3,3-二乙氧基-1-丙炔基溴化镁 | 69309-71-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: 3,3-二乙氧基-1-丙炔基溴化镁
• 英文名称: 3,3-diethoxy-1-propynylmagnesium bromide
• 英文别名: 3,3-diethoxyprop-1-ynylmagnesium bromide；(3,3-diethoxy-prop-1-ynyl)-magnesium bromide；propiolaldehyde diethylacetal; compound with magnesium bromide；Propiolaldehyd-diaethylacetal; Verbindung mit Magnesiumbromid；3,3-Diaethoxy-prop-1-inylmagnesiumbromid
• CAS: 69309-71-3
• 化学式: C₇H₁₁BrMgO₂
• 分子量: 231.372
• InChiKey: WAMSKIANHONGMB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,3-二乙氧基-1-丙炔基溴化镁 在 sodium carbonate 、 硫酸肼 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 40.0h， 生成 (2'S)-3(5)-(2'-N-tert-butoxycarbonylpyrrolidinyl)-5(3)-(1,1-diethoxymethyl)pyrazole
  参考文献：
  名称：

  Synthesis of chiral pyrazoles and isoxazoles as constrained amino acids

  摘要：

  A stereospecific syntheses of optically active pyrazoles and isoxazoles from L-proline is described. The procedure presented is based on readily available materials and can be used for preparing new conformationally restricted pyrazole-containing amino acids, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00305-x

文献信息

• Highly Regioselective α-Addition of Alkynyl and Alkenyl Grignard Reagents to 1-Alkoxycarbonylpyridinium Salts and Its Application to Synthesis of 1-Azabicycloalkanes and (±)-Solenopsin A
  作者：Ryohei Yamaguchi、Yutaka Nakazono、Toshitsugu Matsuki、Ei-ichiro Hata、Mituyosi Kawanisi

  DOI：10.1246/bcsj.60.215

  日期：1987.1

  Nucleophilic addition of a variety of alkynyl and alkenyl Grignard reagents to 1-methoxycarbonylpyridinium chloride takes place at the α-position in a highly regioselective manner to give 2-substituted 1-methoxycarbonyl-1,2-dihydropyridines exclusively, while, with alkyl Grignard reagents, a lack of the regioselectivity is observed. These results may be explained by the HSAB principle. The high α-regioselectivity

  各种炔基和烯基格氏试剂与 1-甲氧基羰基氯化吡啶的亲核加成以高度区域选择性的方式在 α-位发生，以专门产生 2-取代的 1-甲氧基羰基-1,2-二氢吡啶，而使用烷基格氏试剂，观察到缺乏区域选择性。这些结果可以用 HSAB 原理来解释。在 2-取代吡啶的情况下也保持了高 α-区域选择性，仅得到 2,6-二取代的 1,2-二氢吡啶，其可以立体选择性地转化为顺式和反式 2,6-二烷基化哌啶。1-甲氧羰基吡啶鎓盐的这些高度区域选择性的α-炔基化被用于合成1-氮杂双环烷烃和(±)-solenopsin A。
• Synthesis of 4-hydroxy[4-3H]-2(E)-nonen-1-al-diethylacetal
  作者：Fabienne Bravais、Dinesh Rao、Jacques Alary、Renée C. Rao、Laurent Debrauwer、Georges Bories

  DOI：10.1002/jlcr.2580360511

  日期：1995.5

  4-Hydroxy-2(E)-nonen-1-al-diethylacetal 3 (HNE-DEA) was prepared by condensation of the Grignard compound derived from propiolaldehyde diethylacetal and n-hexanal followed by reduction of the resulting 4-hydroxy-2-nonyn-1-al-diethylacetal 2 with LiAlH4 according to the literature procedure with minor modifications. Swern oxidation [DMSO + (COCl2)] of 3 gave 30% yield of 4-oxo-2(E)-nonen-1-al-diethylacetal 5. [3H]NaBH4 and [2H]NaBH4 reduction of 5 gave rise respectively to [4-3H]HNE-DEA (specific activity 222 GBq/mmol) and [4-2H]HNE-DEA.

  4- 羟基-2(E)-壬烯-1-醛二乙缩醛 3 (HNE-DEA)的制备方法是：先用丙炔醛二乙缩醛和正己醛缩合得到的格氏化合物，然后根据文献中的方法稍加改动，用 LiAlH4 还原得到的 4- 羟基-2-壬烯-1-醛二乙缩醛 2。对 3 进行[DMSO + (COCl2)]Swern 氧化，得到 30% 产率的 4-氧代-2(E)-壬烯-1-al-二乙缩醛 5。5 的 [3H]NaBH4 和 [2H]NaBH4 还原分别得到 [4-3H]HNE-DEA（比活度 222 GBq/mmol）和 [4-2H]HNE-DEA。
• A new synthesis of formycin via nitropyrazole derivatives
  作者：J. Grant Buchanan、Alan R. Edgar、Roderick J. Hutchison、Alan Stobie、Richard H. Wightman

  DOI：10.1039/c39800000237

  日期：——

  3-(2,3,5-Tri-O-benzyl-β-D-ribofuranosyl)pyrazole (4) has been converted into formycin (15) by a sequence involving, as the key step, cine substitution, by cyanide ion, of the 1-nitro group in the 1,4-dinitropyrazole (10).

  3-（2,3,5-Tri- O-苄基-β - D-呋喃呋喃糖基）吡唑（4）已通过一个序列被转化为甲霉素（15），该序列的关键步骤是通过氰化物离子将电影取代， 1,4-二硝基吡唑中的1-硝基基团（10）。
• Inhibitors of nucleoside metabolism
  申请人：——

  公开号：US20020061898A1

  公开（公告）日：2002-05-23

  The present invention provides novel nucleoside-analogue compounds that are effective inhibitors of purine nucleoside phosphorylase (PNP), purine phosphoribosyltransferases (PPRT), and/or nucleoside hydrolases. Also provided are tautomers, esters, prodrugs, and pharmaceutically-acceptable salts of the compounds disclosed herein. The present invention further provides the use of these compounds as pharmaceuticals. The present invention also discloses pharmaceutical compositions containing these compounds. Finally, the present invention provides processes for preparing these compounds.

  本发明提供了新型核苷类似物化合物，它们是嘌呤核苷酸磷酸酶（PNP）、嘌呤磷酸核糖转移酶（PPRT）和/或核苷水解酶的有效抑制剂。此外，还提供了这些化合物的互变异构体、酯、前药和药学上可接受的盐。本发明进一步提供了这些化合物作为药物的用途。本发明还揭示了含有这些化合物的制药组合物。最后，本发明提供了制备这些化合物的过程。
• Synthese einiger 4-Hydroxy-2-alkenale
  作者：H. Esterbauer

  DOI：10.1007/bf01167265

  日期：1971.5