1-propargyladamantane | 343857-51-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: 1-propargyladamantane
• 英文别名: 1-(Prop-2-yn-1-yl)adamantane；1-prop-2-ynyladamantane
• CAS: 343857-51-2
• 化学式: C₁₃H₁₈
• 分子量: 174.286
• InChiKey: YGMWGIQNYLNHHN-UHFFFAOYSA-N

物化性质

• 沸点：
  235.6±9.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  1-propargyladamantane 在 copper(l) iodide 、 氯[2-(二叔丁基磷)二苯基]金 、 四甲基乙二胺 、 水 、 silver trifluoromethanesulfonate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.5h， 生成 3-(adamantan-1-yl)-1,1,1-trifluoropropan-2-one
  参考文献：
  名称：

  Regioselective Gold-Catalyzed Hydration of CF₃- and SF₅-alkynes

  摘要：

  The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

  DOI：

  10.1021/acs.orglett.9b01379
• 作为产物：
  描述：

  1-金刚烷乙酸 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.5h， 生成 1-propargyladamantane
  参考文献：
  名称：

  Regioselective Gold-Catalyzed Hydration of CF₃- and SF₅-alkynes

  摘要：

  The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

  DOI：

  10.1021/acs.orglett.9b01379

文献信息

• Diamondoid fuels
  申请人：The United States of America, as Represented by the Secretary of the Navy

  公开号：US10710941B1

  公开（公告）日：2020-07-14

  A diamondoid fuel comprising a cage structure including 10, 14, 18, or 22 carbons. The diamondoid fuel also includes one of one to four cyclopropyl groups bonded to the cage structure or two to four functional groups bonded to the cage structure where the functional groups are an alkyl group, an allyl group, a cyclopropyl group, or combinations thereof. Additionally, at least one functional group is an allyl group and at least one functional group is a cyclopropyl group.

  一种含有10、14、18或22个碳原子的笼状结构的金刚烷燃料。该金刚烷燃料还包括一个或多个环丙基基团与笼状结构键合，或者两个到四个功能基团与笼状结构键合，其中功能基团是烷基、烯丙基、环丙基或它们的组合。此外，至少一个功能基团是烯丙基，至少一个功能基团是环丙基。
• Asymmetric Construction of α,γ-Disubstituted α,β-Butenolides Directly from Allylic Ynoates Using a Chiral Bifunctional Phosphine Ligand Enables Cooperative Au Catalysis
  作者：Ting Li、Shicheng Dong、Conghui Tang、Meiling Zhu、Nan Wang、Weiguang Kong、Wenchao Gao、Jun Zhu、Liming Zhang

  DOI：10.1021/acs.orglett.2c01652

  日期：2022.6.24

  construction of chiral γ-substituted α-allyl-α,β-butenolides with up to >99% enantiomeric excess from readily available allylic ynoates is realized. In this asymmetric gold catalysis, the cationic gold(I) catalyst featuring a bifunctional phosphine ligand enables a four-step cascade which permits the conversion of a diverse array of allylic ynoates into valuable chiral α,γ-disubstituted α,β-butenolides.

  实现了高效构建手性 γ-取代的 α-烯丙基-α,β-丁烯内酯，其对映体过量高达 >99%，来自容易获得的烯丙基烯丙基酯。在这种不对称金催化中，具有双功能膦配体的阳离子金 (I) 催化剂可实现四步级联反应，从而允许将多种烯丙基炔酸酯转化为有价值的手性 α,γ-二取代 α,β-丁烯内酯。
• Synthesis of α-Silylmethyl-α,β-Unsaturated Imines by the Rhodium-Catalyzed Silylimination of Primary-Alkyl-Substituted Terminal Alkynes
  作者：Yoshiya Fukumoto、Hiroto Shimizu、Aya Tashiro、Naoto Chatani

  DOI：10.1021/jo501431e

  日期：2014.9.5

  In contrast to our previous report on the rhodium-catalyzed reaction of terminal alkynes with equimolar amounts of hydrosilanes and isocyanides leading to (E)- or (Z)-β-silyl-α,β-unsaturated imines A, the addition of an excess molar amount of hydrosilanes relative to isocyanides in the reaction of primary-alkyl-substituted terminal alkynes results in the production of α-silylmethyl-α,β-unsaturated imines B. Various isocyanides bearing tert-butyl and 1-adamantyl groups gave B with good product selectivity. Z isomers were formed stereoselectively in many cases. Regarding the mechanism for this reaction, when the hydrosilane was added to the reaction mixture in two portions, unsaturated imines A were initially formed, which then underwent double-bond isomerization, probably catalyzed by a Rh-H species, to give B.
• SASAKI, TADASHI;NAKANISHI, AKIRA;OHNO, MASATOMI, J. ORG. CHEM., 1981, 46, 5445-5447
  作者：SASAKI, TADASHI、NAKANISHI, AKIRA、OHNO, MASATOMI

  DOI：——

  日期：——
• SASAKI, TADASHI;NAKANISHI, AKIRA;OHNO, MASATOMI, J. ORG. CHEM., 1982, 47, N 17, 3219-3224
  作者：SASAKI, TADASHI、NAKANISHI, AKIRA、OHNO, MASATOMI

  DOI：——

  日期：——