(3aR,5S,6S,6aR)-6-[(E)-but-2-enoxy]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde | 402559-33-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5S,6S,6aR)-6-[(E)-but-2-enoxy]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde
• CAS: 402559-33-5
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: SZWXICDTLNEADG-WDESZPRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,5S,6S,6aR)-6-[(E)-but-2-enoxy]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 以80%的产率得到(2'E)-3-O-(2'-butenyl)-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose oxime
  参考文献：
  名称：

  Synthesis, high-resolution NMR spectroscopic analysis, and single-crystal X-ray diffraction of isoxazoline tetracycles

  摘要：

  Three isoxazoline tetracycles were obtained enantiomerically pure by intramolecular 1,3-dipolar cycloaddition. The characterization of the new compounds was performed by high-resolution H-1 and C-13 NMR spectroscopy. The relative configuration of the new chiral centers was determined by NOESY experiments and confirmed by single-crystal X-ray structural analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00258-6
• 作为产物：
  描述：

  (2'E)-3-O-(2'-butenyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 sodium periodate 、 溶剂黄146 作用下， 以 氯仿 、 水 为溶剂， 反应 16.0h， 生成 (3aR,5S,6S,6aR)-6-[(E)-but-2-enoxy]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde
  参考文献：
  名称：

  3- O-烯丙基碳水酮硝酮环加成（3-OACNC）合成手性氧杂环丁烷和吡喃

  摘要：

  3- ø从3- -Allylcarbohydrate硝酮环加成（3- OACNC）布置吡喃和氧杂环庚烷衍生物ø -烯丙基己糖ñ -苄基硝酮和3- ö烯丙基呋喃-5-醛ñ -苄基/甲基硝酮。发现3-OACNC的区域选择性取决于以下因素（a）硝酮的结构性质（b）碳水化合物主链在3-C处的取代和立体化学（c）在O末端的取代-烯丙基部分。从特定组的己糖硝酮和相应的呋喃糖苷硝酮获得的氧杂环丁烷或吡喃通过降解转化为对映体环状醚。在3- O-烯丙基碳水合物衍生的肟的分子内肟环烯烃加成反应（IOOC ）中形成环氧丙烷和吡喃的混合物。

  DOI：

  10.1016/s0040-4020(03)00634-3

文献信息

• ‘Off-template site’ intramolecular nitrone cycloaddition (INC) reactions on sugar-derived allylic ethers—a study on the substituent effect and synthesis of furano-pyrans
  作者：G.V.M Sharma、K Ravinder Reddy、A Ravi Sankar、A.C Kunwar

  DOI：10.1016/s0040-4039(01)01889-5

  日期：2001.12

  Sugar-derived allylic ethers having one or two substituents on the terminal olefinic carbon centre were subjected to intramolecular nitrone cycloaddition (INC) reactions resulting in bicyclo[4.3.0] systems. The exclusiveness of product formation may be attributed to the effect of substituents.

  将在末端烯烃碳中心具有一个或两个取代基的糖衍生的烯丙基醚进行分子内硝酮环加成（INC）反应，生成双环[4.3.0]系统。产物形成的排他性可以归因于取代基的作用。
• Stereoselective Synthesis of Chiral Oxepanes and Pyrans through Intramolecular Nitrone Cycloaddition in Organized Aqueous Media
  作者：Amrita Chatterjee、Pranab K. Bhattacharya

  DOI：10.1021/jo051414j

  日期：2006.1.1

  A highly stereoselective surfactant-catalyzed intramolecular nitrone (formed by dehydration in water) cycloaddition in aqueous media leading to exclusive formation of a single isomer is reported. Either oxepane or pyran is formed from 3-O-allyl furanoside derivatives, which constitute the framework of a large number of biologically active compounds. Therefore, the environmentally friendly, efficient

  据报道，在水性介质中高度立体选择性的表面活性剂催化的分子内硝酮（通过在水中脱水形成）环加成导致独家形成单个异构体。环氧丙烷或吡喃由3- O-烯丙基呋喃糖苷衍生物形成，其构成大量生物活性化合物的框架。因此，这些手性中间体的环保，有效和高度立体选择性的合成仍然是有意义的追求。
• Increased formation of oxepanes in non-aqueous medium in the cycloaddition of 3-O-allyl-1,2-isopropylidenefuranose N-Ph nitrones
  作者：Seema Datta、Madhumita Nath、Sandip Chowdhury、Anup Bhattacharjya

  DOI：10.1016/j.tetlet.2008.03.014

  日期：2008.4

  Cycloaddition of 3-O-allyl-1,2-isopropylidene N-Ph nitrones afforded appreciably increased yields of oxepanes compared to the corresponding N-Me or N-Bn nitrones. Higher yields permitted some useful further transformations of the oxepanes. (c) 2008 Elsevier Ltd. All rights reserved.