(1R,2S)-2-庚-1-炔基环己烷-1-醇 | 54623-33-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R,2S)-2-庚-1-炔基环己烷-1-醇
• 英文名称: 2₁-(E,1-heptynyl)-1-cyclohexanol
• 英文别名: (1RS,2SR)-2-(pentylethynyl)cyclohexanol；1r-Hydroxy-2t-heptin-(1)-yl-cyclohexan；2-(1-Heptinyl)-cyclohexanol；(1R,2S)-2-(Hept-1-yn-1-yl)cyclohexan-1-ol；(1R,2S)-2-hept-1-ynylcyclohexan-1-ol
• CAS: 54623-33-5；86100-11-0；138907-22-9
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: KSRINXHLVZQFRA-CHWSQXEVSA-N

物化性质

• 沸点：
  298.8±29.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 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,2S)-2-庚-1-炔基环己烷-1-醇 在 偶氮二异丁腈 、 (PhO)3P*Br₂ 、 三苯基氢化锡 作用下， 以 乙醚 、 苯 为溶剂， 反应 14.0h， 生成 3-hexylidene-1,2,3a,4,5,6,7,7a-octahydroindene-2-carbonitrile
  参考文献：
  名称：

  Angoh, Gaeatan A.; Clive, Derrick L. J., Journal of the Chemical Society. Chemical communications, 1985, # 14, p. 980 - 982

  摘要：

  DOI：
• 作为产物：
  描述：

  1-庚炔 、 氧化环己烯 生成 (1R,2S)-2-庚-1-炔基环己烷-1-醇
  参考文献：
  名称：

  三烷基炔基硼酸锂与环氧乙烷的反应：γ-羟基酮的合成和三取代乙烯的立体选择性制备

  摘要：

  三烷基炔基硼酸锂（1）与环氧乙烷（2）反应生成不可分离的中间体3，随后经NaOH / H 2 O 2适当处理，可得到γ-羟基酮5，均烯丙基醇类型6的三取代乙烯或四取代乙烯7，分别为AcOH或NaOH / I 2。环氧乙烷与1的反应以高区域选择性进行，并且所得到的均烯丙基醇6具有接近100％（E）构型。直链γ-羟基酮16在甲氧基环氧乙烷与由乙炔化乙二胺锂络合物和三己基硼烷制得的酯络合物（1）的反应中获得了β-环糊精。

  DOI：

  10.1016/s0040-4020(01)97550-7

文献信息

• Boron trifluoride assisted opening of epoxides by lithium alkenyl aluminate reagents
  作者：A. Alexakis、D. Jachiet

  DOI：10.1016/s0040-4020(01)85130-9

  日期：1989.1

  Alkenyl aluminate reagents, obtained by hydroalumination of terminal alkynes followed by ate complexation with Meli, react readily with poorly reactive cyclic ethers such as cyclohexene oxide and oxetane, in the presence of BF3·Et2O. Alkenyl aluminate reagents obtained by reaction of an alkenyl tithium reagent and Me3Al behave similarly.

  通过在末端BF 3 ·Et 2 O的存在下，通过末端炔烃的加氢铝化反应，然后与Meli进行络合而获得的链烯铝酸盐试剂容易与反应性较弱的环醚（如环氧乙烷和氧杂环丁烷）反应。烯基钛试剂和Me 3 Al的行为相似。
• The reaction of lithium trialkylalkynylborates with oxiranes
  作者：M. Naruse、K. Utimoto、H. Nozaki

  DOI：10.1016/s0040-4020(01)97550-7

  日期：1974.1

  Lithium trialkylalkynylborates (1) react with oxiranes (2) to give non-isolable intermediates 3 which subsequently afford either γ-hydroxyketones 5, trisubstituted ethylenes of homoallylic alcohol type 6 or a tetrasubstituted ethylene 7 upon appropriate treatment with NaOH/H2O2, AcOH or NaOH/I2, respectively. The reaction of oxiranes with 1 proceeds in high regioselectivity and the resulting homoallylic

  三烷基炔基硼酸锂（1）与环氧乙烷（2）反应生成不可分离的中间体3，随后经NaOH / H 2 O 2适当处理，可得到γ-羟基酮5，均烯丙基醇类型6的三取代乙烯或四取代乙烯7，分别为AcOH或NaOH / I 2。环氧乙烷与1的反应以高区域选择性进行，并且所得到的均烯丙基醇6具有接近100％（E）构型。直链γ-羟基酮16在甲氧基环氧乙烷与由乙炔化乙二胺锂络合物和三己基硼烷制得的酯络合物（1）的反应中获得了β-环糊精。
• Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates
  作者：Mario D. Bachi、Eric Bosch

  DOI：10.1021/jo00043a030

  日期：1992.8

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.
• An efficient method for the alkynylation of oxiranes using alkynyl boranes
  作者：Masahiko Yamaguchi、Ichiro Hirao

  DOI：10.1016/s0040-4039(00)81416-1

  日期：——
• Stereo- and regioselective metal salt-catalyzed alkynylation of 1,2-epoxides
  作者：Marco Chini、Paolo Crotti、Lucilla Favero、Franco Macchia

  DOI：10.1016/0040-4039(91)80237-z

  日期：1991.11

  A simple, efficient, stereoselective, and highly regioselective method for the synthesis of beta-hydroxyacetylenes by the direct opening of 1,2-epoxides with lithium acetylides in anhydrous THF, in the presence of metal salts, is described. This new method appears to be competitive and alternative to the other methods previously reported.