1-cyano-5-heptyne | 124855-70-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-cyano-5-heptyne
• 英文别名: Oct-6-ynenitrile
• CAS: 124855-70-5
• 化学式: C₈H₁₁N
• 分子量: 121.182
• InChiKey: OBTJNKFYRNQIQG-UHFFFAOYSA-N

物化性质

• 沸点：
  88-95 °C(Press: 5 Torr)
• 密度：
  0.882±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-cyano-5-heptyne 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 oct-6-ynoic acid
  参考文献：
  名称：

  某些六元，七元和八元酸的分子内酰化作用

  摘要：

  在100°下用多磷酸处理七种异构体己烯酸中的任何一种，得到的环己-2-烯酮，2-甲基环戊-2-烯酮和己烯-4-和5-烯化物基本上相同。用庚烯酸和辛烯酸可获得可比的结果。这些酸在三氟乙酸酐存在下的分子内酰化作用取决于酸的结构和立体化学。据报道，由庚6-烯酸形成环庚-2-烯酮。显示出乙酸酐中的浓硫酸分别将六烯酸和庚烯五烯酸转化为苯基乙酸酯和邻甲苯基乙酸酯。据报道，链烯酸的一些改进的合成。

  DOI：

  10.1039/j39680000217
• 作为产物：
  描述：

  庚-5-炔-1-醇 生成 1-cyano-5-heptyne
  参考文献：
  名称：

  Oxidative cyclization of .delta.,.epsilon.- and .epsilon.,.zeta.-unsaturated enol silyl ethers and unsaturated siloxycyclopropanes

  摘要：

  Oxidative cyclization of delta,epsilon- and epsilon,zeta-unsaturated enol silyl ethers 4a and 4b with cupric triflate and cuprous oxide or ceric ammonium nitrate and sodium bicarbonate in acetonitrile provides the tricyclic ketones 5a and 5b stereoselectively. These cyclizations proceed by oxidation of 4 to the cation radical 24 followed by cyclization of 24 to cation radical 27. This cation radical undergoes a second cyclization to give cation radical 30, which loses the silyl group, undergoes a second oxidation, and loses a proton to give 5. The stereochemistry of the cycloadduct is controlled by the stereochemistry of the enol ether. The Z-enol methyl ether (Z)-65 leads mainly to 5a while the E-enol methyl ether (E)-65 leads mainly to 6a. The oxidative cyclizations of 7, 13, 21, and 43 are also described. Oxidation of alpha-allyl silyl enol ethers 34a and 34b leads mainly to oxidation without cyclization to give the alpha,beta-unsaturated ketones 36a and 36b. Oxidative cyclizations of alkynyl silyl enol ethers 56 and 60 lead to 15 and 64, respectively. Oxidation of siloxycyclopropane 74 with Cu(BF4)2 generates cation radical 75, which cyclizes to 76, which is oxidized to give 21% of cyclopentane 77. This suggests that cation radicals are intermediates in the oxidative dimerization of siloxycyclopropanes.

  DOI：

  10.1021/jo00034a038

文献信息

• Metallacycle Transfer from Zirconium to Main Group Elements: A Versatile Synthesis of Heterocycles
  作者：Paul J. Fagan、William A. Nugent、Joseph C. Calabrese

  DOI：10.1021/ja00084a031

  日期：1994.3

  The reaction of zirconium metallacycles is used to produce a variety of main group heterocycles including borole Diels-Alder dimers, galloles, indacyclopentadienes, siloles, germoles, stannoles, phospholes, arsoles, stiboles, bismoles, thiophenes, selenophenes, dihydrothiophenes, dihydroselenophenes, tetrahydrothiophenes, tetrahydroselenophenes, stannacyclopentanes, phospholenes, and isothiazoles.

  锆金属环的反应用于生产各种主族杂环，包括硼醇 Diels-Alder 二聚体、galloles、indacyclopentadienes、siloles、germoles、stannoles、phospholes、arsoles、stiboles、bismoles、噻吩、硒代四氢噻吩、二氢噻吩、二氢噻吩、四氢硒酚、锡环戊烷、磷烯和异噻唑。讨论了 1-苯基-2,3,4,5-四甲基硼的硼醇 Diels-Alder 二聚体的 X 射线晶体学研究，并与 7-降冰片烯基碳鎓离子的结构进行了比较。描述了这种金属环转移反应的范围和潜力
• [EN] MACROCYCLIC LACTONES AS FRAGRANCES<br/>[FR] COMPOSÉS ORGANIQUES
  申请人：GIVAUDAN SA

  公开号：WO2009039675A1

  公开（公告）日：2009-04-02

  The present invention refers to methyl-substituted double-unsaturated macrocyclic lactones comprising 14 to 17 ring atoms of formula (I) wherein n and m are independently selected from 1, 2, 3 and 4 with the proviso that 3 ≤ n + m ≤ 6. The invention relates furthermore to their use as odorant and fragrance composition comprising them.

  本发明涉及一种具有14到17个环原子的甲基取代双不饱和大环内酯，其化学式为（I），其中n和m分别选自1、2、3和4，但需满足3 ≤ n + m ≤ 6。该发明还涉及它们作为气味剂和香精组合物的用途。
• (4<i>E</i>,8<i>Z</i>)-12-Methyloxacyclotetradeca-4,8-dien-2-one and Its 7a-Homologue: Conformationally Constrained Double-Unsaturated Macrocyclic Musks by Ring-Closing Alkyne Metathesis
  作者：Philip Kraft、Carola Berthold

  DOI：10.1055/s-2008-1032135

  日期：2008.2

  The double-unsaturated macrocyclic lactones (4 E,8 Z)-12-methyloxacyclotetradeca-4,8-dien-2-one and its 7a-homologue (4 E,9 Z)-13-methyloxacyclopentadeca-4,9-dien-2-one, designed as new potent musk odorants by molecular modeling, were synthesized by ring-closing alkyne metathesis in the presence of 10 mol% of Schrock’s alkylidyne catalyst, and subsequent Lindlar hydrogenation. Demethylation of citronellol

  双不饱和大环内酯 (4 E,8 Z)-12-methyloxacyclopentadeca-4,8-​​dien-2-one 及其 7a-同系物 (4 E,9 Z)-13-methyloxacyclopentadeca-4,9-dien- 2-one 是通过分子模型设计为新型强效麝香气味剂，通过在 10 mol% 的 Schrock 烷撑催化剂存在下闭环炔烃复分解和随后的 Lindlar 氢化合成。由亚硝酸诱导的香茅醇去甲基化提供了 3-methyloct-6-yn-1-ol 结构单元。炔烃复分解的底物是通过香茅醇与 3 E 配置的非 3-en-7-ynoic 酸和 dec-3-en-8-ynoic 酸的 Steglich 酯化制备的，可通过 β,γ-选择性 Knoevenagel 缩合获得相应的炔烃 hept-5-ynal 和 oct-6-ynal，它们分别通过 2-甲基环己-2-烯酮的环氧化物的
• Synthesis of main group heterocycles by metallacycle transfer from zirconium
  作者：Paul J. Fagan、William A. Nugent

  DOI：10.1021/ja00215a057

  日期：1988.3
• Newman; Wotiz, Journal of the American Chemical Society, 1949, vol. 71, p. 1294
  作者：Newman、Wotiz

  DOI：——

  日期：——