3-(1,4-dioxaspiro[4,5]dec-6-yl)propan-1-ol | 62547-87-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(1,4-dioxaspiro[4,5]dec-6-yl)propan-1-ol
• 英文别名: 1,4-Dioxaspiro[4.5]decane-6-propanol；3-(1,4-dioxaspiro[4.5]decan-6-yl)propan-1-ol
• CAS: 62547-87-9
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: MMDXIPULJZAKKT-UHFFFAOYSA-N

物化性质

• 沸点：
  163-164 °C(Press: 20 Torr)
• 密度：
  1.0876 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1,4-dioxaspiro[4,5]dec-6-yl)propan-1-ol 在 盐酸 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 24.0h， 生成 3,4,5,6,7,8-hexahydro-2H-chromene
  参考文献：
  名称：

  Ozonolyse von Enolethern. 9. Synthese und Ozonolyse von 5,6,7,8-Tetrahydrochroman

  摘要：

  The regioselectivity of the transfer of three oxygens of ozone to the olefinic carbons of the rigid substituted enol ether 5,6,7,8-tetrahydrochroman (3) is proved by isolation of omega-caprinolactone 5 instead of an earlier claimed oxacyclode-canone 4.

  DOI：

  10.1002/prac.199533701118
• 作为产物：
  描述：

  6-allyl-1,4-dioxaspiro[4.5]decane 在 sodium hydroxide 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 双氧水 作用下， 生成 3-(1,4-dioxaspiro[4,5]dec-6-yl)propan-1-ol
  参考文献：
  名称：

  Ozonolyse von Enolethern. 9. Synthese und Ozonolyse von 5,6,7,8-Tetrahydrochroman

  摘要：

  The regioselectivity of the transfer of three oxygens of ozone to the olefinic carbons of the rigid substituted enol ether 5,6,7,8-tetrahydrochroman (3) is proved by isolation of omega-caprinolactone 5 instead of an earlier claimed oxacyclode-canone 4.

  DOI：

  10.1002/prac.199533701118

文献信息

• Preparation of Sixteen 3-Hydroxy-4- and 7-Hydroxy-1-hydrindanones and 3-Hydroxy-4- and 8-Hydroxy-1-hydroazulenones
  作者：Georgia G. Tsantali、John Dimtsas、Constantinos A. Tsoleridis、Ioannis M. Takakis

  DOI：10.1002/ejoc.200600639

  日期：2007.1

  3-Hydroxyoctahydro-4H-inden-4-ones and 7-hydroxyoctahydro-1H-inden-1-ones (1, 2 and 3, 4, respectively), as well as the homologous 3-hydroxyoctahydro-4(1H)-azulenones (5, 6) and 8-hydroxyoctahydro-1(2H)-azulenones (7, 8), were prepared diastereoselectively either from the precursor α,β-enones 9, 10, 11, and 12 or by an isoxazoline method. Unmasking of the isoxazolines 13i, 14i, and 14j with O3 proved

  3-Hydroxyoctahydro-4H-inden-4-ones 和 7-hydroxyoctahydro-1H-inden-1-ones（分别为 1, 2 和 3, 4），以及同源的 3-hydroxyoctahydro-4(1H)-azulenones (5, 6) 和 8-羟基八氢-1(2H)-azulenones (7, 8) 是从前体 α,β-烯酮 9、10、11 和 12 或通过异恶唑啉方法非对映选择性制备的。用 O3 暴露异恶唑啉 13i、14i 和 14j 证明比氢解更具立体选择性。在许多情况下，在将可差向异构的非对映异构体通过填充硅胶的柱子时观察到具有 100% 完整性的差向异构化，因此在大多数情况下，反式稠合的氢化茚酮提供顺式稠合的差向异构体，而顺式稠合的氢化茚酮形成反式。这些结果已被 AM1 理论计算证实，这表明这些氢化茚酮系统中的顺式融合差向异构体比转融合变体更
• Mitsunobu-type alkylation of p-toluenesulfonamide. A convenient new route to primary and secondary amines
  作者：Tetsuto Tsunoda、Hidetoshi Yamamoto、Kayo Goda、Shô Itô

  DOI：10.1016/0040-4039(96)00317-6

  日期：1996.4

  give N-substituted sulfonamides in excellent yields. The reaction can be applied to the synthesis of symmetrical and unsymmetrical N,N-disubstituted amides. When coupled with the desulfurization reactions, the reaction provides a new versatile synthetic route to primary and secondary amines from ammonia.

  对-甲苯磺酰胺，已知在Mitsunobu条件下会形成膦酰亚胺，已显示在氰基亚甲基三丁基膦烷的存在下被烷基化，从而以极好的收率得到N-取代的磺酰胺。该反应可以用于合成对称和不对称的N，N-二取代的酰胺。当与脱硫反应结合时，该反应提供了一条新的通用合成路线，可从氨中合成伯胺和仲胺。
• The Synthesis of Cycloalkenes by the IntramolecularWittig Reaction
  作者：Konrad B. Becker

  DOI：10.1002/hlca.19770600110

  日期：1977.1.26

  A simple synthesis of a series of bicyclo[m.n.0]-1-alkenes (m, n = 3,4,5) from 2-oxocycloalkanecarboxylates by the intramolecular Wittig reaction is reported (see p. 70–72). The spectral properties (IR., 1H-NMR. and 13C-NMR.) of these annulated trisubstituted olefins are discussed.

  据报道，通过分子内的Wittig反应由2-氧代环烷羧酸酯简单地合成了一系列双环[mn0] -1-烯烃（m，n = 3,4,5）（参见第70-72页）。讨论了这些环状三取代烯烃的光谱性质（IR，1 H-NMR和13 C-NMR）。
• Visible Light Initiated Photosensitized Electron Transfer Cyclizations of Aldehydes and Ketones to Tethered α,β-Unsaturated Esters:  Stereoselective Synthesis of Optically Pure <i>C</i>-Furanosides
  作者：Ganesh Pandey、Saumen Hajra、Manas K. Ghorai、K. Ravi Kumar

  DOI：10.1021/jo9702812

  日期：1997.8.1

  Photosensitized one-electron reductive activation of aldehydes/ketones tethered with activated olefins leads to efficient cyclization to give diastereoselective cycloalkanols in high yield. The activation is promoted by secondary and dark electron transfer from visible light (405 nm) initiated photosensitized electron transfer generated 9,10-dicyanoanthracene radical anion (DCA(.-)). The DCA(.-) is produced by electron transfer using either triphenylphosphine (Ph3P) as sacrificial electron donor (PS-A) or 1,5-dimethoxynaphthalene (DMN) as primary electron donor and ascorbic acid as sacrificial electron donor (PS-B), to light-absorbing DCA. The cyclization is suggested to involve ketyl radical intermediate. High trans diastereoselectivity is observed during the formation of cycloalkanols. This cyclization strategy is further extended for the stereoselective synthesis of optically pure C-furanoside (41), starting from naturally occuring L-tartaric acid. The stereochemistry of 41 is suggested based on the single-crystal X-ray diffraction data.
• Silver-Catalyzed 7<i>-exo-</i> dig Cyclization of Silylenolether-ynesulfonamides
  作者：Clément F. Heinrich、Indira Fabre、Laurence Miesch

  DOI：10.1002/anie.201510708

  日期：2016.4.18

  AbstractCyclization of silylenolether‐ynesulfonamides proceeds at ambient temperature under mild reaction conditions under silver catalysis. Bridged compounds were obtained exclusively through 7‐exo‐dig reactions. The protocol is applicable to a wide range of substrates, thus leading to azabicyclic frameworks.