1-吗啉-1-环庚烯 | 7182-08-3

• 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: 1-吗啉-1-环庚烯
• 英文名称: 4-(1-cyclohepten-1-yl)morpholine
• 英文别名: 4-(cyclohept-1-en-1-yl)morpholine；1-Morpholinocycloheptene；1-morpholino-1-cycloheptene；4-(cyclohepten-1-yl)morpholine
• CAS: 7182-08-3
• 化学式: C₁₁H₁₉NO
• mdl: MFCD00192335
• 分子量: 181.278
• InChiKey: HLVQJUUPEMTTIS-UHFFFAOYSA-N

物化性质

• 沸点：
  108 °C/4 mmHg(lit.)
• 密度：
  0.994 g/mL at 25 °C(lit.)
• 闪点：
  94 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.818
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38

反应信息

• 作为反应物：
  描述：

  1-吗啉-1-环庚烯 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 生成 (+/-)-2-oxo-cis-decahydro-1H-benzocycloheptene
  参考文献：
  名称：

  Transannular reactions of cycloalkenes, cycloalkadienes and cycloalkatrienes. 16. Photocyclization of cyclononene and cycloundecene

  摘要：

  Irradiation of cyclononene (7b) and cycloundecene (7d) in pentane afforded cis-bicyclo[4.3.0]nonane (10b) and cis-bicyclo[6.3.0]undecane (10d), respectively. Small amounts of the fragmentation products 1-undecene (14d) and 1-undecyne (15d) were also obtained from cycloundecene (7d). The photobehavior of the series of medium- and large-ring alkenes 7a-e is compared. Aside from E reversible Z isomerization, the principal pathway in each case involves rearrangement of the pi,R(3s) excited state to the cycloalkylidene intermediate 8, which undergoes predominant, if not exclusive, 1,5-transannular insertion to afford the corresponding cis-bicyclo[n.3.0]alkane (10). The cycloalkylidenes 8 formed in this way exhibit behavior somewhat different from those generated by other methods. The possible contributory role of carbene intermediates derived from pi,R(3s) excited states in E revesible Z photoisomerization of acyclic alkenes is also discussed.

  DOI：

  10.1021/jo00013a041
• 作为产物：
  描述：

  吗啉 、 环庚酮 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 1-吗啉-1-环庚烯
  参考文献：
  名称：

  Discovery of quinolone derivatives as antimycobacterial agents

  摘要：

  6b21：对H37Rv结核分枝杆菌的最小抑菌浓度为1.2 μg/mL，对耐药菌株的最小抑菌浓度为0.9 μg/mL，溶解度为132 μg/mL，无细胞毒性。

  DOI：

  10.1039/d0ra09250a

文献信息

• Hexahydro-cyclohepta-pyrrole oxindole as potent kinase inhibitors
  申请人：SUGEN, Inc.

  公开号：US20040186160A1

  公开（公告）日：2004-09-23

  The present invention is directed to a class indolinone compounds, hexahydro-cyclohepta-pyrrole oxindoles, which are useful as protein kinase inhibitors.

  本发明涉及一类吲哚酮化合物，即六氢-环庚-吡咯酮氧吲哚，其作为蛋白激酶抑制剂具有用途。
• Cyclic Seleninate Esters as Catalysts for the Oxidation of Sulfides to Sulfoxides, Epoxidation of Alkenes, and Conversion of Enamines to α-Hydroxyketones
  作者：Eric A. Mercier、Chris D. Smith、Masood Parvez、Thomas G. Back

  DOI：10.1021/jo300313v

  日期：2012.4.6

  sulfides to sulfoxides, alkenes to epoxides, and enamines to α-hydroxyketones. Optimal conditions were found that minimize the overoxidation of the product sulfoxides to sulfones and the hydrolysis of epoxides to diols. In some examples such as styrene derivatives, oxidative cleavage was observed instead of epoxidation. The enamine oxidations proceed via the initial formation of dimeric 2,5-diamino-1

  环状硒代酸酯用作将硫化物快速氧化为亚砜，将烯烃快速氧化为环氧化物以及将烯胺快速氧化为α-羟基酮的催化剂。发现最佳条件使产物亚砜至砜的过氧化和环氧化物至二醇的水解减至最小。在某些实例中，例如苯乙烯衍生物，观察到氧化裂解而不是环氧化。烯胺的氧化过程是通过最初形成二聚2,5-二氨基-1,4-二恶烷物质而进行的，将其原位水解为最终产物。一种这样的二聚体的结构通过X射线晶体学确认。
• Functionalized chloroenamines in aminocyclopropane synthesis I. — bicyclic and pentacyclic lactams from carbamoylated chloroenamines
  作者：Peter Altmeier、Elmar Vilsmaier、Gotthelf Wolmershäuser

  DOI：10.1016/s0040-4020(01)80145-9

  日期：1989.1

  enamine 11c a bicyclic β-lactam 16c was isolated as primary product, which rearranged to the conjugated chloroenamine 15c via its non-conjugated isomer 14c. In acetonitrile as a solvent this isomerization additionally produced a methylene pyrroline derivative 19c as byproduct. Interaction of 15a-d with succinimide (20) gave succinimido cis-bicycloalkane carboxamides 21a-d. A trans bicyclic carboxamide

  通过将环烯胺11与芳基异氰酸酯酰化并随后使用NCS进行氯化，来合成氨基甲酰化的氯烯胺15。在七元烯胺11c的情况下，分离出双环β-内酰胺16c作为初级产物，其通过其非共轭异构体14c重排至共轭二氯胺15c。在作为溶剂的乙腈中，该异构化另外产生了作为副产物的亚甲基吡咯啉衍生物19c。15a-d与琥珀酰亚胺（20）的相互作用产生了琥珀酰亚胺基顺式-双环烷烃羧酰胺21a-d。反式双环羧酰胺22e是通过X射线结构分析确定的15e的类似反应产生的。在加热21或22时，在高烯胺型反应中产生双环内酰胺25。氢化锂铝将25a还原生成二胺26。相应的25c反应，e生成吡咯衍生物27c，e。通过在乙腈中加热15b，d而不添加亲核试剂来形成五环内酰胺28b，d。还原28d得到五环二胺29d。
• Generation and trapping of electron-deficient 1,2-cyclohexadienes. Unexpected hetero-Diels–Alder reactivity
  作者：Baolei Wang、Marius-Georgian Constantin、Simarpreet Singh、Yuqiao Zhou、Rebecca L. Davis、F. G. West

  DOI：10.1039/d0ob02285c

  日期：——

  base-mediated (KOt-Bu) elimination, and found to dimerize via an unprecedented formal hetero-Diels–Alder process, followed by hydration. These highly reactive cyclic allene intermediates were also trapped in Diels–Alder reactions by furan, 2,5-dimethylfuran, or diphenylisobenzofuran to afford cycloadducts with high regio- and diastereoselectivity, and could also be intercepted in a hetero-Diels–Alder

  酮基取代的1，2-环己二烯是通过碱基介导的（KO t -Bu）消除而生成的，并发现通过史无前例的正式异Diels-Alder过程二聚，然后水合。这些高反应性的环状丙二烯中间体也通过呋喃，2,5-二甲基呋喃或二苯基异苯并呋喃被困在Diels-Alder反应中，以提供具有高区域和非对映选择性的环加合物，也可能在烯胺的异Diels-Alder工艺中被拦截双亲物。内切/外切立体化学明确地通过腈取代的1,2-环己二烯的X射线晶体学分析。DFT计算表明，用这些异位烯观察到的新型杂-Diels-Alder过程是通过协同的异步环加成机理发生的。
• Photochemical ring-contraction of fused bicyclic 4-pyrones: A novel 2-step cyclopentannulation approach
  作者：F.G. West、P.V. Fisher、G.U. Gunawardena、Scott Mitchell

  DOI：10.1016/s0040-4039(00)60630-5

  日期：1993.9

  Fused bicyclic 4-pyrones were prepared by condensation of enamines derived from cyclic ketones with diketene or substituted 1,3-dioxin-4-ones. Photolysis in a hydroxylic medium led to bicyclo[n3.0]alkenones bearing oxygenation at both angular positions. This process is occurs via regioselective nucleophilic solvent attack on the intermediate tricyclic oxyallyl zwitterion. The efficiency of the transformation

  稠合的双环4-吡喃酮是通过将环酮衍生的烯胺与双烯酮或取代的1,3-二恶英-4-酮缩合而制备的。在羟基介质中的光解导致双环[n3.0]烯酮在两个角位置均带有氧合。该过程是通过区域选择性亲核溶剂攻击中间的三环氧基烯丙基两性离子而发生的。发现转化效率取决于与4-吡喃酮稠合的环的大小。

表征谱图