3-(1,4-dioxaspiro[4.4]non-6-yl)propionic acid methyl ester | 194283-89-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(1,4-dioxaspiro[4.4]non-6-yl)propionic acid methyl ester
• 英文别名: Methyl 3-(2,2-ethylenedioxycyclopentan-1-yl)propionate；methyl 3-(1,4-dioxaspiro[4.4]nonan-9-yl)propanoate
• CAS: 194283-89-1
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: WCGKYJFCQZJMFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1,4-dioxaspiro[4.4]non-6-yl)propionic acid methyl ester 在 氢氧化钾 、 lithium aluminium tetrahydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 26.5h， 生成 benzyl-[3-(1,4-dioxaspiro[4.4]non-6-yl)propyl]amine
  参考文献：
  名称：

  通过 Bruylants 反应取代角取代的八氢吲哚，十氢喹啉，八氢吡咯烷酮和八氢环戊五烯[b]吡咯

  摘要：

  通过标准方法将容易获得的环烷酰基乙酸和丙酸酯转化为相应的胺。这些反过来又提供了有效的环状α-氨基腈的途径，使之与一系列 格氏 试剂反应，产生立体选择性的 顺式 构型标题化合物。研究了这条路线的范围和局限性。通过X射线晶体学和NMR光谱法实现立体化学分配。

  DOI：

  10.1007/s00706-003-0136-8
• 作为产物：
  描述：

  methyl 3-(2-oxo-cyclopentyl)propanoate 、 乙二醇 在 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 反应 5.0h， 以99%的产率得到3-(1,4-dioxaspiro[4.4]non-6-yl)propionic acid methyl ester
  参考文献：
  名称：

  通过 Bruylants 反应取代角取代的八氢吲哚，十氢喹啉，八氢吡咯烷酮和八氢环戊五烯[b]吡咯

  摘要：

  通过标准方法将容易获得的环烷酰基乙酸和丙酸酯转化为相应的胺。这些反过来又提供了有效的环状α-氨基腈的途径，使之与一系列 格氏 试剂反应，产生立体选择性的 顺式 构型标题化合物。研究了这条路线的范围和局限性。通过X射线晶体学和NMR光谱法实现立体化学分配。

  DOI：

  10.1007/s00706-003-0136-8

文献信息

• Rhodium(II)-carbenoid C–H insertion reactions in the synthesis of α,β′-dioxospirane systems
  作者：Pompiliu S. Aburel、Christian Rømming、Kjell Undheim

  DOI：10.1039/b100179p

  日期：——

  Spiro[4.4]nonane-, spiro[4.5]decane- and spiro[4.6]undecane-α,β′-diones have been prepared from 1-diazo-4-(2,2-ethylenedioxycycloalkan-1-yl)butan-2-one intermediates by Rh2(OAc)4- and Rh2(TPA)4-catalyzed C–H insertions. Competitive insertions also gave trans-bicyclic derivatives. The relative stereochemistry in bicyclic derivatives has been determined by single crystal X-ray analyses.

  通过 Rh2(OAc)4- 和 Rh2(TPA)4- 催化的 CâH 插入反应，从 1-重氮-4-(2,2-亚乙二氧基环烷-1-基)丁-2-酮中间体制备了螺[4.4]壬烷、螺[4.5]癸烷和螺[4.6]十一烷δ,δ²â²-二酮。竞争性插入也产生了反式双环衍生物。通过单晶 X 射线分析，确定了双环衍生物的相对立体化学结构。
• Visible Light Initiated Photosensitized Electron Transfer Cyclizations of Aldehydes and Ketones to Tethered α,β-Unsaturated Esters:  Stereoselective Synthesis of Optically Pure <i>C</i>-Furanosides
  作者：Ganesh Pandey、Saumen Hajra、Manas K. Ghorai、K. Ravi Kumar

  DOI：10.1021/jo9702812

  日期：1997.8.1

  Photosensitized one-electron reductive activation of aldehydes/ketones tethered with activated olefins leads to efficient cyclization to give diastereoselective cycloalkanols in high yield. The activation is promoted by secondary and dark electron transfer from visible light (405 nm) initiated photosensitized electron transfer generated 9,10-dicyanoanthracene radical anion (DCA(.-)). The DCA(.-) is produced by electron transfer using either triphenylphosphine (Ph3P) as sacrificial electron donor (PS-A) or 1,5-dimethoxynaphthalene (DMN) as primary electron donor and ascorbic acid as sacrificial electron donor (PS-B), to light-absorbing DCA. The cyclization is suggested to involve ketyl radical intermediate. High trans diastereoselectivity is observed during the formation of cycloalkanols. This cyclization strategy is further extended for the stereoselective synthesis of optically pure C-furanoside (41), starting from naturally occuring L-tartaric acid. The stereochemistry of 41 is suggested based on the single-crystal X-ray diffraction data.
• Angularly Substituted Octahydroindoles, Decahydroquinolines, Octahydropyrindines, and Octahydrocyclopenta[b]pyrroles by Bruylants Reaction
  作者：Eberhard Reimann、Christian Ettmayr、Kurt Polborn

  DOI：10.1007/s00706-003-0136-8

  日期：2004.5.1

  The easily available cycloalkanoyl acetic- and propionic acid esters are transformed to the corresponding amines by standard procedures. These in turn provided an efficient access to cyclic α-aminonitriles, which were reacted with a series of Grignard reagents yielding stereoselectively the cis -configured title compounds; the scope and limitation of this route were investigated. The stereochemical

  通过标准方法将容易获得的环烷酰基乙酸和丙酸酯转化为相应的胺。这些反过来又提供了有效的环状α-氨基腈的途径，使之与一系列 格氏 试剂反应，产生立体选择性的 顺式 构型标题化合物。研究了这条路线的范围和局限性。通过X射线晶体学和NMR光谱法实现立体化学分配。