007.9.1

  receptors. As a continuation of our work in the preparation of conformationally constrained glutamate analogs, we report the synthesis and the preliminary pharmacological characterization at iGluRs and mGluRs of all eight stereoisomers of 2-(2'-sulfonocyclopropyl)glycine (SCGs, 8-15). Among the reported compounds, S-SCG-4 (15) showed to be a potent and relatively selective AMPA ligand. Docking experiments

  L-谷氨酸的远端酸性基团（L-Glu，1）的生物立体置换和其碳骨架的构象约束已被广泛用于发现竞争性的谷氨酸受体调节剂。值得注意的是，L-高半胱氨酸（L-HCA，18）是一种属于兴奋性含硫氨基酸的神经递质，可以认为是L-Glu的内源性生物等排体（1）。据报道，L-HCA（18）通过激活谷氨酸受体和其他迄今尚未被很好表征的受体来介导神经胶质细胞和突触后神经元之间的信号传导。作为制备构象受限的谷氨酸类似物的工作的延续，我们报告了2-（2''的所有八个立体异构体在iGluRs和mGluRs上的合成和初步药理学表征 -磺酰基环丙基）甘氨酸（SCG，8-15）。在已报道的化合物中，S-SCG-4（15）显示为有效且相对选择性的AMPA配体。通过对接实验与分子静电势计算相结合，可以深入了解该化合物活性的分子基础。SCG库（8-15）在提供谷氨酸受体调节剂的新来源的同时，代表了一种有价值的化学工具，可以更好地表征CNS中的L-HCA途径。
• Synthesis and chromatographic resolution of conformationally constrained analogues of homotaurine
  作者：Maria Carmela Fulco、Maura Marinozzi、Burcu Çaliskan Ergün、Roccaldo Sardella、Benedetto Natalini、Roberto Pellicciari

  DOI：10.1016/j.tet.2009.08.018

  日期：2009.10

  The first series of conformationally constrained analogues of homotaurine is reported. The partial constriction of the skeleton was realized through the insertion of a cyclopropyl ring, between the α,β- and β,γ-positions, thus affording, respectively, trans- and cis-2-aminomethylcyclopropane-1-sulfonic acids and trans- and cis-(2-aminocyclopropyl)methanesulfonic acids. The resolution of all four racemic

  据报道，第一个系列的高牛磺酸构象受限类似物。骨架的局部收缩通过一个环丙基环的插入实现之间的α，β-和β，γ位，由此提供分别反式-和顺-2-氨基甲基环丙烷-1-磺酸和反式-与顺式- （2-氨基环丙基）甲磺酸。所有四个外消旋混合物的分辨率使用HPLC系统携带基于多糖的CHIRALPAK完成® IB ®列作为手性固定相。在色谱研究期间，与“蒸发光散射检测器（ELSD）”的结合特别有价值。
• BERKESSEL, ALBRECHT;VOGES, MARKUS, CHEM. BER., 122,(1989) N, C. 1147-1151
  作者：BERKESSEL, ALBRECHT、VOGES, MARKUS

  DOI：——

  日期：——
• Enantiocontrol in intermolecular cyclopropanations: use of diazosulfonate esters
  作者：Tao Ye、Congying Zhou

  DOI：10.1039/b412285b

  日期：——

  The novel use of α-diazosulfonate esters as alternative cyclopropanating agents to diazoacetates is investigated. The effects of structure of both substrate and ligand on diastereo- and enantioselectivity are studied, and the catalytic ability of different metals is compared.

  研究了α-二磺酸酯作为替代二氮烷酸酯的循环丙烯化试剂的新颖应用。探讨了底物和配体的结构对二叠体选择性和对映选择性的影响，并比较了不同金属的催化能力。
• Exploring the metal-catalyzed reaction of furans with alkyl α-diazomethanesulfonate and α-diazomethanephosphonate: synthesis of ω-acyl-substituted sulfono- and phosphonobutadienes
  作者：Maura Marinozzi、Maria Carmela Fulco、Laura Amori、Massimiliana Fiumi、Roberto Pellicciari

  DOI：10.1016/j.tet.2009.06.040

  日期：2009.8

  The metal-catalyzed reactions of neopentyl or,-diazomethanesulfonate (DAMS) and diisopropyl alpha-diazomethanephosphonate (DIDAMP) with furan, 2-methylfuran and 2-methoxyfuran are reported. The products consist mostly of omega-acyl-substituted sulfono- or phosphonobutadienes and exo-cyclopropane derivatives. Treatment of the multicomponent reaction mixtures with iodine afforded exclusively the corresponding (E,E)-sulfono- and phosphono-omega-acylfunctionalized dienes, thus providing a short and efficient synthetic route to these hitherto unreported classes of compounds. (C) 2009 Elsevier Ltd. All rights reserved.