(5S,7S)-7-methyl-1,6-dioxaspiro[4.5]decane | 77715-03-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,7S)-7-methyl-1,6-dioxaspiro[4.5]decane
• CAS: 77715-03-8
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: XNNASGSBOJGKAZ-IUCAKERBSA-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：

  5-Nonyn-4-one, 1-hydroxy-8-(phenylmethoxy)-, (8S)- 在 palladium on activated charcoal 氢气 、 盐酸 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 24.08h， 以62%的产率得到(5S,7S)-7-methyl-1,6-dioxaspiro[4.5]decane
  参考文献：
  名称：

  Alkynyltrifluoroborates as Versatile Tools in Organic Synthesis:  A New Route to Spiroketals

  摘要：

  A simple and efficient two-step approach to spiroketals is described. Key steps include the preparation of functionalized hydroxyl alpha-alkynones by ring-opening reactions of lactones with lithium alkynyltrifluoroborates followed by a palladium-catalyzed hydrogenation/spirocyclization of the prespiroketal intermediate.

  DOI：

  10.1021/ol047987k

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。
• 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。
• Verfahren zum Anlocken von kambiophagen, xylophagen und/oder myzetophagen Insekten
  申请人：Flügel GmbH

  公开号：EP2878198A1

  公开（公告）日：2015-06-03

  Ein Verfahren zum Anlocken von kambiophagen, xylophagen und/oder myzetophagen Insekten umfasst die Schritte: - zumindest teilweises Freisetzen zumindest eines Teils einer Lockstoffzusammensetzung aus einem Behälter, wodurch die Insekten zum Ort der Freisetzung angelockt werden; - Fangen der angelockten Insekten; wobei die Lockstoffzusammensetzung eine Verbindung gemäß der folgenden allgemeinen Formel umfasst: wobei X und Y gemeinsam für: stehen und wobei R1, R2, R3, R4, R5, R6, R7, R8 und R9 unabhängig voneinander für Wasserstoff, verzweigtes oder unverzweigtes Alkyl, verzweigtes oder unverzweigtes Alkenyl, oder substituiertes oder unsubstituiertes Aryl stehen. Bevorzugt ist Rosenoxid. Die Erfindung betrifft weiterhin die Verwendung solcher Verbindungen als Lockstoffe und diese enthaltende Lockstoffgemische.

  一种吸引噬木、噬木和/或噬真菌昆虫的方法，包括以下步骤 - 从容器中至少部分释放引诱剂组合物，从而将昆虫吸引到释放地点； - 捕获被吸引的昆虫； 其中引诱剂组合物包括符合以下通式的化合物： 其中 X 和 Y 共同代表 其中 R1、R2、R3、R4、R5、R6、R7、R8 和 R9 独立地代表氢、支链或未支链烷基、支链或未支链烯基或取代或未取代芳基。优选氧化玫瑰。本发明还涉及将此类化合物用作引诱剂和含有它们的引诱剂混合物。
• Lipase mediated resolution of 1,3-butanediol derivatives: chiral building blocks for pheromone enantiosynthesis. Part 3
  作者：Isidoro Izquierdo、Marı́a T. Plaza、Miguel Rodrı́guez、Juan A. Tamayo、Alicia Martos

  DOI：10.1016/s0957-4166(01)00038-6

  日期：2001.2

  (R,S)-1,3-butanediol 5 was kinetically resolved by enzymatic acetylation with vinyl acetate under the presence of Chirazyme (TM) L-2, c-f, yielding (S)-1-O-acetyl-1,3-hydroxybutane 6 and (R)-1,3-di-O-acetyl-1,3-butanediol 7 with enantiomeric excesses of 91%, (E=67.3). Compounds 6 and 7 were easily transformed into the corresponding (S)-3-O-(2-methoxyethoxymethyl)-3-hydroxybutanal 10 and (R)-3-benzyloxybutanal 19, through a protection-deprotection and functional group interchange methodology. Subsequent reaction of 10 and 19 with 3-(methoxycarbonlypropionyl-methylene)triphenylphosphorane afforded methyl (E,S)-8-O-(2-methoxyethoxymethyl)-4-oxo-5-nonenoate 12 and (E,R)-8-benzyl-oxy-4-oxo-5-nonenoate 20. The alkenes 19 and 20 were then catalytically hydrogenated to the corresponding saturated eaters 13 and 21. Treatment of 13 and 21 with 1,2-ethanedithiol/F3B . OEt2 afforded dithioketals 14 and 22, which were respectively reduced to (S)-1,8-dihydroxy-4-nonanone ethylidenedithioketal 15 and (R)-8-O-benzyl-1,8-dihydroxy-4-nonanone ethylidenedithioketal 23. Finally, deprotection of 15 by catalytic hydrogenation under acidic conditions gave the expected (5S,7S)-(-)-7-methy1-1,6-dioxaspiro[4.5]decane 1. The (5R,7R)-(+)-1 enantiomer was analogously prepared fi om 23. Both compounds were formed by this procedure with an e.e. of 91%. (C) 2001 Elsevier Science Ltd. All rights reserved.
• S-(+)-5-(Phenylthio)-2-pentanol and S-(+)-4-(Phenylthio)-2-butanol: Readily Prepared, Useful Additions to the Chirality Pool. Highly Enantioselective Syntheses of Naturally Occurring Spiroketal Pheromones
  作者：Hong Liu、Theodore Cohen

  DOI：10.1021/jo00112a025

  日期：1995.4

  The new chirons (S)-4-(phenylthio)-2-butanol (4) and (S)-5-(phenylthio)-2-pentanol (3) have been prepared efficiently in high enantiomeric excess by enzymatic reduction of the corresponding readily available ketones. Using the latter as a chiral building block, the highly optically enriched insect pheromonal components (5S,7S)-7-methyl-1,6-dioxaspiro[4.5]decane (7), (2S,6R)-2-methyl-1,7-dioxaspiro[5.5]undecane (8), and (2S,6R)-2-methyl-1,7-dioxaspiro[5.6]dodecane (9) have been synthesized in one pot by sequential deprotonation, reductive lithiation, transmetalation with cerium(III) chloride, treatment with lactones, and acidification.