(S*)-1-oxaspiro<4.4>nonan-6-one | 141411-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (S*)-1-oxaspiro<4.4>nonan-6-one
• 英文别名: (+/-)-1-oxaspiro[4.4]nonan-6-one；1-Oxaspiro[4.4]nonan-6-one；1-oxaspiro[4.4]nonan-9-one
• CAS: 141411-97-4
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: XKWJYHWZACPOAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S*)-1-oxaspiro<4.4>nonan-6-one 在 Dowex-50X₄-400 、 叔丁基锂 作用下， 以 二氯甲烷 为溶剂， 生成 (5R,6S)-1,7-Dioxa-dispiro[4.0.4.4]tetradecan-11-one
  参考文献：
  名称：

  Synthesis and molecular structure of belted spirocyclic tetrahydrofurans, a new class of preorganized hosts for cations

  摘要：

  The preparation and binding properties of spirocyclic tetrahydrofurans 7-11 are described. The condensation of cyclopentanone with 5-lithio-2,3-dihydrofuran (12) provided an alcohol which readily rearranged to ketone 14 under acidic conditions. ''Capping'' of the carbonyl group in 14 so as to generate a second spiro tetrahydrofuran subunit gave rise to 7 and 8. Starting with cyclobutanone, 2-fold ring expansion involving 12 provided the key reactions leading to 22 and 23, which were 'capped' as before. Crystal structure data are available for 9, 11, and 22. In addition, the variable-temperature NMR behavior of 7 and 10 was quantified by means of 2-D measurements. A detailed analysis is presented that shows the gauche effect to be of major importance in dictating the major conformation adopted by these ionophores. The binding properties of 7-11 have been assayed. Considerable variation was found, the efficiency being critically dependent upon the number of oxygen atoms, the relative stereochemistry of the C-O bonds, and the relative ease of conformational readjustment necessary to achieve proper organization around the oxophilic metal ion.

  DOI：

  10.1021/jo00040a041
• 作为产物：
  描述：

  1-(4-hydroxybut-1-yn-1-yl)cyclobutan-1-ol 在 silver hexafluoroantimonate 、 氯[2-(二叔丁基磷)二苯基]金 作用下， 以 1,4-二氧六环 为溶剂， 以65%的产率得到(S*)-1-oxaspiro<4.4>nonan-6-one
  参考文献：
  名称：

  通过串联水合和α-酮醇重排，金催化1-炔基环丁醇衍生物的扩环

  摘要：

  我们在本文中报道了1-炔基环丁醇衍生物的金催化的串联水合/α-酮醇重排，导致带有α-羟基取代的季中心的环戊酮。在水的存在下，金催化剂在炔基部分上的配位会触发水合反应，而不是直接的环扩环反应，随后空前的Au催化的α-酮醇重排。介绍了此方法的详细信息和范围。

  DOI：

  10.1016/j.tet.2012.03.018

文献信息

• 1-Oxaspiro[4.4]nonan-6-ones. Synthetic Access via Oxonium Ion Technology, Optical Resolution, and Conversion into Enantiopure Spirocyclic α,β-Butenolides
  作者：Leo A. Paquette、Dafydd R. Owen、Richard Todd Bibart、Christopher K. Seekamp、Alexandra L. Kahane、James C. Lanter、Miriam Alvarez Corral

  DOI：10.1021/jo010026o

  日期：2001.4.1

  A general approach to the synthesis of enantiomerically pure spirocyclic alpha,beta-butenolides is presented where the fundamental framework is rapidly elaborated by acid- or bromonium ion-induced rearrangement of the carbinol derived by addition of 2-lithio-4,5-dihydrofuran to cyclobutanone. Subsequent resolution of the resulting ketones by either sulfoximine or mandelate acetal technology has been

  提出了合成对映体纯的螺环α，β-丁烯内酯的一般方法，其中基本构架通过酸或溴离子诱导的甲醇的重排反应而迅速完善，该重排反应是通过向2-硫代-4,5-二氢呋喃中添加而得到的。环丁酮。通过硫代亚胺或扁桃酸缩醛技术对所得酮的后续拆分已得到有效应用。这些结构单元的可获得性又使得获得以17、35和38为代表的二氢呋喃的对映异构体以及诸如25和31的内酯以及目标标题化合物成为可能。早期中间体的互补还原提供了额外的优势，即可以按需获得α-和β-立体异构甲醇系列。
• Brønsted Acid Catalyzed Enantioselective Semipinacol Rearrangement for the Synthesis of Chiral Spiroethers
  作者：Qing-Wei Zhang、Chun-An Fan、Hai-Jun Zhang、Yong-Qiang Tu、Yu-Ming Zhao、Peiming Gu、Zhi-Min Chen

  DOI：10.1002/anie.200904565

  日期：2009.10.26

  A new twist: The catalytic asymmetric semipinacol rearrangement reaction of 2‐oxo allylic alcohols 1 in the presence of a catalytic amount of chiral phosphoric acid (R)‐2 a or its silver salt (R)‐2 b affords enantiomerically pure spiroethers 3.

  一个新的转折：2-氧代烯丙醇的催化不对称semipinacol重排反应1在手性磷酸（催化量存在- [R ）- 2或它的银盐（[R ）- 2 B，得到对映体纯spiroethers 3。
• 3,4-DIAMINO-3-CYCLOBUTENE-1,2-DIONE DERIVATIVES AS POTASSIUM CHANNEL OPENERS
  申请人：Lanter James C.

  公开号：US20070232689A1

  公开（公告）日：2007-10-04

  The present invention is directed to novel 3,4-diamino-3-cyclobutene-1,2-dione derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders related to potassium channel.

  本发明涉及新颖的3,4-二氨基-3-环丁烯-1,2-二酮衍生物，包含它们的药物组合物以及它们在治疗与钾通道相关的疾病中的应用。
• New Cyclohexadienone Derivatives: Preparation and Chiral Discrimination in High-Pressure Diels-Alder Cycloadditions
  作者：Marie-Elise Trân-Huu-Dâu、Rudolf Wartchow、Ekkehard Winterfeldt、Yung-Sing Wong

  DOI：10.1002/1521-3765(20010601)7:11<2349::aid-chem23490>3.0.co;2-c

  日期：2001.6.1

  A wide range of cyclohexadienones has been synthesised in order to study their reactivity and their regio- and stereoselectivity with the enantiopure diene 1 under high-pressure conditions. Computational investigations were used to point out some parameters which affect the reactivity in this high chiral discrimination process. In addition, the resulting [4+2] cycloadducts allowed the preparation of new polyfunctional cyclohexenone derivatives.
• Negri, Joanna T.; Rogers, Robin D.; Paquette, Leo A., Journal of the American Chemical Society, 1991, vol. 113, # 13, p. 5073 - 5075
  作者：Negri, Joanna T.、Rogers, Robin D.、Paquette, Leo A.

  DOI：——

  日期：——