(Z)-1-bromo-2-nonen-4-yne | 67978-52-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: (Z)-1-bromo-2-nonen-4-yne
• 英文别名: (Z)-1-bromonon-2-en-4-yne
• CAS: 67978-52-3
• 化学式: C₉H₁₃Br
• 分子量: 201.106
• InChiKey: HICZQAKERXXSNZ-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (Z)-1-bromo-2-nonen-4-yne 在 间氯过氧苯甲酸 作用下， 以 苯 为溶剂， 反应 26.0h， 生成 (2aRS,5aSR,8bRS)-8-butyl-1,2,2a,3,5,5a,7,8b-octahydro-4,6-dioxaacenaphthylene-1,7-dione
  参考文献：
  名称：

  A New Co₂(CO)₈-Mediated Tandem [5 + 1]/[2 + 2 + 1]-Cycloaddition Reaction:  A One-Pot Synthesis of Tricyclic δ-Lactones from cis-Epoxy Ene-ynes

  摘要：

  In the presence of Co2(CO)8 and CO, cis-epoxyalkynes bearing a tether olefin undergo a tandem [5 + 1]/[2 + 2 + 1]-cycloaddition to give tricyclic delta-lactones efficiently in a one-pot operation. The reaction mechanism is proposed to involve a cobalt-coordinated cyclic allene species.

  DOI：

  10.1021/ja0346633
• 作为产物：
  描述：

  methyl (Z)-non-2-en-4-ynoate 在 二异丁基氢化铝 、 三苯基膦 作用下， 生成 (Z)-1-bromo-2-nonen-4-yne
  参考文献：
  名称：

  A New Co₂(CO)₈-Mediated Tandem [5 + 1]/[2 + 2 + 1]-Cycloaddition Reaction:  A One-Pot Synthesis of Tricyclic δ-Lactones from cis-Epoxy Ene-ynes

  摘要：

  In the presence of Co2(CO)8 and CO, cis-epoxyalkynes bearing a tether olefin undergo a tandem [5 + 1]/[2 + 2 + 1]-cycloaddition to give tricyclic delta-lactones efficiently in a one-pot operation. The reaction mechanism is proposed to involve a cobalt-coordinated cyclic allene species.

  DOI：

  10.1021/ja0346633

文献信息

• Synthesis and antifungal activity of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethanamine (SF 86-327) and related allylamine derivatives with enhanced oral activity
  作者：Anton Stuetz、Gabor Petranyi

  DOI：10.1021/jm00378a003

  日期：1984.12

  The allylamine derivatives are a new class of synthetic antifungal agents inhibiting fungal squalene epoxidase. A new subclass, which features an acetylene group conjugated with the allylamine double bond, is characterized by enhanced antifungal activity, especially on oral treatment of guinea pig dermatophytoses. Increased branching of the alkyl group next to the triple bond led to the tert-butylacetylene

  烯丙胺衍生物是抑制真菌角鲨烯环氧酶的一类新的合成抗真菌剂。一个新的亚类，具有与烯丙基胺双键结合的乙炔基团，其特点是增强的抗真菌活性，特别是在豚鼠皮肤癣菌的口服治疗中。靠近三键的烷基支链的增加导致了叔丁基乙炔衍生物SF 86-327，该化合物在体内外的活性均显着提高，目前正在临床评估中。介绍了通用的合成路线，可比较的生物学数据以及构效关系。
• General and Regioselective Synthesis of Substituted Pyrroles by Metal-Catalyzed or Spontaneous Cycloisomerization of (<i>Z</i>)-(2-En-4-ynyl)amines
  作者：Bartolo Gabriele、Giuseppe Salerno、Alessia Fazio

  DOI：10.1021/jo034850j

  日期：2003.10.1

  A general and regioselective synthesis of substituted pyrroles 2 by cycloisomerization of readily available (Z)-(2-en-4-ynyl)amines 1 is reported. Spontaneous cycloisomerization leading to 2 occurred in the course of preparation of enynamines bearing a terminal triple bond or a triple bond substituted with a phenyl or a CH2OTHP group. When the triple bond was substituted with an alkyl or alkenyl group

  据报道，通过容易获得的（Z）-（2-en-4-炔基）胺1的环异构化，一般和区域选择性地合成取代的吡咯2。在制备带有末端三键或被苯基或CH 2 OTHP基团取代的三键的烯胺的过程中发生自发的环异构化反应，导致2。当三键被烷基或烯基取代时，烯胺是稳定的并且可以通过金属催化转化为相应的吡咯。发现CuCl2是用于在C-3处取代的底物进行环异构化的出色催化剂，而PdX2与KX（X = Cl，I）结合使用则是在C-3处未取代的烯胺反应的优良催化剂。
• A stereoselective synthesis of (E)-1-halo-6,6-dimethyl-2-hepten-4-yne: a key intermediate for terbinafine
  作者：Shan-Yen Chou、Chin-Lu Tseng、Shyh-Fong Chen

  DOI：10.1016/s0040-4039(00)00511-6

  日期：2000.5

  A study of the stereoselective halogenation of 6,6-dimethyl-1-hepten-4-yn-3-ol (1) using a series of halogenating agents is described. Of the many agents investigated, boron trichloride is the most successful reagent for stereoselective halogenation (E:Z=9:1max). The resulting (E)-1-halo-6,6-dimethyl-2-hepten-4-yne (2), a key intermediate for terbinafine, an antifungal agent, is obtained in good yield

  描述了使用一系列卤化剂对6,6-二甲基-1-庚烯-4-yn-3-ol（1）进行立体选择性卤化的研究。在研究的许多试剂中，三氯化硼是最成功的立体选择性卤化试剂（E：Z = 9：1 max）。以良好的收率和立体选择性获得了所得的（E）-1-卤代-6,6-二甲基-2-庚基-4-炔（2），这是特比萘芬（一种抗真菌剂）的关键中间体。同样研究了两种结构相关的炔烃，并显示了相似的通用性。
• Versatile Synthesis of Pyrrole-2-acetic Esters and (Pyridine-2-one)-3-acetic Amides by Palladium-Catalyzed, Carbon Dioxide-Promoted Oxidative Carbonylation of (Z)-(2-En-4-ynyl)amines
  作者：Bartolo Gabriele、Giuseppe Salerno、Alessia Fazio、Lucia Veltri

  DOI：10.1002/adsc.200606085

  日期：2006.10

  The oxidative carbonylation of readily available (Z)-(2-en-4-ynyl)amines, catalyzed by the PdI2-KI system, selectively afforded in satisfactory yields (40–95 %) either pyrrole-2-acetic ester or (pyridine-2-one)-3-acetic amide derivatives, depending on the susbtitution pattern of the substrate and the reaction conditions. The presence of an excess of carbon dioxide proved in most cases to be beneficial

  由PdI 2 -KI体系催化的，易于获得的（Z）-（2-en-4-ynyl）胺的氧化羰基化选择性地提供了令人满意的产率（40-95％）的吡咯-2-乙酸酯或（吡啶-2-酮）-3-乙酰胺衍生物，取决于底物的取代方式和反应条件。在大多数情况下，过量二氧化碳的存在对反应速率和产物选择性都有利。