1,3-二氯丙烷-2-酮O-苄基-肟 | 188125-86-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,3-二氯丙烷-2-酮O-苄基-肟
• 英文名称: 1,3-dichloro-2-propanone O-benzyloxime
• 英文别名: 1,3-dichloropropan-2-one O-benzyloxime；1,3-Dichloro-propan-2-one O-benzyl-oxime；1,3-dichloro-N-phenylmethoxypropan-2-imine
• CAS: 188125-86-2
• 化学式: C₁₀H₁₁Cl₂NO
• 分子量: 232.109
• InChiKey: FBIHQCYFKGDZEM-UHFFFAOYSA-N

物化性质

• 沸点：
  307.5±52.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-二氯丙烷-2-酮O-苄基-肟 在 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 一水合肼 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 N,N'-{2-[(benzyloxy)imino]propane-1,3-diyl}-bis[(2R)-2,3-dihydroxypropanamide]
  参考文献：
  名称：

  Synthetic studies towards 4,10-diaza-1,7-dioxaspiro[5.5]undecanes: access to 3-aza-6,8-dioxabicyclo[3.2.1]octan-2-one and 2H-1,4-oxazin-3(4H)-one frameworks

  摘要：

  Synthetic approaches towards 4,10-diaza-1,7-dioxaspiro[5.5] undecanes starting from 1,3-dichloroacetone and solketal derivatives are explored. The method relies on the preparation of a key bis-substituted dihydroxy-protected oxime, which would undergo a final acidic deprotection-spiroacetalization process. Although the desired diazaspiroketal framework could not be obtained, our conditions led to the unexpected 3-aza-6,8-dioxabicyclo[3.2.1] octan-2-one 18 or to the oxazinone 32 in good yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.109
• 作为产物：
  描述：

  苄氧基胺盐酸盐 、 1,3-二氯丙酮 以 乙醇 为溶剂， 反应 24.0h， 以2.32 g的产率得到1,3-二氯丙烷-2-酮O-苄基-肟
  参考文献：
  名称：

  Synthetic studies towards 4,10-diaza-1,7-dioxaspiro[5.5]undecanes: access to 3-aza-6,8-dioxabicyclo[3.2.1]octan-2-one and 2H-1,4-oxazin-3(4H)-one frameworks

  摘要：

  Synthetic approaches towards 4,10-diaza-1,7-dioxaspiro[5.5] undecanes starting from 1,3-dichloroacetone and solketal derivatives are explored. The method relies on the preparation of a key bis-substituted dihydroxy-protected oxime, which would undergo a final acidic deprotection-spiroacetalization process. Although the desired diazaspiroketal framework could not be obtained, our conditions led to the unexpected 3-aza-6,8-dioxabicyclo[3.2.1] octan-2-one 18 or to the oxazinone 32 in good yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.109

文献信息

• Synthesis of biotinylated bis(d-glucose) derivatives for glucose transporter photoaffinity labelling
  作者：Makoto Hashimoto、Yasumaru Hatanaka、Jing Yang、Jaswant Dhesi、Geoffrey D. Holman

  DOI：10.1016/s0008-6215(01)00025-8

  日期：2001.3

  New diazirine based bis-glucose derivatives for tagging glucose transporters have been synthesised. These included two biotinylated compounds linked either by an aminocaproate or by a cleavable dithiol link. These compounds have been derivatised via a key skeleton compound that can be easily used for introduction of additional tags. Studies on the erythrocyte glucose transporter (GLUT1) and the insulin-stimulated

  已经合成了用于标记葡萄糖转运蛋白的新的基于二嗪啉的双葡萄糖衍生物。这些包括通过氨基己酸酯或通过可裂解的二硫醇键连接的两种生物素化化合物。这些化合物已通过关键骨架化合物衍生化，该骨架化合物可轻松用于引入其他标签。对红细胞葡萄糖转运蛋白（GLUT1）和胰岛素刺激的脂肪细胞转运蛋白（GLUT4）的研究表明，生物素化的光反应性双葡萄糖化合物是有效的标记试剂。
• A flexible route to new spirodioxanes, oxathianes, and morpholines
  作者：Marlène Goubert、Isabelle Canet、Marie-Eve Sinibaldi

  DOI：10.1016/j.tet.2009.03.044

  日期：2009.5

  This work describes a modular efficient route to 10-aza-4-thia-, 10-aza-4-oxa-, and 10-oxa-4-thia-1,7-dioxaspiro[5.5]undecanes. The synthetic pathway relies upon the iterative nucleophilic substitution of 1,3-dichloropropan-2-one O-benzyloxime by solketal derivatives. The oxime key-intermediates, submitted to an acidic deprotection-spiroacetalization process, afforded these original spiroketal compounds in three steps, few purifications, and very good yields. (C) 2009 Elsevier Ltd. All rights reserved.
• A practical synthesis of ATB-[2-3H] BMPA, a photolabelling reagent for exofacial glucose transporters
  作者：Philip M. Sher、David R. Kronenthal

  DOI：10.1002/(sici)1099-1344(199701)39:1<21::aid-jlcr937>3.0.co;2-2

  日期：1997.1

  Major improvements in the efficiency of ATB-[2-H-3]BMPA synthesis were achieved by using 1,3-dichloro-2-propanone O-benzyloxime (6) as the linking reagent.