carbomethoxyhydrazone of 3-pentanone | 68180-96-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: carbomethoxyhydrazone of 3-pentanone
• 英文别名: 3-Pentanone carbomethoxyhydrazone；(1-ethyl-propylidene)-carbazic acid methyl ester；(1-Aethyl-propyliden)-carbazidsaeure-methylester；Pentan-3-on-(methoxycarbonyl-hydrazon)；Methyl 2-(pentan-3-ylidene)hydrazine-1-carboxylate；methyl N-(pentan-3-ylideneamino)carbamate
• CAS: 68180-96-1
• 化学式: C₇H₁₄N₂O₂
• 分子量: 158.2
• InChiKey: JUDUYWGEMZJPGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  carbomethoxyhydrazone of 3-pentanone 在 氰化钠 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 4.7h， 生成 2-乙基丁腈
  参考文献：
  名称：

  Electrochemical oxidation of ketone acylhydrazones and their hydrogen cyanide adducts in sodium cyanide-methanol. Transformation of ketones to nitriles

  摘要：

  DOI：

  10.1021/jo00290a048
• 作为产物：
  描述：

  肼基甲酸甲酯 、 3-戊酮 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 carbomethoxyhydrazone of 3-pentanone
  参考文献：
  名称：

  Electrochemical oxidation of ketone acylhydrazones and their hydrogen cyanide adducts in sodium cyanide-methanol. Transformation of ketones to nitriles

  摘要：

  DOI：

  10.1021/jo00290a048

文献信息

• Carbazic Acid Esters as Carbonyl Reagents
  作者：Norman Rabjohn、H. D. Barnstorff

  DOI：10.1021/ja01105a513

  日期：1953.5
• Electrochemical oxidation of ketone acylhydrazones and their hydrogen cyanide adducts in sodium cyanide-methanol. Transformation of ketones to nitriles
  作者：Mitsuhiro Okimoto、Toshiro Chiba

  DOI：10.1021/jo00290a048

  日期：1990.2
• Rate Constants for 1,2-Hydrogen Migration in Cyclohexylidene and in Substituted Cyclohexylidenes¹
  作者：John Paul Pezacki、Philippe Couture、James A. Dunn、John Warkentin、Paul D. Wood、Janusz Lusztyk、Francis Ford、Matthew S. Platz

  DOI：10.1021/jo990171q

  日期：1999.6.1

  Laser Bash photolysis (UV-LFP, 308 nm) of suitably substituted oxadiazolines leads to cyclohexylidene (14a), 4-tert-butyl-cyclohexylidene (14b), 2-trifluoromethylcyclohexylidene (14d), 8-aza-8methyl[3.2.1]oct-3-ylidene (14e), diethylcarbene (14f), and ethyl(methyl)carbene (14h). Carbene intermediates were inferred from the products of steady state photolyses, and their pyridinium ylides were inferred from. transient absorption spectra observed when pyridine was present. Yields of the pyridinium ylides 15a-h as a function of pyridine concentration gave the lifetimes (tau) for carbenes 14a-h in cyclohexane, cyclohexane-d(12), and benzene solutions, at 22 degrees C. The intermediacy of cyclohexylidene (14a) was inferred from the observation of cyclohexene formed in both the LFP and steady state (SS) experiments, The major products from dual wavelength irradiation of the oxadiazolines (at 254 and 300 nm) were those of 1,2-migration of hydrogen (1,2-H) in the corresponding carbenes. 2-Trifluromethylcyclohexylidene gave 3-trifluoromethylcyclohexene and 1-trifluoromethylcyclohexene in a 9.8:1 ratio. The kinetic data support the conclusion that 1,2-H in the cyclohexylidenes is accelerated, relative to 1,2-H in dimethylcarbene. A 4-tert-butyl substituent has a negligible effect on the rate constant for 1,2-H, but the CF3 group at the alpha-position decelerates 1,2-H by roughly: 10-fold, as inferred from the distribution of products.