5-((2-methoxyethoxy)methoxy)pent-1-yne | 98076-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-((2-methoxyethoxy)methoxy)pent-1-yne
• 英文别名: 5-(2-methoxyethoxymethoxy)pent-1-yne；5-(methoxyethoxymethoxy)-pent-1-yne；6,8,11-trioxa-1-dodecyne
• CAS: 98076-86-9
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: QLSGWCFHUKDBTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-((2-methoxyethoxy)methoxy)pent-1-yne 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 3-ethyl-2-{3-[(2-methoxyethoxy)methoxy]propyl}-4,5-diphenyl-1H-pyrrole
  参考文献：
  名称：

  Copper-Catalyzed Vinylation of Hydrazides. A Regioselective Entry to Highly Substituted Pyrroles

  摘要：

  A modular route to highly substituted pyrroles has been developed. This transformation consists of two sequential copper-catalyzed vinylations of bis-Boc-hydrazine followed by thermal rearrangement/cyclization. A wide variety of functionalized pyrroles can be prepared in a selective manner from simple and easily accessible precursors.

  DOI：

  10.1021/ol062978s
• 作为产物：
  描述：

  [5-(2-methoxy-ethoxymethoxy)-pent-1-ynyl]-trimethyl-silane 在 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 以98%的产率得到5-((2-methoxyethoxy)methoxy)pent-1-yne
  参考文献：
  名称：

  A chemoselective deprotection of trimethylsilyl acetylenes catalyzed by silver salts

  摘要：

  Trimethylsilyl acetylenes can be selectively deprotected in the presence of a catalytic amount of silver salts. AgNO3 and AgOTf proved to be the most effective catalyst in a mixture of methanol, water and dichloromethane. Other functional groups, and especially silyl ethers, are not affected in these conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.017

文献信息

• Regio- and stereoselective synthesis of (Z)-β-silylalkenylboranes by silaboration of alkynes catalyzed by palladium and platinum complexes
  作者：Michinori Suginome、Takanori Matsuda、Hiroshi Nakamura、Yoshihiko Ito

  DOI：10.1016/s0040-4020(99)00444-5

  日期：1999.7

  Addition of the silicon-boron bonds of (dimethylphenylsilyl)boranes having pinacol, catechol, and diethylamino groups on the boron across carbon-carbon triple bonds is effectively catalyzed by palladium complexes. The silaboration of a variety of terminal alkynes took place with almost complete regio- and stereoselectivity to afford (Z)-1-boryl-2-silylalkenes in high yields. The silaboration products

  钯配合物可有效地催化硼上具有频哪醇，邻苯二酚和二乙氨基的（二甲基苯基甲硅烷基）硼烷的硅-硼键跨碳-碳三键的加成。各种末端炔的硅烷化反应几乎完全实现了区域和立体选择性，从而以高收率提供了（Z）-1-硼基-2-甲硅烷基烯烃。将硅烷化产物与芳基碘化物和铑催化的共轭物加到甲基乙烯基酮中进行钯催化的交叉偶联反应，分别以高收率得到β-甲硅烷基苯乙烯衍生物和δ-甲硅烷基-γ，δ-不饱和酮。 。
• Regio- and stereo-selective silaboration of alkynes catalysed by palladium and platinum complexes
  作者：Michinori Suginome、Hiroshi Nakamura、Yoshihiko Ito

  DOI：10.1039/cc9960002777

  日期：——

  Addition of the silicon–boron bond across carbon–carbon triple bonds, i.e. silaboration is most effectively catalysed by a palladium(0)–tert-alkyl isocyanide complex to give (Z)-1-boryl-2-silyl alkenes with high regio- and stereo-selectivity, which are useful for synthesis of stereodefined alkenylsilanes.

  硅-硼键通过碳-碳三键的添加，即硅硼化，最有效地由钯(0)-叔烷基异氰酸酯复合物催化，生成具有高区域选择性和立体选择性的(Z)-1-硼基-2-硅基烯烃，这些化合物对合成立体定义的烯丙基硅烷非常有用。
• Synthons for general routes to natural insecticidal lipid isobutylamides
  作者：Leslie Crombie、David Fisher

  DOI：10.1016/s0040-4039(00)94858-5

  日期：1985.1

  Four routes to the general amide synthon (4) are described. Synthons (33,R=H) and (36), suitable for a similar approach to other groups of natural isobutylamides, are also prepared.

  描述了通向一般酰胺合成子（4）的四种途径。还制备了适用于与天然异丁酰胺的其他基团相似的方法的合成子（33，R ＝ H）和（36）。
• Efficient Entry to the Pyrroloquinoline Core of<i>Martinella</i>Alkaloids via Novel Base-catalyzed Mukaiyama–Mannich Reaction
  作者：Shuhei Ikeda、Masatoshi Shibuya、Naoki Kanoh、Yoshiharu Iwabuchi

  DOI：10.1246/cl.2008.962

  日期：2008.9.5

  An efficient enantiocontrolled entry to Martinella alkaloids was achieved based on the unexpected discovery that a catalytic amount of KH/dicyclohexyl-18-crown-6 induced an intramolecular Mukaiyama-Mannich reaction of imine 3, leading to a cascade sequence involving a novel silyl group migration to furnish the pyrroloquinoline core 6.

  基于意外发现，催化量的 KH/dicyclohexyl-18-crown-6 诱导亚胺 3 的分子内 Mukaiyama-Mannich 反应，导致涉及新的甲硅烷基迁移的级联序列，实现了对 Martinella 生物碱的有效对映控制提供吡咯并喹啉核心 6.
• A chemoselective deprotection of trimethylsilyl acetylenes catalyzed by silver salts
  作者：Alban Orsini、Aurélien Vitérisi、Anne Bodlenner、Jean-Marc Weibel、Patrick Pale

  DOI：10.1016/j.tetlet.2005.02.017

  日期：2005.3

  Trimethylsilyl acetylenes can be selectively deprotected in the presence of a catalytic amount of silver salts. AgNO3 and AgOTf proved to be the most effective catalyst in a mixture of methanol, water and dichloromethane. Other functional groups, and especially silyl ethers, are not affected in these conditions. (c) 2005 Elsevier Ltd. All rights reserved.