1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-nitroethanol | 689276-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-nitroethanol
• CAS: 689276-87-7
• 化学式: C₇H₁₃NO₅
• 分子量: 191.184
• InChiKey: NUMMXFZHBMAYKM-PRJDIBJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-nitroethanol 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 乙酸酐 、 异氰酸苯酯 、 三乙胺 作用下， 以 苯 为溶剂， 反应 15.0h， 生成 5-ethoxy-3-<(4S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl>isoxazole
  参考文献：
  名称：

  A nitrile oxide based entry to 2,3-dihydropyran-4-ones. Synthesis of a protected version "compactin lactone" in racemic and optically active forms

  摘要：

  DOI：

  10.1021/jo00206a010
• 作为产物：
  描述：

  硝基甲烷 、 双丙酮-D-甘露糖醇 在 sodium periodate 、 四丁基氟化铵 作用下， 以 甲醇 、 水 、 四氢呋喃 为溶剂， 反应 13.0h， 以0.136 g的产率得到1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-nitroethanol
  参考文献：
  名称：

  CrudeD‐(+)‐Glyceraldehyde Obtained fromD‐Mannitol‐Diacetonide by Oxidative Cleavage with Sodium Periodate: Its Reactions with Nucleophilic Species

  摘要：

  The oxidative cleavage of D-(+)-mannitol-diacetonide with sodium periodate lead to a mixture of D-(+)-glyceraldehyde, its hydrate and oligomeric derivatives. In spite of the low concentration of free glyceraldehyde (estimated in similar to20%, by NMR), good yields were obtained in nucleophilic additions involving this mixture and a variety of nucleophiles (amines, phosphonates, phosphoranes, nitronates, organometallic compounds).

  DOI：

  10.1081/scc-120027706

文献信息

• Optically active nitroalkenes—synthesis, addition reactions and transformation into amino acids
  作者：Jan Hübner、Jürgen Liebscher、Michael Pätzel

  DOI：10.1016/s0040-4020(02)01406-0

  日期：2002.12

  Optically active nitroalkenes 4 were synthesized via Henry reaction. Conjugate addition of vinylmagnesium bromide to 4 gave nitroalkane syn-5 while cyclopropanation with sulfur ylides or dibromocarbene afforded nitrocyclopropanes 8, 10 and 11 in a diastereoselective manner. These products were used to synthesize optically active β-amino acids 7 and 16 as well as cyclopropane γ-amino acids 19 and 20

  通过亨利反应合成旋光性硝基烯烃4。共轭加成乙烯基溴化镁至4得到硝基烷烃顺- 5而环丙烷与硫叶立德或二溴卡宾得到nitrocyclopropanes 8，10和11在一个非对映选择性方式进行。这些产物用于通过还原硝基和二氧戊环取代基的氧化裂解来合成旋光性β-氨基酸7和16以及环丙烷γ-氨基酸19和20。
• [EN] PROCESS FOR PREPARING AMINOTETRAHYDROPYRANS<br/>[FR] PROCÉDÉ DE PRÉPARATION D'AMINOTÉTRAHYDROPYRANES
  申请人：F I S - FABBRICA ITALIANA SINTETICI S P A

  公开号：WO2017093209A1

  公开（公告）日：2017-06-08

  The present invention relates to a process for preparing 3-amino tetrahydropyrans and, more particularly, to an improved method for synthesizing a 2,3,5-substituted tetrahydropyran derivative, intermediate being used in the preparation of dipeptidyl peptidase-IV enzyme inhibitors (DPP-4 inhibitors).

  本发明涉及一种制备3-氨基四氢吡喃的方法，更具体地说，涉及一种改进的合成2,3,5-取代四氢吡喃衍生物的方法，该衍生物是用于制备二肽基肽酶IV酶抑制剂（DPP-4抑制剂）的中间体。
• 4M lithium perchlorate-nitromethane: An efficient solvent in Diels-Alder reactions using nitroalkenes as dienophiles
  作者：Mirari Ayerbe、Fernando P. Cossío

  DOI：10.1016/0040-4039(95)00678-6

  日期：1995.6

  Diels-Alder reactions in which nitroalkenes act as dienophiles are substantially accelerated in 4M lithium perchlorate-nitromethane solutions. This acceleration is higher than that observed when the known 5M lithium perchlorate-diethyl ether system is used.

  在4M高氯酸锂-硝基甲烷溶液中，硝基烯烃充当亲二烯体的Diels-Alder反应得到了显着加速。该加速度高于使用已知的5M高氯酸锂-乙醚系统观察到的加速度。
• Diastereoselective conjugate addition and cyclopropanation reactions with nitroalkenes derived from (R)-2,3-isopropylidene glyceraldehyde
  作者：Guido Galley、Jan Hübner、Sven Anklam、Peter G Jones、Michael Pätzel

  DOI：10.1016/0040-4039(96)01374-3

  日期：1996.8

  In the reactions of functionalized organometallics and of cyclopropanation reagents with chiral nitroalkenes 3 the conjugate addition proceeded with modest to high diastereoselectivity depending on the metal and the substituent R. X-ray analyses showed the nitrocyclopropanes 6, formed with high stereoselectivity, to be syn-derivatives.

  在官能化的有机金属和环丙烷化试剂与手性硝基烯烃3的反应中，根据金属和取代基R的不同，共轭加成反应的中等至高非对映选择性。X射线分析表明，具有高立体选择性的硝基环丙烷6是顺式-衍生品。
• Stereoselective aza-MIRC reactions on optically active (E)-nitro alkenes
  作者：Stefania Fioravanti、Fabio Marchetti、Lucio Pellacani、Luca Ranieri、Paolo A. Tardella

  DOI：10.1016/j.tetasy.2007.12.007

  日期：2008.2

  Optically active (E)-nitro alkenes carrying a 1,3-dioxolane or 1,3-oxazolidine residue undergo stereoselective aza-MIRC reactions, leading to the synthesis of the corresponding chiral nitro aziridines in high yields and with good diastereoselectivity. Interestingly, the stereochemical outcome of the aziridination reactions was strongly influenced by the chiral residue considered, giving stereoisomers

  带有1，3-二氧戊环或1，3-恶唑烷残基的旋光性（E）-硝基烯烃经历立体选择氮杂-MIRC反应，从而以高收率和良好的非对映选择性合成相应的手性硝基氮丙啶。有趣的是，所考虑的手性残基强烈影响叠氮化反应的立体化学结果，从而给出立体异构体，而与反应条件无关。