1,6-二氧杂-螺[4.5]癸烷 | 177-23-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,6-二氧杂-螺[4.5]癸烷
• 英文名称: 1,6-dioxa-spiro<4.5>decane
• 英文别名: Dioxa-1,6 spiro<4.5>decane；1,6-Dioxaspiro<4.5>decane；1,6-dioxaspiro<4,5>decane；1,6-Dioxaspiro<4.5>decan；1,6-dioxaspiro[4.5]decane；1,6-dioxa-spiro[4.5]decane；1,10-dioxaspiro[4.5]decane
• CAS: 177-23-1
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: HZWQUQZFYLDNPC-UHFFFAOYSA-N

物化性质

• 沸点：
  172-173 °C(Press: 750 Torr)
• 密度：
  1.0197 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1,6-二氧杂-螺[4.5]癸烷 在 potassium tert-butylate 、 溴 、 calcium carbonate 作用下， 以 四氯化碳 、 二甲基亚砜 为溶剂， 生成 1,6-Dioxaspiro<4.5>dec-9-ene
  参考文献：
  名称：

  .alpha.-Bromo spiroketals: stereochemistry and elimination reactions

  摘要：

  The simple spiroketals, 1,6-dioxaspiro[4.4]nonane (2), 1,6-dioxaspiro[4.5]decane (5), 1,7-dioxaspiro[5.5]undecane (6), and (E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane (7), have been brominated by bromine in carbon tetrachloride/calcium carbonate or acetic acid, and a number of mono-, di-, and tribromo derivatives have been characterized. The relative stereochemistries have been established by correlated H-1 and C-13 NMR spectroscopy and X-ray crystal structure determinations. Dehydrobromination with potassium tert-butoxide in either dimethyl sulfoxide or tetrahydrofuran is facile for the axial monobromides, although both axial and equatorial bromides derived from 1,6-dioxaspiro[4.5]decane (5) and 1,7-dioxaspiro[5.5]undecane (6) dehydrobrominate to provide 1,6-dioxaspiro[4.5]dec-9-ene (35) and 1,7-dioxaspiro[5.5]undec-4-ene (26), respectively. Hydration of these readily acquired alkenes furnishes the corresponding 9- and 4-ols, respectively, with the latter being components of the rectal glandular secretion of Bactrocera oleae (olive fly), Bactrocera cacuminatus, and Bactrocera distincta. These studies indicate that alpha-bromination of suitable spiroketals may be a viable later step in the synthesis of alpha-bromine-containing spiroketal metabolites such as obtusin and neoobtusin.

  DOI：

  10.1021/jo00061a025
• 作为产物：
  描述：

  (Z)-oct-4-ene-1,8-diol 在 N-溴代丁二酰亚胺(NBS) 、 potassium hydride 作用下， 以 四氯化碳 、 乙二醇二甲醚 为溶剂， 反应 14.0h， 生成 1,6-二氧杂-螺[4.5]癸烷
  参考文献：
  名称：

  Synthesis of threo- and erythro-bis(2,2′-tetrahydrofuran). A novel serendipitous synthesis of a spiroketal

  摘要：

  Racemic threo-bis(2,2'-tetrahydrofuran) and meso-erythro-bis(2,2'-tetrahydrofuran) have been prepared by stereochemically unambiguous routes. Treatment of 2-(1'-bromo-4'-hydroxybutyl)-tetrahydrofuran with base or silver(I) tetrafluoroborate effected cyclisation to 1,6-dioxa-spiro[4.5]decane. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00173-2

文献信息

• Pheromonsynthesen ‐ Modellreaktionen zur Synthese von Polyether‐Antibiotika
  作者：Robert E. Ireland、Dieter Häbich

  DOI：10.1002/cber.19811140419

  日期：1981.4

  Schema zur Synthese von Spiroketalen wird vorgestellt. Die Hetero-Diels-Alder-Reaktion zwischen einem exocyclischen Enolether 5 und einer α,β-ungesättigten Carbonylverbindung führt zu Spiroalkenen 6. Diese lassen sich durch oxidative Ringkontraktion oder Reduktion zu 7 oder 8, den gemeinsamen Strukturelementen verschiedener Polyether-Antibiotika und Insekteninhaltsstoffe, umsetzen. Modellreaktionen zu

  Ein allgemeines，konvergentes Schema zur Synthese von Spiroketalen wird vorgestellt。Die Hetero-Diels-Alder-Reaktion zwischen einem exocyclischen Enolether 5和einerα ，β-ungesättigtenCarbonylverbindungführtzu Spiroalkenen 6。Diese lassen sich durch氧化Ringkontraktion oder Reduktion zu 7 oder 8，geminsinsamen Strukturelementen verschiedener聚醚-Antibiotika和Insekteninhaltsstoffe，umsetzen。型号为Sequenz的双模，2-甲基四氢吡
• Alkylation reactions of anions derived from 2-benzenesulphonyl tetrahydropyran and their application to spiroketal syntiesis
  作者：Steven V. Ley、Barry Lygo、Francine Sternfeld、Anne Wonnacott

  DOI：10.1016/s0040-4020(01)87660-2

  日期：1986.1

  Deprotonation of (1) follwed by alkylation with carbonyl compounds or halides gave cyclic enol ether addition products by spontaneous elimination of benzenesulphinic acid. Interception of the initial addition products with aldehydes by reductive desulphonylation to give alkylated tetrahydropyran derivatives proeeeded in moderate yield using sodium naphthalenide. Several of the cystic enol ether addition products

  3,4-二氢-2H-吡喃或2-甲氧基四氢吡喃与苯磺酸反应生成2-苯磺酰基四氢吡喃（1）。（1）通过与羰基化合物或卤化物进行烷基化反应进行脱质子化，通过自发消除生成环状烯醇醚加成产物苯磺酸。通过萘二甲磺酸钠的还原性去磺酰化作用，将起始的加成产物与醛类截获，以得到中等收率的烷基化四氢吡喃衍生物。几个囊性烯醇醚加成产物进一步转化成spiroketals包括来自天然产物的信息素的合成和。
• Wittig and horner-wittig coupling reactions of 2-substituted cyclic ethers and their application to spiroketal synthesis
  作者：Steven V Ley、Barry Lygo、Helen M. Organ、Anne Wonnacott

  DOI：10.1016/s0040-4020(01)91403-6

  日期：1985.1

  Wittig and Horner-Wittig coupling reactions of tetrahydropyran or tetrahydrofuran 2-triphenylphosphonium salts or 2-diphenylphosphine oxides with aldehydes and lactols affords good yields of the corresponding enol ethers. In selected examples these enol ether products may be further converted to spiroketals some of which are natural pheromones derived from Dacus oleae and Paravespula vulgaris.

  四氢吡喃或四氢呋喃2-三苯基phosph盐或2-二苯基膦氧化物与醛和乳糖醇的Wittig和Horner-Wittig偶联反应提供了良好的相应烯醇醚产率。在选定的实例中，这些烯醇醚产物可以进一步转化为螺环酮，其中一些是得自油茶和寻常型草的天然信息素。
• Spiro compounds for treatment of inflammatory disorders
  申请人：Weingarten M. David

  公开号：US20080280974A1

  公开（公告）日：2008-11-13

  Provided are compounds, pharmaceutical compositions and methods of treatment or prophylaxis of an inflammatory condition, in particular asthma. The compounds are of the general Formula I, or a pharmaceutically acceptable salt, ester, prodrug or derivative thereof: wherein Y, Z and R 1 -R 12 are defined herein.

  提供了化合物、药物组合物以及治疗或预防炎症性疾病，特别是哮喘的方法。这些化合物属于一般的I式，或其药用可接受的盐、酯、前药或衍生物：其中Y、Z和R1-R12在此处定义。
• Syntheses photochimiques de dioxa-1,6 spiro[4.5] decanes pheromones de paravespula vulgaris L
  作者：Tomasz Koźluk、Louis Cottier、Gérard Descotes

  DOI：10.1016/s0040-4020(01)97936-0

  日期：——

  A general approach to 1-6 dioxa[4.5]spirodecanes is presented and applied to the total synthesis of one pheromone of Paravespula vulgaris L.

  提出了一种一般的方法，对1-6个二恶英[4.5]螺旋十二烷进行了研究，并将其应用于杂草副生菜的一种信息素的全合成。

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