5,5-Dimethoxy-1-hexen | 88441-62-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5-Dimethoxy-1-hexen
• 英文别名: 5-hexen-2-one dimethyl ketal；5,5-Dimethoxyhexene；5,5-Dimethoxyhex-1-ene
• CAS: 88441-62-7
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: BPFZNZMTZDOWIF-UHFFFAOYSA-N

物化性质

• 沸点：
  153.1±33.0 °C(Predicted)
• 密度：
  0.856±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5-Dimethoxy-1-hexen 在 三氟化硼乙醚 、 potassium hydride 、 溶剂黄146 、 甲苯 、 三氟乙酸 、 copper(l) chloride 、 palladium dichloride 、 β-丙氨酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.17h， 生成 1-(Z)-ethylidene-7a-methyl-2,3,7,7a-tetrahydro-5(6H)-indanone
  参考文献：
  名称：

  Ring expansion and cleavage of succinoin derivatives. Geminal acylation, reductive succinoylation, and stereoselective spiro annelation methods

  摘要：

  DOI：

  10.1021/ja00318a035
• 作为产物：
  描述：

  5-已烯-2-酮 、 原甲酸三甲酯 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 5,5-Dimethoxy-1-hexen
  参考文献：
  名称：

  Conjugation Chemistry through Acetals toward a Dextran-Based Delivery System for Controlled Release of siRNA

  摘要：

  New conjugation chemistry for polysaccharides, exemplified by dextran, was developed to enable the attachment of therapeutic or other functional moieties to the polysaccharide through cleavable acetal linkages. The acid-lability of the acetal groups allows the release of therapeutics under acidic conditions, such as that of the endocytic compartments of cells, regenerating the original free polysaccharide in the end. The physical and chemical behavior of these acetal groups can be adjusted by modifying their stereoelectronic and steric properties, thereby providing materials with tunable degradation and release rates. We have applied this conjugation chemistry in the development of water-soluble siRNA carriers, namely acetal-linked amino-dextrans, with various amine structures attached through either slow- or fast-degrading acetal linker. The with the best combination of amine moieties and structural composition of acetals showed high in vitro transfection efficiency and low cytotoxicity in the delivery of siRNA.

  DOI：

  10.1021/ja305552u

文献信息

• Ketal claisen rearrangements of functionalized ketals
  作者：G.William Daub、Sharon R. Lunt

  DOI：10.1016/s0040-4039(00)85907-9

  日期：1983.1

  Functionalized ketals participate successfully in the acid-catalyzed ketal Claisen rearrangement to afford mixtures of the isomeric γ,δ-unsaturated ketones, with the more highly substituted isomer predominating by a factor of 2–4:1.

  功能化的缩酮成功地参与了酸催化的缩酮Claisen重排，从而提供了异构体γ，δ-不饱和酮的混合物，取代度更高的异构体的比例为2-4：1。
• Kirmse, Wolfgang; Sandkuehler, Peter, Liebigs Annalen der Chemie, 1981, # 8, p. 1394 - 1406
  作者：Kirmse, Wolfgang、Sandkuehler, Peter

  DOI：——

  日期：——
• Triisobutylaluminun (TIBA) as a reagent to convert 2,2-dimethoxyalkanes to 2-methoxy-1-alkenes
  作者：Gustavo Cabrera、Rita Fiaschi、Elio Napolitano

  DOI：10.1016/s0040-4039(01)01141-8

  日期：2001.8

  Methanol ketals undergo methanol elimination by reaction with triisobutylaluminum to yield the corresponding less substituted 2-methoxyolefins; the experimental conditions are compatible with the Presence of other functional groups. (C) 2001 Elsevier Science Ltd. All rights reserved.
• DAUB, G. W.;LUNT, S. R., TETRAHEDRON LETT., 1983, 24, N 41, 4397-4400
  作者：DAUB, G. W.、LUNT, S. R.

  DOI：——

  日期：——
• SHIMADA, J. -ICHI;HASHIMOTO, KOICHI;KIM, BYEANG, HYEAN;NAKAMURA, EIICHI;K+, J. AMER. CHEM. SOC., 1984, 106, N 6, 1759-1773
  作者：SHIMADA, J. -ICHI、HASHIMOTO, KOICHI、KIM, BYEANG, HYEAN、NAKAMURA, EIICHI、K+

  DOI：——

  日期：——