4-((Prop-2-yn-1-yloxy)methyl)benzonitrile | 77180-30-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-((Prop-2-yn-1-yloxy)methyl)benzonitrile
• 英文别名: 4-(prop-2-ynoxymethyl)benzonitrile
• CAS: 77180-30-4
• 化学式: C₁₁H₉NO
• 分子量: 171.199
• InChiKey: GVQOTZVZHMIRQR-UHFFFAOYSA-N

物化性质

• 熔点：
  62-63 °C
• 沸点：
  307.7±27.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-((Prop-2-yn-1-yloxy)methyl)benzonitrile 在 5,5'-双(二苯基磷)-四氟-二-1,3-苯二氧杂环 、 四(三苯基膦)钯 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 49.0h， 生成 (R)-4-(((1-(diphenylphosphoryl)allyl)oxy)methyl)benzonitrile
  参考文献：
  名称：

  对映选择性钯催化的艾伦与氧化膦的氢膦酰化：获得手性烯丙基氧化膦

  摘要：

  通过钯催化的丙二烯与氧化膦的不对称氢膦酰化，证明了一种高效、通用和原子经济的手性烯丙基氧化膦方案。以高产率（高达 99%）和对映选择性（高达 99% ee）获得了一系列具有多种官能团的手性烯丙基氧化膦。

  DOI：

  10.1002/anie.202112285
• 作为产物：
  描述：

  对甲苯腈 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 sodium 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 生成 4-((Prop-2-yn-1-yloxy)methyl)benzonitrile
  参考文献：
  名称：

  Krishna Moorthy, Journal of the Indian Chemical Society, 1990, vol. 67, # 11, p. 909 - 911

  摘要：

  DOI：

文献信息

• Substituent Effects on Vinyl Radical Cyclizations onto Aryl Rings
  作者：Pier Carlo Montevecchi、Maria Luisa Navacchia

  DOI：10.1021/jo971399l

  日期：1998.2.1

  pi-endo vs pi-exo cyclization as well as the role of stabilization and polar factors has been studied. The substituent effect on the 5-(pi-exo)exo cyclization has been estimated by the relative rate constants, k(R), calculated for several substituents in the 4- and 3-position. Results show that stabilization and polar factors slightly affect the rate of the vinyl radical cyclization onto arene rings, which

  丙炔基苄基醚2a-i的C-1碳上的区域选择性甲苯硫基自由基会生成乙烯基3a-j，主要通过立体选择性5-（pi-endo）exo和5生成甲基硫醚9a-j和甲基醚8a-j。 -（pi-exo）exo环化。另外，还形成了少量的π-内-六元环化产物5a-j和氢提取产物4a-j。研究了5元与6元和pi-endo与pi-exo环化中空间和立体电子因素的作用，以及稳定化和极性因素的作用。已通过相对速率常数k（R）估算了5-（pi-exo）exo环化的取代基效应，该常数是针对4-和3-位的多个取代基计算的。结果表明，稳定度和极性因素对乙烯基自由基在芳烃环上的环化速率有轻微影响，就取代基的性质而言，这似乎是非选择性的。极性效应的性质表明乙烯基自由基的性质略带亲电性。
• Copper-Catalyzed Regio- and Stereoselective Three-Component Coupling of Allenyl Ethers with <i>gem</i>-Dichlorocyclobutenones and B₂pin₂
  作者：Shuai Liu、Yi-Sen Qian、Jian-Lin Xu、Lei Xu、Yun-He Xu

  DOI：10.1021/acs.orglett.3c01515

  日期：2023.6.23

  and stereoselective difunctionalization of allenes with allenyl ethers, bis(pinacolato)diboron, and gem-dichlorocyclobutenones as electrophiles was reported, yielding a variety of highly functionalized cyclobutenone products tethering with an alkenylborate fragment. The polysubstituted cyclobutenone products also underwent diverse transformations.

  报道了用丙二烯基醚、双(频哪醇)二硼和偕二氯环丁烯酮作为亲电子试剂对丙二烯进行区域和立体选择性双官能化的三组分偶联方法，产生了多种与烯基硼酸酯片段束缚的高度官能化的环丁烯酮产物。多取代环丁烯酮产品也经历了多样化的转变。
• Visible-Light-Initiated Sequential Trifluoromethylation/Remote C(sp³)–H Alkynylation of Vinyl Azides by Radical Relay
  作者：Zirui Chen、Yunnan Duan、Shitao Sun、Bin Lin、Xiaozu Liu、Peijun Liu

  DOI：10.1021/acs.joc.3c00170

  日期：——

  α-alkyl-substituted vinyl azides using acetylenic triflones as both the trifluoromethyl and alkyne donors is described. The reaction occurred under environmentally benign and radical initiator-free reaction conditions, affording γ-alkynylated trifluoromethyl ketone derivatives with a broad scope of substituents. Mechanistic studies suggested that the reaction is initiated via a triplet–triplet energy transfer between

  描述了使用乙炔三氟酮作为三氟甲基和炔烃供体的可见光引发的 α-烷基取代乙烯基叠氮化物的三氟甲基化/远程脂肪族 C-H 炔基化。该反应在环境友好且无自由基引发剂的反应条件下发生，得到具有广泛取代基的 γ-炔基化三氟甲基酮衍生物。机理研究表明，该反应是通过4CzIPN 催化剂和炔基三氟甲磺酮之间的三重态-三重态能量转移引发的，然后裂解产生三氟甲基自由基和炔基自由基。
• Benzylpropargylether as nitrification inhibitors
  申请人：BASF SE

  公开号：US11021413B2

  公开（公告）日：2021-06-01

  The present invention relates to the use of compounds of formula (I) for reducing nitrification and to compositions comprising the compounds of formula (I) and to agricultural mixtures comprising at least one compound of formula (I) and at least one fertilizer. Furthermore, the present invention relates to a method for reducing nitrification comprising treating a plant growing on soil or soil substituents and/or the locus or soil or soil substituents where the plant is growing or is intended to grow with a compound of formula (I) or a composition comprising a compound of formula (I).

  本发明涉及式(I)化合物用于降低硝化的用途，涉及包含式(I)化合物的组合物，涉及包含至少一种式(I)化合物和至少一种肥料的农用混合物。此外，本发明还涉及一种降低硝化作用的方法，该方法包括用式（I）化合物或包含式（I）化合物的组合物处理生长在土壤或土壤亚基上的植物和/或植物生长或打算生长的地点或土壤或土壤亚基。
• Stereoselective Cyclizations and Rearrangements in Vinyl Radicals Promoted by Regioselective Sulfanyl Radical Addition to Enynes
  作者：Pier Carlo Montevecchi、Maria Luisa Navacchia

  DOI：10.1021/jo9701142

  日期：1997.8.1

  Regioselective radical addition of 4-cyanotoluenethiol (1a) to enynes 3-6 leads to vinyl radicals 7-10 that can undergo five- or six-membered cyclization onto styrene or terminal double bonds in competition with 5-exo cyclization onto the aryl ring, The latter affords spiro-cyclohexadienyl radical intermediates which can either be trapped by 2-cyanoisopropyl radicals or give 1,4-aryl migration products. Regioselective radical addition of phenethanethiol (1b) to enynes 3-6 gives radicals 11-14 which undergo five- or six-membered cyclization onto the alkene double bond; the stereoelectronically disfavored 6-exo cyclization can compete with intermolecular hydrogen abstraction and (to a small extent) with 1,5-hydrogen migration. The 5- and 6-(pi-exo)exo cyclization of vinyl radicals 7, 9, 11-13 is highly stereoselective and exclusively or predominately affords products deriving from the (Z)-isomers. Stereochemical evidence indicates that the six-membered endo-cyclization products 30 and 50 could derive from a direct 6-endo cyclization of (E)-radicals (E)-10 and (E)-14 rather than from a 5-exo cyclization/ring expansion process. Sulfanyl radical addition to enynes 3-5 is highly regioselective to the terminal triple bond. In contrast, reaction elf thiols 1a,b with enyne 6 leads to products deriving from sulfanyl radical addition to both the CC triple and double bond. This behavior is accounted for by assuming that sulfanyl radical addition to the alkyne triple bond is not reversible, while the addition to the alkene double bond is. Vinyl radical 10 affords product 33 by a rare 1,4-hydrogen migration/fragmentation process.