3-phenyl-1,5-dioxaspiro[3.2]hexane | 244023-84-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-phenyl-1,5-dioxaspiro[3.2]hexane
• 英文别名: 4-phenyl-1,6-dioxaspiro[2.3]hexane
• CAS: 244023-84-5
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: QPANAOBWSJADFR-UHFFFAOYSA-N

物化性质

• 沸点：
  269.8±25.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenyl-1,5-dioxaspiro[3.2]hexane 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以61%的产率得到1,4-dihydroxy-3-phenylbutan-2-one
  参考文献：
  名称：

  Ring Opening of 1,5-Dioxaspiro[3.2]hexanes:  Selective Preparation of α-Heterofunctionalized-β‘-hydroxy Ketones or 2,2-Disubstituted Oxetanes

  摘要：

  [GRAPHICS]2-Methyleneoxetanes have been converted into 1,5 dioxaspiro[3.2]hexanes with dimethyldioxirane. Reaction of the dioxaspirohexanes with a range of heteroatom nucleophiles, hydride donors, or organoaluminum reagents was successful under neutral or mild conditions, affording, selectively, polyfunctionalized ketones or 2,2 disubstituted oxetanes.

  DOI：

  10.1021/ol990039c
• 作为产物：
  描述：

  2-methylene-3-phenyloxetane 在 二甲基二环氧乙烷 作用下， 以99%的产率得到3-phenyl-1,5-dioxaspiro[3.2]hexane
  参考文献：
  名称：

  The First General Synthesis of 1,5-Dioxaspiro[3.2]hexanes

  摘要：

  DOI：

  10.1021/jo981309s

文献信息

• Directed Ring-Opening of 1,5-Dioxaspiro[3.2]hexanes:  Selective Formation of 2,2-Disubstituted Oxetanes
  作者：Rosa Taboada、Grace G. Ordonio、Albert J. Ndakala、Amy R. Howell、Paul R. Rablen

  DOI：10.1021/jo0206465

  日期：2003.2.1

  nucleophiles provide 2,2-disubstituted oxetanes. Herein, the results of reactions of 3-phenyl-1,5-dioxaspiro[3.2]hexane with a variety of nitrogen-containing heteroaromatic bases are reported. There appears to be a correlation between the pK(a) of the nucleophile and the reaction outcome with more acidic nucleophiles providing 2,2-disubstituted oxetanes. Moreover, the mode of ring opening can be directed toward

  1,5-二氧杂螺并[3.2]己烷与许多杂原子亲核试剂发生开环反应，以提供α-取代的β'-羟基酮。然而，某些路易斯酸性亲核试剂提供2，2-二取代的氧杂环丁烷。在此，报道了3-苯基-1，5-二氧杂螺[3.2]己烷与各种含氮杂芳族碱的反应结果。亲核试剂的pK（a）与反应结果之间存在相关性，酸性更高的亲核试剂可提供2,2-二取代的氧杂环丁烷。此外，可通过添加路易斯酸将开环的方式导向取代的氧杂环丁烷。通过使用从头算分子轨道方法计算各种可能的反应途径的势能表面上的固定点，可以使这些结果合理化。
• [EN] HETEROCYCLYL-SUBSTITUTED OXETANES FOR THE TREATMENT OF PROLIFERATIVE OR INFECTIOUS DISEASES<br/>[FR] OXETANES A SUBSTITUTION HETEROCYCLYLE PERMETTANT DE TRAITER DES MALADIES PROLIFERATIVES OU INFECTIEUSES
  申请人：UNIV CONNECTICUT

  公开号：WO2005051944A1

  公开（公告）日：2005-06-09

  Oxetane-containing nucleosides, particularly non-reducing psiconucleoside oxetanes (1) are described herein. Therapeutic application of these oxetane compounds toward the treatment of nucleoside analog related disorders such as disorders involving cellular proliferation and infection are also described.

  本文描述了含氧杂环氧乙烷的核苷类化合物，尤其是非还原型偏心核苷类氧杂环氧乙烷（1）。还描述了这些氧杂环氧乙烷化合物在治疗与核苷类似物相关的疾病，如涉及细胞增殖和感染的疾病方面的治疗应用。
• Substituted oxetanes, method of making, and method of use thereof
  申请人：Howell R. Amy

  公开号：US20050215568A1

  公开（公告）日：2005-09-29

  Oxetane-containing nucleosides, particularly non-reducing psiconucleoside oxetanes are described herein. Therapeutic application of these oxetane compounds toward the treatment of nucleoside analog related disorders such as disorders involving cellular proliferation and infection are also described.

  本文描述了含有氧杂环丙烷的核苷类化合物，特别是非还原型偏心核苷类氧杂环丙烷。还描述了这些氧杂环丙烷化合物在治疗与核苷类似物相关的疾病，例如涉及细胞增殖和感染的疾病方面的治疗应用。
• SUBSTITUTED OXETANES, METHOD OF MAKING, AND METHOD OF USE THEREOF
  申请人：Howell Amy R.

  公开号：US20080139566A1

  公开（公告）日：2008-06-12

  Oxetane-containing nucleosides, particularly non-reducing psiconucleoside oxetanes are described herein. Therapeutic application of these oxetane compounds toward the treatment of nucleoside analog related disorders such as disorders involving cellular proliferation and infection are also described.

  本文描述了含有氧杂环丙烷的核苷，特别是非还原的偏心核苷氧杂环丙烷。还描述了这些氧杂环丙烷化合物在治疗与核苷类似物相关的疾病，例如涉及细胞增殖和感染的疾病的治疗应用。
• Synthesis of <i>epi</i>-Oxetin via a Serine-Derived 2-Methyleneoxetane
  作者：Marisa L. Blauvelt、Amy R. Howell

  DOI：10.1021/jo7018762

  日期：2008.1.1

  [GRAPHICS]The unique reactivity of 2-methyleneoxetanes and 1,5-dioxaspiro[3.2]hexanes has been exploited for the synthesis of epi-oxetin (26), an oxetane-containing beta-amino acid. While the preparation of the natural product oxetin (1) was the original goal, the unexpected diastereoselectivity of an precedented reduction provided the epi-oxetin framework. The methodology described herein should be amenable for the preparation of oxetin with a change in nitrogen protection.