2-Ethoxy-2-(3-iodo-propyl)-[1,3]dioxolane | 198895-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Ethoxy-2-(3-iodo-propyl)-[1,3]dioxolane
• 英文别名: 2-Ethoxy-2-(3-iodopropyl)-1,3-dioxolane
• CAS: 198895-90-8
• 化学式: C₈H₁₅IO₃
• 分子量: 286.11
• InChiKey: KUAQFOJECHDKOR-UHFFFAOYSA-N

物化性质

• 沸点：
  283.2±35.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Ethoxy-2-(3-iodo-propyl)-[1,3]dioxolane 在 samarium diiodide 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 C₁₁H₁₈O₃
  参考文献：
  名称：

  Efficient access to functionalised medium-ring systems by radical fragmentation/radical addition to α-iodoketones

  摘要：

  Functionalised medium-ring systems of various sizes can be efficiently prepared by a novel approach that embodies a radical-induced fragmentation of bicyclic P-hydroxy ketones, followed by a second radical-coupling reaction. The unexpected reactivity of ot-keto radicals is also discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.200
• 作为产物：
  描述：

  2-(3-chloropropyl)-2-ethoxy-1,3-dioxolane 在 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 2-Ethoxy-2-(3-iodo-propyl)-[1,3]dioxolane
  参考文献：
  名称：

  用于快速有效构建双环 [4.n.0] 烷醇和烯酮的新型退火方法

  摘要：

  一系列稠合双环醇和烯酮的有效组装可以使用新颖的、基于原酸酯的退火方法轻松进行。

  DOI：

  10.1055/s-1999-2768

文献信息

• Stereoselective synthesis of bicyclic lactones by annelation with functionalised orthoesters
  作者：Nuno Maulide、István E. Markó

  DOI：10.1039/b600677a

  日期：——

  An efficient two-step annelation of functionalised orthoesters with trimethylsilyloxyfuran derivatives, which delivers suitably decorated bicyclo[3.n.0]lactones in high overall yields and with complete diastereocontrol of up to three contiguous stereocenters, is reported.

  报告介绍了一种用三甲基硅氧基呋喃衍生物对官能化的原酯进行两步醛化的高效方法，该方法能以较高的总收率提供经适当修饰的双环[3.n.0]内酯，并能完全非对映地控制多达三个连续的立体中心。
• 2-(Trimethylsilyloxy)furan as a Dianion Equivalent:  A Two-Step Synthesis of Functionalized Spirocyclic Butenolides
  作者：Nuno Maulide、István E. Markó

  DOI：10.1021/ol061284g

  日期：2006.8.1

  [reaction: see text] The use of 2-(trimethylsilyloxy)furan derivatives as dianion equivalents leads to a general and connective spiroannulation protocol for the efficient preparation of spirocyclic butenolides.

  [反应：见正文]使用2-（三甲基甲硅烷氧基）呋喃衍生物作为二价阴离子等效物可产生通用的和连接的螺环化方案，以有效地制备螺环式丁烯内酯。
• Straightforward and effective synthesis of γ-aminobutyric acid transporter subtype 2-selective acyl-substituted azaspiro[4.5]decanes
  作者：Xiaofeng Ma、Hodney Lubin、Enikő Ioja、Orsolya Kékesi、Ágnes Simon、Ágota Apáti、Tamás I. Orbán、László Héja、Julianna Kardos、István E. Markó

  DOI：10.1016/j.bmcl.2015.11.100

  日期：2016.1

  Supply of major metabolites such as gamma-aminobutyric acid (GABA), beta-alanine and taurine is an essential instrument that shapes signalling, proper cell functioning and survival in the brain and peripheral organs. This background motivates the synthesis of novel classes of compounds regulating their selective transport through various fluid-organ barriers via the low-affinity gamma-aminobutyric acid (GABA) transporter subtype 2 (GAT2). Natural and synthetic spirocyclic compounds or therapeutics with a range of structures and biological activity are increasingly recognised in this regard. Based on pre-validated GABA transport activity, straightforward and efficient synthesis method was developed to provide an azaspiro[4.5]decane scaffold, holding a variety of charge, substituent and 3D constrain of spirocyclic amine. Investigation of the azaspiro[4.5]decane scaffold in cell lines expressing the four GABA transporter subtypes led to the discovery of a subclass of a GAT2-selective compounds with acyl-substituted azaspiro[4.5]decane core. (C) 2015 Elsevier Ltd. All rights reserved.