2-甲基-1-吗啉代-1-戊烯 | 147050-27-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 中文名称: 2-甲基-1-吗啉代-1-戊烯
• 英文名称: 2-Methyl-1-morpholino-1-pentene
• 英文别名: 4-(2-methylpent-1-enyl)morpholine
• CAS: 147050-27-9
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: IZNQYLVTGFEQIT-UHFFFAOYSA-N

物化性质

• 沸点：
  253.9±29.0 °C(Predicted)
• 密度：
  0.974±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基-1-吗啉代-1-戊烯 在 di(rhodium)tetracarbonyl dichloride 水 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 70.0~140.0 ℃ 、5.07 MPa 条件下， 反应 96.0h， 生成 1-(Diethyl-methyl-silanyloxy)-3-methyl-hexan-2-one
  参考文献：
  名称：

  Regioselective incorporation of CO into enamines by rhodium-catalyzed reaction with a hydrosilane and CO

  摘要：

  In the presence of [RhCl(CO)2]2, the reaction of enamines with a hydrosilane and carbon monoxide (140-degrees-C, 50 atm of CO) resulted in regioselective incorporation of CO into the alpha-carbon atom to give alpha-(siloxymethylene) amines, which can be easily converted into alpha-siloxy ketones by hydrolysis.

  DOI：

  10.1021/jo00027a002
• 作为产物：
  描述：

  吗啉 、 2-甲基戊醛 生成 2-甲基-1-吗啉代-1-戊烯
  参考文献：
  名称：

  Regioselective incorporation of CO into enamines by rhodium-catalyzed reaction with a hydrosilane and CO

  摘要：

  In the presence of [RhCl(CO)2]2, the reaction of enamines with a hydrosilane and carbon monoxide (140-degrees-C, 50 atm of CO) resulted in regioselective incorporation of CO into the alpha-carbon atom to give alpha-(siloxymethylene) amines, which can be easily converted into alpha-siloxy ketones by hydrolysis.

  DOI：

  10.1021/jo00027a002

文献信息

• Enamine oxidations. 2. Selective oxidative cleavage of β,β - disubstituted enamines using alumina supported permanganate. Synthesis of one-carbon dehomologated carbonyl compounds from enamines
  作者：Clifford E. Harris、William Chrisman、Sally A. Bickford、Lawrence Y. Lee、Antonia E. Torreblanca、Bakthan Singaram

  DOI：10.1016/s0040-4039(96)02504-x

  日期：1997.2

  selective oxidative cleavage reaction which produces ketones and formamides. The ketones can be isolated in high yield and purity by a simple workup procedure. The oxidizing agent is selective and preferentially oxidizes an enamine carbon-carbon double bond in the presence of a distal carbon-carbon double bond. Other functional groups unaffected by this reagent include nitriles, secondary alcohols, and

  用中性氧化铝上负载的高锰酸钾处理β，β-二取代的烯胺会产生温和的选择性氧化裂解反应，产生酮和甲酰胺。可以通过简单的后处理程序以高收率和高纯度分离出酮。氧化剂是选择性的，并且在远端碳-碳双键的存在下优先氧化烯胺碳-碳双键。不受该试剂影响的其他官能团包括腈，仲醇和炔烃，可实现多种潜在的选择性氧化。
• Zeolite supported permanganate: An efficient catalyst for selective oxidation of enamines, alkylarenes and unsaturated alcohols
  作者：R. Sreekumar、Raghavakaimal Padmakumar

  DOI：10.1016/s0040-4039(97)01096-4

  日期：1997.7

  supported on zeolite can be used for the selective oxidation of various enamines, alkylarenes and unsaturated alcohols to the corresponding ketones, in good yield. Arenes were selectively oxidized at the benzylic position. If the benzylic carbon is secondary, ketones are obtained, and alcohols are produced if the benzylic position is tertiary. In contrast unsaturated secondary alcohols selectively undergo

  负载在沸石上的高锰酸钾可用于以高收率将各种烯胺，烷基芳烃和不饱和醇选择性氧化为相应的酮。芳烃在苄基位置被选择性地氧化。如果苄基碳是仲的，则得到酮，并且如果苄基的位置是叔的，则产生醇。相反，不饱和仲醇选择性地氧化成相应的烯酮而不影响碳-碳双键。
• Fisher, Gary B.; Juarez-Brambila, Jesus J.; Gorakki, Christian T., Journal of the American Chemical Society, 1993, vol. 115, # 2, p. 440 - 444
  作者：Fisher, Gary B.、Juarez-Brambila, Jesus J.、Gorakki, Christian T.、Wipke, W. Todd、Singaram, Bakthan

  DOI：——

  日期：——
• Unusual directive effects in the hydroboration of .beta.,.beta.-disubstituted enamines. Conversion of .alpha.-substituted aldehydes to the corresponding alkenes and .beta.-amino alcohols
  作者：Bakthan Singaram、Christian T. Goralski、Gary B. Fisher

  DOI：10.1021/jo00019a043

  日期：1991.9

  A comprehensive study of the conversion of beta,beta-disubstituted enamines into the corresponding alkenes and beta-amino alcohols by hydroboration-elimination and hydroboration-oxidation, respectively, has been carried out. The amine moiety of beta,beta-disubstituted enamines was found to exert a decisive influence on the regioselectivity of the hydroboration reaction involving borane methyl sulfide (BMS). Thus, in the hydroboration of morpholino and piperidino enamines, the boron atom is initially placed predominantly in the alpha-position. Conversely, the pyrrolidino enamines direct the boron atom exclusively to the beta-position. Three oxidizing agents, trimethylamine N-oxide, sodium perborate, and 30% hydrogen peroxide-solid sodium hydroxide, were tried in order to optimize the oxidation of the intermediate organoborane derivatives to the corresponding amino alcohols. Our results clearly indicated that 30% hydrogen peroxide-solid sodium hydroxide is best suited for this transformation. The yield of amino alcohol ranged from good to essentially quantitative. Enamines derived from beta-aryl aldehydes, upon hydroboration with BMS followed by methanolysis and oxidation with neutral hydrogen peroxide, gave the corresponding 1,1-disubstituted alkenes. Contrary to the regioselectivity observed in the hydroboration reactions involving BMS, the hydroboration of beta,beta-disubstituted enamines using 9-borabicyclo[3.3.1]nonane (9-BBN) gave the trialkylborane intermediates in which the boron atom was placed exclusively at the beta-position regardless of the amine moiety of the enamine. These trialkylborane derivatives were very stable and did not undergo the usual elimination reaction with either methanol or sodium hydroxide. However, on thermal decomposition, these afforded the corresponding 1,1-disubstituted alkenes in high yields.