5,5-dimethoxy-hexanal | 1152234-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5-dimethoxy-hexanal
• 英文别名: 5,5-Dimethoxyhexanal；5,5-dimethoxyhexanal
• CAS: 1152234-42-8
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: ONHXMKAVAMDZCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• 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：

  5,5-dimethoxy-hexanal 在 咪唑 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 C₃₀H₄₄O₄Si
  参考文献：
  名称：

  Lewis Acid Catalyzed Intramolecular Condensation of Ynol Ether-Acetals. Synthesis of Alkoxycycloalkene Carboxylates

  摘要：

  Treatment of ynol ether-tethered dialkyl acetals with catalytic quantities of scandium triflate in CH3CN gives rise to five-, six-, and seven-membered alkoxycycloalkene carboxylates in good to excellent yields. Tri- and tetrasubstituted carbocyclic and heterocyclic alkenes may be formed by this method, and the products obtained may serve as useful intermediates for natural product synthesis.

  DOI：

  10.1021/ol303026v
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 5,5-dimethoxy-hexanal
  参考文献：
  名称：

  Lewis Acid Catalyzed Intramolecular Condensation of Ynol Ether-Acetals. Synthesis of Alkoxycycloalkene Carboxylates

  摘要：

  Treatment of ynol ether-tethered dialkyl acetals with catalytic quantities of scandium triflate in CH3CN gives rise to five-, six-, and seven-membered alkoxycycloalkene carboxylates in good to excellent yields. Tri- and tetrasubstituted carbocyclic and heterocyclic alkenes may be formed by this method, and the products obtained may serve as useful intermediates for natural product synthesis.

  DOI：

  10.1021/ol303026v

文献信息

• Iminium ion cascade reactions: stereoselective synthesis of quinolizidines and indolizidines
  作者：Shawn M. Amorde、Ivan T. Jewett、Stephen F. Martin

  DOI：10.1016/j.tet.2008.10.074

  日期：2009.4

  A novel iminium ion cascade reaction has been developed that allows for the stereoselective synthesis of a variety of substituted aza-fused bicycles. The combination of amino allylsilanes and aldehydes (or ketones) was used to synthesize a number of quinolizidines and indolizidines in a one-pot reaction sequence. This technology has been used to effect the facile syntheses of several indolizidine and

  已经开发了一种新型亚胺离子级联反应，可以立体选择性地合成各种取代的氮杂融合双环。氨基烯丙基硅烷和醛（或酮）的组合被用于在一锅反应序列中合成许多喹唑西啶和吲哚里西啶。该技术已被用于实现几种吲哚里西啶和喹诺西啶天然产物的简便合成，包括 (±)-epilupinine、(±)-tashiromine 和 (-)-epimyrtine。已经检查了底物范围，改变氨基烯丙基硅烷（伯、仲和共轭）和羰基化合物（醛和酮）的类型，以提供各种稠环结构。改变选择的组分允许在核心结构的不同位置包含合成有用的官能团。
• A Single-Flask Synthesis of Morita–Baylis–Hillman Adducts from Ethoxyacetylene and Carbonyl Compounds: Synthesis of Subamolides D and E
  作者：Kevin Ng、Thomas G. Minehan

  DOI：10.1021/acs.orglett.6b01772

  日期：2016.8.19

  keto/aldehyde acetals (X = OMe) followed by the addition of a Lewis acid leads to five-, six-, and seven-membered hydroxycycloalkene carboxyates. The utility of this method is demonstrated in the synthesis of the α-alkylidene lactone natural products subamolide D and E.

  用醛和/或酮（2和4）和BF 3 ·OEt 2顺序处理（乙氧基乙炔基）锂可产生β-羟基烯酸酯5，总收率良好。类似地，1（M = Li）和二羰基化合物6（X = O）或酮/醛缩醛（X = OMe）的组合，然后添加路易斯酸，会生成五元，六元和七元羟基环烯羧酸盐。该方法的实用性在合成α-亚烷基内酯天然产物亚磺酰胺D和E中得到了证明。
• Lewis Acid Catalyzed Intramolecular Condensation of Ynol Ether-Acetals. Synthesis of Alkoxycycloalkene Carboxylates
  作者：Vincent Tran、Thomas G. Minehan

  DOI：10.1021/ol303026v

  日期：2012.12.7

  Treatment of ynol ether-tethered dialkyl acetals with catalytic quantities of scandium triflate in CH3CN gives rise to five-, six-, and seven-membered alkoxycycloalkene carboxylates in good to excellent yields. Tri- and tetrasubstituted carbocyclic and heterocyclic alkenes may be formed by this method, and the products obtained may serve as useful intermediates for natural product synthesis.