1-环戊基-2-甲氧基乙酮 | 14966-80-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-环戊基-2-甲氧基乙酮
• 英文名称: 1-cyclopentyl-2-methoxyethanone
• 英文别名: 1-cyclopentyl-2-methoxy-ethanone；1-Cyclopentyl-2-methoxy-aethanon；1-Cyclopentyl-2-methoxyethan-1-one
• CAS: 14966-80-4
• 化学式: C₈H₁₄O₂
• mdl: MFCD11555828
• 分子量: 142.198
• InChiKey: PYPUDSQLJBSGCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  86-87 °C(Press: 14 Torr)
• 密度：
  0.995±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.875
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-环戊基-2-甲氧基乙酮 、 2,4-二硝基苯肼 在 硫酸 作用下， 以 乙醇 、 水 为溶剂， 以68 mg的产率得到1-(1-cyclopentyl-2-methoxyethylidene)-2-(2,4-dinitrophenyl)hydrazine
  参考文献：
  名称：

  Diisopropyloxy(η2-cyclopentene)titanium for the diastereoselective synthesis of various 1,2-disubstituted cyclopentanes

  摘要：

  The reaction of 3 equiv of cyclopentylmagnesium chloride with 2 equiv of titanium(IV) isopropoxide at low temperature (-70 to -50 degrees C) leads to the formation of 1 equiv of diisopropyloxy(eta(2)-cyclopentene)titanium containing low amounts of the starting Grignard reagent. The sequential addition of two electrophiles onto this titanium complex involved as an intermediate in Kulinkovich-type reactions delivers various 1,2-disubstituted cyclopentane rings with generally high diastereoselectivity. Mechanistic considerations and possible extensions of this method are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.08.117
• 作为产物：
  描述：

  甲氧基乙腈 、 Cyclopentylmagnesium chloride 在 乙醚 作用下， 生成 1-环戊基-2-甲氧基乙酮
  参考文献：
  名称：

  Ranganathan, Current Science, 1940, vol. 9, p. 458

  摘要：

  DOI：

文献信息

• A NEW SYNTHETIC METHOD FOR 1-METHOXY-2-ALKANONES FROM 1,2-DIMETHOXYETHENYLLITHIUM AND ORGANOBORANES
  作者：Junji Koshino、Takahiro Sugawara、Toshinobu Yogo、Akira Suzuki

  DOI：10.1246/cl.1983.933

  日期：1983.6.5

  1-Methoxy-2-alkanones are prepared from ate-complexes formed from 1,2-dimethoxyethenyllithium and trialkylboranes by the reaction with BF3:Et2O, followed by basic hydrogen peroxide oxidation.

  1-甲氧基-2-烷酮是通过以下方法制备的：由1,2-二甲氧基乙烯基锂与三烷基硼烷形成的络合物，经BF3:Et2O反应后，再用碱性过氧化氢进行氧化。
• Ranganathan, Current Science, 1940, vol. 9, p. 458
  作者：Ranganathan

  DOI：——

  日期：——
• KOSHINO, JUNJI;SUGAWARA, TAKAHIRO;YOGO, TOSHINOBU;SUZUKI, AKIRA, CHEM. LETT., 1983, N 6, 933-934
  作者：KOSHINO, JUNJI、SUGAWARA, TAKAHIRO、YOGO, TOSHINOBU、SUZUKI, AKIRA

  DOI：——

  日期：——
• STUDIES ON LACTONES RELATED TO THE CARDIAC AGLYCONES. I. SYNTHESIS OF β-SUBSTITUTED Δ^α,β-BUTENOLIDES FROM ι-METHOXYMETHYL KETONES
  作者：MARTIN RUBIN、WALTER D. PAIST、ROBERT C. ELDERFIELD

  DOI：10.1021/jo01202a010

  日期：1941.3
• Diisopropyloxy(η2-cyclopentene)titanium for the diastereoselective synthesis of various 1,2-disubstituted cyclopentanes
  作者：Frédéric Cadoret、Pascal Retailleau、Yvan Six

  DOI：10.1016/j.tetlet.2006.08.117

  日期：2006.10

  The reaction of 3 equiv of cyclopentylmagnesium chloride with 2 equiv of titanium(IV) isopropoxide at low temperature (-70 to -50 degrees C) leads to the formation of 1 equiv of diisopropyloxy(eta(2)-cyclopentene)titanium containing low amounts of the starting Grignard reagent. The sequential addition of two electrophiles onto this titanium complex involved as an intermediate in Kulinkovich-type reactions delivers various 1,2-disubstituted cyclopentane rings with generally high diastereoselectivity. Mechanistic considerations and possible extensions of this method are discussed. (c) 2006 Elsevier Ltd. All rights reserved.