-1-Morpholino-1-octene | 96517-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: -1-Morpholino-1-octene
• 英文别名: (E)-1-(4-Morpholino)-1-octene；(E)-1-morpholino-1-octene；4-[(E)-oct-1-enyl]morpholine
• CAS: 96517-27-0
• 化学式: C₁₂H₂₃NO
• 分子量: 197.321
• InChiKey: DMWHBJKPNPVVMN-BQYQJAHWSA-N

物化性质

• 沸点：
  289.2±29.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  -1-Morpholino-1-octene 在 甲醇 、 9-borabicyclo[3.3.1]nonane dimer 作用下， 生成 辛烯
  参考文献：
  名称：

  Hydroboration. 86. Convenient conversion of aldehydes and ketones into the corresponding alkenes via hydroboration of their enamines. A remarkably simple synthesis of either (Z)- or (E)-alkenes

  摘要：

  Aldehydes and ketones are converted into the corresponding alkenes via hydroboration of their enamines. Hydroboration of aldehyde enamines by 9-borabicyclo[3.3.1]nonane (9-BBN), followed by methanolysis, affords the corresponding terminal alkenes in 75-90% yields. Unsaturated aldehyde enamines produce the corresponding dienes under these conditions. Enamines derived from substituted cyclic ketones and heterocyclic ketones are readily accommodated in this reaction to afford the corresponding alkenes in very good yields. The synthesis of pure (Z)- or (E)-alkenes is readily achieved from the same acyclic ketone enamine by modification of the hydroboration-elimination procedure: (A) hydroboration by 9-BBN followed by methanolysis or (B) hydroboration by borane methyl sulfide (BMS) followed by methanolysis and hydrogen peroxide oxidation. Mechanistic rationale is provided.

  DOI：

  10.1021/jo00004a038
• 作为产物：
  描述：

  吗啉 在 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 -1-Morpholino-1-octene
  参考文献：
  名称：

  Stereospecific synthesis of enamines from α,β-epoxysilanes

  摘要：

  DOI：

  10.1016/s0040-4039(00)61863-4

文献信息

• Anti-Markovnikov Addition of Both Primary and Secondary Amines to Terminal Alkynes Catalyzed by the TpRh(C₂H₄)₂/PPh₃ System
  作者：Yoshiya Fukumoto、Harumi Asai、Masaki Shimizu、Naoto Chatani

  DOI：10.1021/ja075484e

  日期：2007.11.1

  Terminal alkynes react with secondary amines in the presence of TpRh(C2H4)2/PPh3 (Tp = trispyrazolylborate) to give anti-Markovnikov E-enamines. Both Tp and PPh3 ligands are essential for the reaction. The reaction tolerates functional groups, such as ester, nitrile, and siloxy groups, on the terminal alkynes. Primary amines also add to terminal alkynes in anti-Markovnikov fashion, yielding the corresponding

  末端炔烃在 TpRh(C2H4)2/PPh3（Tp = 三吡唑基硼酸酯）存在下与仲胺反应，得到抗马尔科夫尼科夫 E-烯胺。Tp 和 PPh3 配体对于反应都是必不可少的。该反应耐受末端炔烃上的官能团，例如酯、腈和甲硅烷氧基。伯胺也以反马尔科夫尼科夫方式加到末端炔烃上，产生相应的亚胺。亚乙烯基-铑配合物的形成，然后是亚乙烯基-金属中间体的α-碳原子上的胺氮分子间亲核攻击，这可能是催化反应的关键步骤。
• Boranes in Synthesis. 1. Asymmetric synthesis of β-amino alcohols. A facile conversion of enamines to the corresponding β-amino alcohols in high enantiomeric purity
  作者：Gary B. Fisher、Christian T. Goralski、Lawrence W. Nicholson、Bakthan Singaram

  DOI：10.1016/s0040-4039(00)61541-1

  日期：1993.11

  The asymmetric hydroboration of aldehyde enamines with dIpc2BH at 0 °C, followed by oxidation with NaOH(s)/H2O2, yields the corresponding β-amino alcohols in good yields and high enantiomeric excess.

  醛烯胺与d Ipc 2 BH在0°C下不对称氢硼化，然后用NaOH / H 2 O 2氧化，得到相应的β-氨基醇，收率高，对映体过量高。
• Convenient conversion of aldehydes and ketones into the corresponding alkenes via hydroboration of their enamines. A remarkably simple synthesis of either (Z)- or (E)-alkenes
  作者：Bakthan Singaram、Christian T. Goralski、Milind V. Rangaishenvi、Herbert C. Brown

  DOI：10.1021/ja00183a068

  日期：1989.1
• Sucrow, Wolfgang; Minas, Hermann; Stegemeyer, Horst, Chemische Berichte, 1985, vol. 118, # 8, p. 3332 - 3349
  作者：Sucrow, Wolfgang、Minas, Hermann、Stegemeyer, Horst、Geschwinder, Peter、Murawski, Hans-Ruediger、Krueger, Carl

  DOI：——

  日期：——
• A Facile New Synthesis of Aldehyde Enamines in High Yield and High Purity
  作者：Gary B. Fisher、Lawrence Lee、Frederick W. Klettke

  DOI：10.1080/00397919408010154

  日期：1994.6

  Aldehyde enamines were synthesized in excellent yield and purity by reacting an aldehyde with 2 equivalents of a secondary amine in cyclohexane in the presence of 1.5 equivalents of CaH2. Distilled yields ranged from 65%-92%.