3-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]propanal | 107691-81-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]propanal
• CAS: 107691-81-6
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: IYBXVFCOXMUESD-VIFPVBQESA-N

物化性质

• 沸点：
  219.8±15.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]propanal 在 potassium osmate(VI) 、 dipotassium peroxodisulfate 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 mercury(II) diacetate 、 4-甲基苯磺酸吡啶 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 potassium carbonate 、 戴斯-马丁氧化剂 、 甲基磺酰氯 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 35.83h， 生成 (7S)-7-(4-methoxybenzyloxy)-9-(tert-butyldiphenylsilyloxy)-7-methyl-1-((S)-2-methyloxiran-2-yl)nonane-3,4-diol
  参考文献：
  名称：

  Pectenotoxin-2 Synthetic Studies. 3. Assessment of the Capacity for Stereocontrolled Cyclization To Form the Entire C1−C26 Subunit Based upon the Double Bond Geometry Across C15-C16

  摘要：

  Second-generation synthetic routes to enantiopure sulfone 21 and aldehyde 24 are described. The union of these two intermediates by means of a Julia-Kocienski coupling gave rise to a series of E-configured building blocks that did not prove amenable to transannular cyclization. Alternatively, when the C15-C16 double bond was introduced with Z-geometry by Wittig olefination, spontaneous closure to generate a tetrahydrofuran culminated an ensuing direct dihydroxylation step. The structural assignment to 35, undergirded by detailed H-1 and C-13 NMR studies, is consistent with proper transannular bonding so as to deliver the entire C1-C26 fragment of PTX2.

  DOI：

  10.1021/jo062513f
• 作为产物：
  描述：

  2-methyl-5-oxotetrahydrofuran-2-carboxylic acid 在 lithium aluminium tetrahydride 、 对甲苯磺酸 、 二甲基亚砜 、 三氟乙酸酐 、 辛可宁 作用下， 以 二氯甲烷 、 三乙胺 为溶剂， 反应 30.0h， 生成 3-[(4S)-2,2,4-trimethyl-1,3-dioxolan-4-yl]propanal
  参考文献：
  名称：

  Synthesis of two key intermediates required for the construction of the bis-spiroacetal moiety of epi-17-deoxy-(0–8)-salinomycin

  摘要：

  DOI：

  10.1016/s0040-4039(00)84784-x

文献信息

• Pectenotoxin-2 Synthetic Studies. 2. Construction and Conjoining of ABC and DE Eastern Hemisphere Subtargets
  作者：Dmitriy Bondar、Jian Liu、Thomas Müller、Leo A. Paquette

  DOI：10.1021/ol0504291

  日期：2005.4.1

  [reaction: see text] Practical asymmetric synthesis of aldehyde 2 and tetrazolyl sulfone 3 has allowed for their coupling via Julia olefination to generate 32 as a single product. This substance possesses the entire carbon backbone of the A-E substructure of pectenotoxin-2.

  [反应：见正文]醛2和四唑基砜3的实际不对称合成已允许它们通过朱莉亚烯化反应进行偶联，从而生成32个单一产物。该物质具有果胶毒素2的AE亚结构的整个碳主链。
• Synthesis of two key intermediates required for the construction of the bis-spiroacetal moiety of epi-17-deoxy-(0–8)-salinomycin
  作者：Raymond Baker、Margaret A. Brimble

  DOI：10.1016/s0040-4039(00)84784-x

  日期：1986.1
• Pectenotoxin-2 Synthetic Studies. 3. Assessment of the Capacity for Stereocontrolled Cyclization To Form the Entire C1−C26 Subunit Based upon the Double Bond Geometry Across C15-C16
  作者：Patrick D. O'Connor、Christopher K. Knight、Dirk Friedrich、Xiaowen Peng、Leo A. Paquette

  DOI：10.1021/jo062513f

  日期：2007.3.1

  Second-generation synthetic routes to enantiopure sulfone 21 and aldehyde 24 are described. The union of these two intermediates by means of a Julia-Kocienski coupling gave rise to a series of E-configured building blocks that did not prove amenable to transannular cyclization. Alternatively, when the C15-C16 double bond was introduced with Z-geometry by Wittig olefination, spontaneous closure to generate a tetrahydrofuran culminated an ensuing direct dihydroxylation step. The structural assignment to 35, undergirded by detailed H-1 and C-13 NMR studies, is consistent with proper transannular bonding so as to deliver the entire C1-C26 fragment of PTX2.