1,6-dioxaspiro[4.5]decan-2-one | 4744-44-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-dioxaspiro[4.5]decan-2-one
• 英文别名: 1,6-Dioxaspiro<4.5>decan-2-one；1,10-dioxaspiro[4.5]decan-2-one
• CAS: 4744-44-9
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: YFVHVXQMVVESQB-UHFFFAOYSA-N

物化性质

• 沸点：
  137-140 °C(Press: 11 Torr)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,6-dioxaspiro[4.5]decan-2-one 在 camphor-10-sulfonic acid 、 二甲基二环氧乙烷 作用下， 生成 1,7-二氧杂螺[5.5]十一烷-3-酮
  参考文献：
  名称：

  A novel method for the synthesis of spiroketal systems. Synthesis of the pheromones of the common wasp and the olive fruit fly

  摘要：

  Total syntheses of the pheromones of the common wasp and the olive fruit fly were accomplished by a strategy in which the key transformation involved the cleavage of tetrahydrofuran with (tert-butyldimethyl-sily)manganese pentacarbonyl followed by sequential insertion of ethyl acrylate.

  DOI：

  10.1021/jo00010a005
• 作为产物：
  描述：

  四氢吡喃-2-甲醇 在 草酰氯 、 palladium 10% on activated carbon 、 C₂₄H₃₂FeN₆⁽²⁺⁾*2F₆Sb^(1-) 、 氢气 、 双氧水 、 二甲基亚砜 作用下， 以 二氯甲烷 、 水 、 异丙醇 、 乙腈 为溶剂， 反应 64.52h， 生成 1,6-dioxaspiro[4.5]decan-2-one
  参考文献：
  名称：

  Directed Metal (Oxo) Aliphatic C–H Hydroxylations: Overriding Substrate Bias

  摘要：

  The first general strategy for a directing effect on metal (oxo)-promoted C-H hydroxylations is described. Carboxylic acid moieties on the substrate overcome unfavorable electronic, steric, and stereoelectronic biases in C-H hydroxylations catalyzed by the non-heme iron complex Fe(PDP). In a demonstration of the power of this directing effect, C-H oxidation is diverted away from an electronically favored C-1 H abstraction/rearrangement pathway in the paclitaxel framework to enable installation of C-2 oxidation in the naturally occurring oxidation state and stereoconfiguration.

  DOI：

  10.1021/ja301685r

文献信息

• Cyclisation of alkynecarboxylic acids: a route to an oxaspirolactone
  作者：Makoto Yamamoto、Makoto Yoshitake、Kazutoshi Yamada

  DOI：10.1039/c39830000991

  日期：——

  Pent-4-yonic acid, in various alcohols, was cyclised in the presence of yellow mercury(II) oxide to 4,5-dihydro-5-alkoxy-5-methylfuran-2(3H)-ones; 8-hydroxyoct-4-yonic acid was also cyclised in dimethylformamide to 1,6-dioxaspiro[4.5]decan-2-one in good yield.

  在黄色醇（II）氧化物存在下，将五元醇中的戊-4-磺酸酸环化为4,5-二氢-5-烷氧基-5-甲基呋喃-2（3 H）-酮；还以高收率将8-羟基辛基-4-磺酸在二甲基甲酰胺中环化为1,6-二氧杂螺[4.5]癸-2-。
• Catalytic Carbonylative Spirolactonization of Hydroxycyclopropanols
  作者：Dexter C. Davis、Katherine L. Walker、Chunhua Hu、Richard N. Zare、Robert M. Waymouth、Mingji Dai

  DOI：10.1021/jacs.6b06573

  日期：2016.8.24

  four steps, respectively. The hydroxycyclopropanol substrates are readily available in one step via a Kulinkovich reaction of the corresponding lactones. Mechanistic studies utilizing high-resolution electrospray ionization mass spectrometry (ESI-MS) identified several key intermediates in the catalytic cycle, as well as those related to catalyst decomposition and competitive pathways.

  已开发出钯催化的羟基环丙醇级联羰基化螺内酯化反应，以有效合成许多具有重要治疗价值的复杂天然产物常见的氧杂螺内酯。这种新方法的温和反应条件、高原子经济性、广泛的底物范围和可扩展性在土耳其烟草天然产物 α-levantanolide 和 α-levantenolide 的两步和四步的便利全合成中得到了强调。羟基环丙醇底物可通过相应内酯的库林科维奇反应一步轻松获得。利用高分辨率电喷雾电离质谱 (ESI-MS) 的机理研究确定了催化循环中的几个关键中间体，以及与催化剂分解和竞争途径相关的中间体。
• Progress in the Synthesis of the Lituarines:  Stereocontrol in Sequential C−C Bond Formation on a Spirobutenolide Template
  作者：Jeremy Robertson、Jonathan W. P. Dallimore

  DOI：10.1021/ol0520018

  日期：2005.10.1

  [GRAPHICS]We describe elaboration of a tricyclic spirobutenolide corresponding to the C(7-18) tricyclic substructure common to lituarines A-C. Conjugate addition, to install the C(16) methyl, is followed by construction of the crucial C(18-19) bond by silyl enol ether addition to the derived spiroacetal C(18)-O oxonium ion. Esterification with a C(1-6) acid, and selective ozonolysis to release the C(23) carbonyl, complete the assembly of all the carbons present in the lituarine macrocyclic core.
• Regioselective opening of epoxides and ethers by (trialkylsilyl)manganese pentacarbonyl complexes. A general strategy for the synthesis of spiroketal lactone and cyclopentenone derivatives
  作者：Philip DeShong、Daniel R. Sidler

  DOI：10.1021/jo00255a051

  日期：1988.9
• FUKUDA H.; TAKEDA M.; SATO Y.; MITSUNOBU O., SYNTHESIS, 1979, NO 5, 368-370
  作者：FUKUDA H.、 TAKEDA M.、 SATO Y.、 MITSUNOBU O.

  DOI：——

  日期：——