(E)-oct-2-enoic acid chloride | 100808-08-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (E)-oct-2-enoic acid chloride
• 英文别名: 2-trans-octenoyl chloride；trans-2-octenoyl chloride；(E)-hex-3-enoyl chloride；(E)-oct-2-enoyl chloride；(E)-2-octenoyl chloride；trans-2-octenoic acid-chloride
• CAS: 100808-08-0
• 化学式: C₈H₁₃ClO
• 分子量: 160.644
• InChiKey: SUHXRRRGYUULBU-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-oct-2-enoic acid chloride 在 lithium aluminium tetrahydride 、 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 3.5h， 生成 (E)-1-bromo-oct-2-ene
  参考文献：
  名称：

  Binns, Malcolm R.; Haynes, Richard K.; Lambert, Dale E., Australian Journal of Chemistry, 1987, vol. 40, # 2, p. 281 - 290

  摘要：

  DOI：
• 作为产物：
  描述：

  正己醛 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (E)-oct-2-enoic acid chloride
  参考文献：
  名称：

  2,6-二取代萘萘的合成与氟硅酮林

  摘要：

  2,6-二取代萘衍生物的合成及液晶性能

  DOI：

  10.1002/hlca.19850680533

文献信息

• Visible light photocatalytic asymmetric synthesis of pyrrolo[1,2-<i>a</i>]indoles <i>via</i> intermolecular [3+2] cycloaddition
  作者：Antonio Casado-Sánchez、Pablo Domingo-Legarda、Silvia Cabrera、José Alemán

  DOI：10.1039/c9cc05838a

  日期：——

  The intermolecular diastereoselective and enantioselective synthesis of pyrrolo[1,2-a]indoles is developed through a [3+2] cycloaddition between silyl-indole derivatives and α,β-unsaturated N-acyl oxazolidinones by merging photocatalysis and Lewis acid catalysis.

  吡咯并[1,2- a ]吲哚的分子间非对映选择性和对映选择性合成是通过甲硅烷基吲哚衍生物与α，β-不饱和N-酰基恶唑烷酮通过光催化和路易斯酸催化的[3 + 2]环加成反应而开发的。
• Nucleophilic halo-Michael addition under Lewis-base activation
  作者：Víctor Laina-Martín、Ignacio Pérez、Jose A. Fernández-Salas、José Alemán

  DOI：10.1039/c9cc07068k

  日期：——

  A simple and general conjugate nucleophilic halogenation is presented. The THTO/halosilane combination has shown the ability to act as a nucleophilic halide source in the conjugate addition to a variety of Michael acceptors. In addition, a straightforward diastereoselective halogen installation using α,β-unsaturated acyloxazolidinones as platforms has been developed.

  提出了一种简单且通用的共轭亲核卤代。THTO /卤硅烷组合物已显示出在多种迈克尔受体的共轭物加成物中充当亲核卤化物源的能力。另外，已经开发了使用α，β-不饱和酰基恶唑烷二酮作为平台的简单的非对映选择性卤素装置。
• Inhibitory effect of 2-(E-2-alkenoylamino)ethyl alkyl sulfides on gastric ulceration in rats. I. Effect of 2-(E-2-alkenoylamino)ethyl carbamoylmethyl sulfides on gastric secretion and various ulceration models in rats.
  作者：MASAKAZU IWAI、ISAO KOHDA、CHIKARA FUKAYA、YOICHIRO NAITO、KAZUMASA YOKOYAMA、HIROSHI NAKAJIMA、KAZUTAKE TSUJIKAWA、MASARU OKABE、TSUTOMU MIMURA

  DOI：10.1248/cpb.35.4616

  日期：——

  Bis [2- (E-2-alkenoylaminoethyl)] disulfides (I) and 2- (E-2-alkenoylamino) ethyl carbamoylmethyl sulfides (II) with various alkenyl chain lengths were synthesized and their inhibitory effects on gastric secretion in rats were compared. There was a relationship between the alkenyl chain length of a series of sulfide derivatives (II) and their biological activities (C10 and C11 alkenyl derivatives were the most effective compounds). On the other hand, variation of the alkenyl chain length did not affect the anti-ulcerogenic activity of the disulfide derivatives (I). The derivatives (II) showed stronger biological activity than (I) when the same alkenyl group was present in both. The administration of 2- (E-2-decenoylamino) ethyl carbamoylmethyl sulfide (II-5) or 2- (E-2-undecenoylamino) ethyl carbamoylmethyl sulfide (II-6) at a dose of 20 mg/kg (i.p.) caused significant inhibition of various experimental ulcerations caused by stress, aspirin and HCl-ethanol. Oral administration of both acetamides (II-5, II-6) also caused 50-60% inhibition of ulceration in the water-immersion stress model at a dose of 20 mg/kg, although the activity was not as strong as that after i.p. injection. An improvement in anti-ulcerogenic activity was observed when acetamides were administered as a suspension in 10% HCO-60. Both acetamides (II-5, II-6) caused a dose-dependent decrease of the ulcer index of restrained and water-immersion stress-loaded rats in the dosage range from 0.5 mg/kg p.o. to 5 mg/kg p.o. The lethal dose 50% values (LD50) for both acetamides were over 8 g/kg (p.o. or i.p.).

  合成了各种烯烃链长度的双[2-(E-2-烯酰氨基乙基)]二硫化物 (I) 和 2-(E-2-烯酰氨基)乙基氨基甲基硫化物 (II)，并比较了它们对大鼠胃分泌的抑制作用。硫化物衍生物 (II) 的生物活性与烯烃链的长度之间存在一定关系（C10 和 C11 烯烃衍生物是最有效的化合物）。另一方面，烯烃链长度的变化并未影响二硫化物衍生物 (I) 的抗溃疡活性。当两者具有相同的烯烃基时，衍生物 (II) 的生物活性比 (I) 更强。以 20 mg/kg（i.p.）的剂量给药 2-(E-2-癸烯酰氨基)乙基氨基甲基硫化物 (II-5) 或 2-(E-2-十一烯酰氨基)乙基氨基甲基硫化物 (II-6) 显著抑制了由压力、阿司匹林和盐酸-乙醇引起的各种实验性溃疡。以 20 mg/kg 的剂量口服两种醋酸胺 (II-5, II-6) 也在水浸应激模型中引起了 50-60% 的溃疡抑制，尽管其活性不及腹腔注射后的强。以 10% HCO-60 悬浮液给药时，观察到醋酸胺的抗溃疡活性有所改善。这两种醋酸胺 (II-5, II-6) 在 0.5 mg/kg p.o. 到 5 mg/kg p.o. 剂量范围内引起了被限制和水浸应激负荷大鼠的溃疡指数的剂量依赖性下降。这两种醋酸胺的半数致死剂量 (LD50) 均超过 8 g/kg（口服或腹腔注射）。
• 2<i>H</i>-Pyran-2-ones from<i>Trichoderma viride</i>and<i>Trichoderma asperellum</i>
  作者：Susanne M. Wickel、Christian A. Citron、Jeroen S. Dickschat

  DOI：10.1002/ejoc.201300049

  日期：2013.5

  Volatiles emitted by the soil fungi Trichoderma viride 272 and Trichoderma asperellum 328 were collected by using the closed loop stripping analysis (CLSA) headspace technique, and the obtained extracts were analysed by GC/MS. Several alkyl- and alkenyl-2H-pyran-2-ones, including known compounds 6-pentyl-2H-pyran-2-one and (E)-6-(pent-1-en-1-yl)-2H-pyran-2-one, and the new derivatives (E)-6-(pent-

  土壤真菌绿色木霉 272 和木霉 328 释放的挥发物通过使用闭环汽提分析 (CLSA) 顶空技术收集，并通过 GC/MS 分析获得的提取物。几种烷基-和链烯基-2H-吡喃-2-酮，包括已知化合物 6-pentyl-2H-pyran-2-one 和 (E)-6-(pent-1-en-1-yl)-2H-pyran -2-one，以及新的衍生物 (E)-6-(pent-2-en-1-yl)-2H-pyran-2-one、6-丙基-2H-pyran-2-one 和 6-发现了庚基-2H-吡喃-2-one。还检测到烯基衍生物 (E)-6-(hept-1-en-1-yl)-2H-pyran-2-one，之前通过 MS 分析从海洋贵腐菌中初步鉴定出来。所有链烯基吡喃酮均通过使用报道的 Stille 偶联合成，然后进行内酯化，而烷基化吡喃酮是通过报道的合成方法通过 5-烷基戊-2-烯-5-内酯的自由基溴
• Synthesis of β,γ-unsaturated primary amides from α,β-unsaturated acids and investigation of the mechanism
  作者：Vassiliki Theodorou、Marina Gogou、Maria Philippidou、Valentine Ragoussis、Georgios Paraskevopoulos、Konstantinos Skobridis

  DOI：10.1016/j.tet.2011.05.096

  日期：2011.8

  α,β-Unsaturated acids, through their acid chlorides, react with tritylamine in the presence of triethylamine under mild conditions, to afford in high yield and high regioselectivity the corresponding β,γ-unsaturated tritylamides. Detritylation with TFA generates quantitatively β,γ-unsaturated primary amides. An investigation of this deconjugative isomerization was performed.

  α，β-不饱和酸，通过其酰氯，在温和的条件下，在三乙胺存在下与三苯甲基胺反应，以高收率和高区域选择性提供相应的β，γ-不饱和三苯乙酰胺。用TFA进行去三苯甲基化可定量生成β，γ-不饱和伯酰胺。对该解共轭异构化进行了研究。