(1R)-2-ethynyl-1,7,7-trimethyl-norbornane-2endo-ol | 22387-58-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R)-2-ethynyl-1,7,7-trimethyl-norbornane-2endo-ol
• 英文别名: HCC-2-borneol；(1R)-2-Aethinyl-1,7,7-trimethyl-norbornan-2endo-ol；2-Ethynylisoborneol；(1R,2R,4R)-2-ethynyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 22387-58-2
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: AXIWZGXZGAUBSU-JLLWLGSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R)-2-ethynyl-1,7,7-trimethyl-norbornane-2endo-ol 在 N-碘代丁二酰亚胺 、 hydroxy(tosyloxy)iodobenzene 、 碘 、 silver nitrate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 18.0h， 生成 2--1,8,8-trimethylbicyclo<3.2.1>octan-3-one
  参考文献：
  名称：

  Ring Expansions of 2-Haloethynyl-2-norbornanols

  摘要：

  2-Haloethynyl-2-norbomanols react with iodine and Koser's reagent in acetonitrile to afford two ring-expanded products, 2-[(Z)-haloiodomethylidene]bicyclo[3.2.1]octan-3-one and 3-[(Z)-haloiodomethylidene]bicyclo[3.2.1]octan-2-one. These results contrast with the 2-haloethynyl-2-bomanols which lead to the corresponding 3-octanones.

  DOI：

  10.1016/s0040-4020(01)89294-2
• 作为产物：
  描述：

  (1R,2S,4R)-2-ethynyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 在 N-甲基吡咯烷酮 、 氢氧化钾 、 乙炔 作用下， 生成 (1R)-2-ethynyl-1,7,7-trimethyl-norbornane-2endo-ol
  参考文献：
  名称：

  Capmau,M.-L. et al., Bulletin de la Societe Chimique de France, 1968, p. 3233 - 3238

  摘要：

  DOI：

文献信息

• Isolable Gold(I) Complexes Having One Low-Coordinating Ligand as Catalysts for the Selective Hydration of Substituted Alkynes at Room Temperature without Acidic Promoters
  作者：Antonio Leyva、Avelino Corma

  DOI：10.1021/jo802558e

  日期：2009.3.6

  Hydration of a wide range of alkynes to the corresponding ketones has been afforded in high yields at room temperature by using gold(I)−phosphine complexes as catalyst, with no acidic cocatalysts required. Suitable substrates covering alkyl and aryl terminal alkynes, enynes, internal alkynes, and propargylic alcohols, including enantiopure forms, are cleanly transformed to the corresponding ketones

  通过使用金（I）-膦配合物作为催化剂，无需酸性助催化剂，即可在室温下高收率地将各种炔烃水合为相应的酮。覆盖烷基和芳基末端炔烃，烯炔，内部炔烃和炔丙醇的合适底物，包括对映体纯形式，以接近定量的收率干净地转化为相应的酮。保留存在于底物中的酸不稳定基团。催化活性强烈取决于与金（I）中心配位的膦的性质以及抗衡阴离子AuSPhosNTf 2的柔软度显示更好的活动。在动力学研究的基础上，提出了一种可行的炔烃通过缩酮中间体水合的机理。所描述的催化系统应提供基于汞的方法的有效替代方法，并在合成程序中有用。
• Ring expansion of an α-bromoalkynol camphor by means of iodine and Koser's reagent
  作者：Pakorn Bovonsombat、Edward McNelis

  DOI：10.1016/s0040-4039(00)79328-2

  日期：1993.7

  The bromoethynyl adduct of camphor was treated with equimolar amounts of iodine and Koser's reagent (HTIB) to afford in good yield and in good stereospecificity a (Z)-bromoiodoenone, a synthon for enantiospecific syntheses.
• Alkynylborneol Derivatives and Their Spatial Structures
  作者：Eckehard V. Dehmlow、Udo Engel、Christiane Woelke

  DOI：10.1002/prac.19963380134

  日期：——
• Prodrugs based on masked lactones. Cyclization of .gamma.-hydroxy amides
  作者：C. David Johnson、Simon Lane、Philip N. Edwards、Peter J. Taylor

  DOI：10.1021/jo00256a040

  日期：1988.10
• Intensely Luminescent Homoleptic Alkynyl Decanuclear Gold(I) Clusters and Their Cationic Octanuclear Phosphine Derivatives
  作者：Igor O. Koshevoy、Yuh-Chia Chang、Antti J. Karttunen、Stanislav I. Selivanov、Janne Jänis、Matti Haukka、Tapani Pakkanen、Sergey P. Tunik、Pi-Tai Chou

  DOI：10.1021/ic300856h

  日期：2012.7.2

  Treatment of Au(SC4H8)Cl with a stoichiometric amount of hydroxyaliphatic alkyne in the presence of NEt3 results in high-yield self-assembly of homoleptic clusters (AuC2R)(10) (R = 9-fluorenol (1), diphenylmethanol (2), 2,6-dimethyl-4-heptanol (3), 3-methyl-2-butanol (4), 4-methyl-2-pentanol (4), 1-cyclohexanol (6), 2-borneol (7)). The molecular compounds contain an unprecedented catenane metal core with two interlocked 5-membered rings. Reactions of the decanuclear clusters 1-7 with gold-diphosphine complex [Au-2(1,4-PPh2-C6H4-PPh2)(2)](2+) lead to octanuclear cationic derivatives [Au-8(C2R)(6)(PPh2-C6H4-PPh2)(2)](2+) (8-14), which consist of planar tetranuclear units Au-4(C2R)(4)} coupled with two fragments [AuPPh2-C6H4-PPh2(AuC2R)](+). The titled complexes were characterized by NMR and ESI-MS spectroscopy, and the structures of I, 13, and 14 were determined by single-crystal X-ray diffraction analysis. The luminescence behavior of both Au-10(I) and Au-8(I) families has been studied, revealing efficient room-temperature phosphorescence in solution and in the solid state, with the maximum quantum yield approaching 100% (2 in solution). DFT computational studies showed that in both Au-10(I) and Au-8(I) clusters metal-centered Au --> Au charge transfer transitions mixed with some pi-alkynyl MLCT character play a dominant role in the observed phosphorescence.