(S)-2,2-dimethyl-4-(2-nitroethyl)-1,3-dioxolane | 94370-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2,2-dimethyl-4-(2-nitroethyl)-1,3-dioxolane
• 英文别名: (2S)-(Isopropylidenedioxy)-4-nitrobutane；(4S)-2,2-dimethyl-4-(2-nitroethyl)-1,3-dioxolane
• CAS: 94370-97-5
• 化学式: C₇H₁₃NO₄
• 分子量: 175.185
• InChiKey: XJZDGGSLGJBVJX-LURJTMIESA-N

物化性质

• 沸点：
  88-90 °C(Press: 1 Torr)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 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：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2,2-dimethyl-4-(2-nitroethyl)-1,3-dioxolane 在 镍 氢气 、 异氰酸苯酯 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 24.0h， 生成 (S)-ethyl 4-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-oxobutanoate
  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：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 4-二甲氨基吡啶 、 potassium fluoride 、 sodium tetrahydroborate 、 乙酸酐 作用下， 以 异丙醇 为溶剂， 反应 3.0h， 生成 (S)-2,2-dimethyl-4-(2-nitroethyl)-1,3-dioxolane
  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

文献信息

• [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。
• Process for preparing aminotetrahydropyrans
  申请人：F.I.S.—Fabbrica Italiana Sintetici S.p.A.

  公开号：US10377732B2

  公开（公告）日：2019-08-13

  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-氨基四氢吡喃的工艺，更具体地说，涉及一种合成2,3,5-取代的四氢吡喃衍生物的改进方法，该衍生物中间体可用于制备二肽基肽酶-IV酶抑制剂（DPP-4抑制剂）。
• Synthesis of 3-(trans-2'-Nitrocyclopropyl)alanine, a Constituent of the Natural Peptide-Lactone Hormaomycin
  作者：Juergen Zindel、Armin de Meijere

  DOI：10.1021/jo00115a009

  日期：1995.5

  The peptide-lactone hormaomycin 1a produced by Streptomyces griseoflavus contains two molecules of 3-(trans-2'-nitrocyclopropyl)alanine [Ala(3-Ncp)] (6). In order to determine the unknown absolute configurations of these unusual natural amino acid molecules, which supposedly are essential for the biological activity of 1a, enantiopure alcohols (trans-2-nitrocyclopropyl)methanol [(1S,2S)-13 and (1R,2R)-13] have been prepared in six steps from (R)- and (S)-2,3-O-isopropylideneglyceral-dehyde (17). The alcohols 13 were transformed to the bromides 23, and these in turn were coupled with suitable glycine equivalents like 2-[(diphenylmethylene)amino]acetates (24) to yield (2R/S,1'S,2'S)- and (2R/S,1'R,2'R)-3-(trans-2'-nitrocyclopropyl)alanines (6), after deprotection. The natural compound la contains one molecule each with (2R,1'R,2'R)- and (2S,1'R,2'R)-configuration, as established by comparison of the hydrolysate from natural la with the synthesized samples of (2R/S,1'R,2'R)-6 and (2R/S,1'S,2'S)-6.
• Synthesis of 3-(trans-2′-nitrocyclopropyl)alanine: An unusual natural amino acid
  作者：Jürgen Zindel、Axel Zeeck、Wilfried A. König、Armin de Meijere

  DOI：10.1016/s0040-4039(00)91962-2

  日期：1993.3

  Racemic (trans-2'-nitrocyclopropyl)methanol rac-7 is prepared in three steps from t-butyl acrylate, while enantiopure (1'S,2'S)-7 and (1'R,2'R)-7 is obtained in six steps from (R)- and (S)-2,3-O-isopropylideneglyceraldehyde, respectively. The alcohol 7 can be transformed to the bromide 8 and this in turn coupled with the glycine equivalent 2-(diphenylmethylenamino)acetate 9 to yield 3-(trans-2'-nitrocyclopropyl)alanine (Ala(3-Ncp)) 11, after deprotection. The natural material, part of the peptide-lactone hormaomycin, has (1'R,2'R)-configuration, as determined by comparison with the synthesized authentic compounds.
• KOZIKOWSKI, A. P.;LI, CHUN-SING, J. ORG. CHEM., 1985, 50, N 6, 778-785
  作者：KOZIKOWSKI, A. P.、LI, CHUN-SING

  DOI：——

  日期：——