(5R,7R)-7-Methyl-1,6-dioxaspiro<4.5>decane | 209248-22-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R,7R)-7-Methyl-1,6-dioxaspiro<4.5>decane
• 英文别名: (E)-(5R,7R)-(+)-7-Methyl-1,6-dioxaspiro[4.5]decane；(5R,7R)-(+)-7-methyl-1,6-dioxaspiro[4.5]decane；(5R,7R)-7-Methyl-1,6-dioxaspiro[4.5]decane
• CAS: 209248-22-6
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: XNNASGSBOJGKAZ-RKDXNWHRSA-N

物化性质

• 沸点：
  201.7±8.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 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

• 作为产物：
  描述：

  1-(tetrahydropyran-2-yloxy)non-8-en-4-one 在 W-Raney-Ni camphor-10-sulfonic acid 、 氢气 、 zinc dibromide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (5R,7R)-7-Methyl-1,6-dioxaspiro<4.5>decane
  参考文献：
  名称：

  Doherty, Annette M.; Ley, Steven V.; Lygo, Barry, Journal of the Chemical Society. Perkin transactions I, 1984, p. 1371 - 1378

  摘要：

  DOI：

文献信息

• Synthesis of Spiroacetal Pheromones via Metalated Hydrazones
  作者：Dieter Enders、Walter Dahmen、Eleonore Dederichs、Winfried Gatzweiler、Peter Weuster

  DOI：10.1055/s-1990-27080

  日期：——

  The synthesis of simple alkyl substituted spiroacetals by α,α′-alkylation of metalated acetone dimethylhydrazone with appropriate electrophiles and subsequent acid catalyzed cleavage and ring closure of the products is described.

  通过合适的亲电试剂与金属化丙酮二甲基脲的α,α′-烷基化反应，随后进行酸催化的断裂和环化闭合，描述了简单烷基取代螺缩醛的合成方法。
• 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。
• Synthesis of optically active 2s-, and 7s-methyl-1.6-dioxa-spiro[4.5] decane, the pheromone components of Paravespula vulgaris (L.), from S-ethyl lactate.
  作者：K. Hintzer、R. Weber、V. Schurig

  DOI：10.1016/0040-4039(81)80039-1

  日期：1981.1

  (−)-2S, 5RS-1 and (−]-7S, 5S-2 are obtained from S-ethyl lactate 4 and their absolute configuration is thus directly correlated. Accurate enantiomeric compositions of intermediates and products were measured by complexation gas chromatography on nickel-, and manganese-bis-3-heptafluorobutyryl-1R-camphorate, 3. It could be conclusively established that the syntheses proceed with a high degree of preservation

  （-）-2S，5RS-1和（-]-7S，5S-2是由乳酸S-乙酯4得到的，因此它们的绝对构型直接相关，中间体和产物的精确对映体组成通过络合气相色谱法测定。镍-和锰-双-3-3七氟丁酰-1R-樟脑膦酸酯3.可以确定地确定合成过程在高度保留构型的情况下进行。
• 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。
• Spiroacetals and Other Venom Constituents as Potential Wasp Attractants
  作者：Roderick J. Weston、Anthony D. Woolhouse、Eric B. Spurr、Richard J. Harris、D. Max Suckling

  DOI：10.1023/b:joec.0000006396.55680.b6

  日期：1997.3

  The major volatile spiroacetals from the venom of both the common wasp, Vespula vulgaris and the German wasp V. germanica, viz. 7-methyl-1,6-dioxaspiro[4,5]decane and 7-ethyl-2-methyl-1,6-dioxaspiro[4,5]decane, respectively, were synthesized by known methods. These acetals, along with N-isopentylacetamide (the major volatile amide from wasp venom), 2-heptanone (a honeybee pheromone), 2-methyl-3-buten-2-ol (a component of hornet venom), cuticle wax from V. vulgaris, and venom sacs from both wasp species were assayed by EAG and olfactory bioassay for attractancy to V. vulgaris workers. Antennal responses to all test chemicals were recorded. Acetal isomers (+/-)-2 and (+/-)-3, N-isopentylacetamide, and 2-heptanone were attractive to V. vulgaris workers at levels of <1 mu mol. Greater quantities of the same compounds were repellent to V. vulgaris workers.