硝基乙醛缩二甲醇 | 69425-53-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 硝基乙醛缩二甲醇
• 中文别名: 1,1-二甲氧基-2-硝基乙烷
• 英文名称: 2,2-dimethoxy-1-nitroethane
• 英文别名: nitroacetaldehyde dimethyl acetal；2-nitroacetaldehyde dimethyl acetal；1,1-dimethoxy-2-nitro-ethane；1,1-Dimethoxy-2-nitroethane
• CAS: 69425-53-2
• 化学式: C₄H₉NO₄
• mdl: MFCD09751199
• 分子量: 135.12
• InChiKey: DSNXPQCFISEEMR-UHFFFAOYSA-N

物化性质

• 沸点：
  169 °C
• 密度：
  1.12
• 闪点：
  72 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• 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：

  顺式-4-甲基-2-戊烯 、 硝基乙醛缩二甲醇 在 异氰酸苯酯 、 三乙胺 作用下， 以 环戊烷 、 苯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Lewis acid promoted stereoselective carbon-carbon bond formation of 3-formyl-.DELTA.2-isoxazolines

  摘要：

  4,5-Disubstituted 3-formyl-DELTA2-isoxazolines undergo the aldol, allylation, and carbonyl ene reactions in the presence of appropriate Lewis acid to give the adducts with an effective 1,3-asymmetric induction. The stereoselectivity of the reaction mainly depends on the nature of the Lewis acid and the relative configuration of the ring. It is remarkable that both diastereomers can be readily prepared stereoselectively. For example, TiCl4 promotes the 1,3-syn-selective aldol reaction over 93/7 of selectivity, while the 1,3-anti adducts are prepared by the reaction catalyzed by BF3.OEt2. This difference in stereoselectivity is to be attributed to the preferable conformation of isoxazoline-Lewis acid complex intermediates, which depends on the nature of Lewis acid. Without the 4-substituent of isoxazolines the selectivity is not observed. The 5-substituent is too far from the formyl carbon to influence the face differentiation of the formyl group. Subsequent treatment of the adducts with LiAlH4 affords 2-amino 1,4-diol derivatives. The protective group of the hydroxyl group on the C(3) side chain is crucial for the stereoselectivity of the reduction. An almost complete diastereoselectivity of the relative configuration at four contiguous stereogenic centers is readily achieved by the reduction of the adducts protected by O-methoxymethyl (O-MOM). Consequently, the present strategy provides a facile method for the preparation of the compounds containing a sequence of several stereocenters.

  DOI：

  10.1021/jo00046a023
• 作为产物：
  描述：

  1-氯-2-硝基乙烯 、 sodium methylate 以 甲醇 为溶剂， 生成 硝基乙醛缩二甲醇
  参考文献：
  名称：

  Frankotte,F. et al., Bulletin des Societes Chimiques Belges, 1978, vol. 87, p. 693 - 707

  摘要：

  DOI：

文献信息

• 一种2-氯-5-硝基吡啶的制备方法
  申请人：新发药业有限公司

  公开号：CN111170933B

  公开（公告）日：2021-07-20

  本发明提供一种2‑氯‑5‑硝基吡啶的制备方法。以2‑硝基乙醛缩二醇为初始原料经由两种方法制备2‑羟基‑5‑硝基吡啶；然后2‑羟基‑5‑硝基吡啶和氯代试剂经氯代反应制备2‑氯‑5‑硝基吡啶。本发明方法原料价廉易得，成本低；不涉及重氮化水解反应，操作安全简便；不使用混酸，废水产生量少，绿色环保；同时不涉及硝化反应，反应选择性高，副反应少，后处理简单，产品收率和纯度高，适于工业化生产。
• II. 1,3-Dipolar cycloadditions to unsaturated boronic esters. Synthesis of borylated 2-isoxazolines. Conversion of some cycloadducts to 5-hydroxy-2-isoxazolines, 5-hydroxymethyl-2-isoxazolines and isoxazoles
  作者：M. Jazouli、S. Baba、B. Carboni、R. Carrié、M. Soufiaoui

  DOI：10.1016/0022-328x(95)05531-s

  日期：1995.8

  2-isoxazolines was prepared by 1,3-cycloaddition reactions of nitrile oxides to vinyl- and allylboronic esters. The influence of substituents on the reactivity, the regio- and stereoselectivity was examined and some examples of cycloadduct oxidation were described.

  通过腈氧化物与乙烯基和烯丙基硼酸酯的1，3-环加成反应制备了各种硼化的2-异恶唑啉。考察了取代基对反应性，区域选择性和立体选择性的影响，并描述了环加合物氧化的一些实例。
• Preparation of 5-unsubstituted 4-formylpyrrole-2-carboxylates and conversion to cycloalkano-oligopyrroles †
  作者：Yumiko Fumoto、Hidemitsu Uno、Satoshi Ito、Yuka Tsugumi、Maki Sasaki、Yukiko Kitawaki、Noboru Ono

  DOI：10.1039/b003360j

  日期：——

  Ethyl 4-formylpyrrole-2-carboxylates were prepared from nitroacetaldehyde dimethyl acetal in 9–50% yields using the Barton–Zard reaction. These formylpyrroles were successfully transformed to cycloalkano-oligopyrroles. The conformation of cyclononatripyrroles in CDCl3 was found to be a crown form based on the NMR analysis, while cyclododecatetrapyrroles were in two interconverting boat and chair conformations.

  利用 Barton-Zard 反应从硝基乙醛二甲基缩醛制备了 4-甲酰基吡咯-2-羧酸乙酯，收率为 9-50%。这些甲酰基吡咯被成功转化为环烷-寡聚吡咯。根据核磁共振分析，发现环酮三吡咯在 CDCl3 中的构象为冠型，而环十二烷四吡咯则有两种相互转化的舟型和椅型构象。
• Facile Preparation of α-Nitroaldehyde Acetals from (<i>E/Z</i>)-2-Nitro-1-phenylthio-1-alkenes
  作者：Akio Kamimura、Tomoaki Nagashima

  DOI：10.1055/s-1990-26984

  日期：——

  The reaction of (E/Z)-2-nitro-1-phenylthio-1-alkenes with alkoxides provided a new method for the preparation of 1,1-dibenzyloxy- and 1,1-dialkoxy-2-nitroalkanes.

  (E/Z)-2-硝基-1-苯硫基-1-烯烃与醇盐的反应为制备1,1-二苄氧基-和1,1-二烷氧基-2-硝基烷烃提供了新的方法。
• N-[3-(5-AMINO-3,3A,7,7A-TETRAHYDRO-1H-2,4-DIOXA-6-AZA-INDEN-7-YL)-PHENYL]-AMIDES AS BACE1 AND/OR BACE2 INHIBITORS
  申请人：Hilpert Hans

  公开号：US20120202803A1

  公开（公告）日：2012-08-09

  The present invention relates to N-[3-(5-Amino-3,3a,7,7a-tetrahydro-1H-2,4-dioxa-6-aza-inden-7-yl)-phenyl]-amides of formula I having BACE1 and/or BACE2 inhibitory activity, their manufacture, pharmaceutical compositions containing them and their use as therapeutically active substances. The active compounds of the present invention are useful in the therapeutic and/or prophylactic treatment of e.g. Alzheimer's disease and type 2 diabetes.

  本发明涉及具有BACE1和/或BACE2抑制活性的式I的N-[3-(5-氨基-3,3a,7,7a-四氢-1H-2,4-二氧杂-6-氮杂-茚-7-基)-苯基]-酰胺，其制造，包含它们的制药组合物以及它们作为治疗活性物质的用途。本发明的活性化合物在治疗和/或预防治疗阿尔茨海默病和2型糖尿病等方面是有用的。