(R)-non-3-yn-2-ol | 112780-06-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-non-3-yn-2-ol
• 英文别名: (2R)-non-3-yn-2-ol
• CAS: 112780-06-0
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: NFCFRJFSBOSNOX-SECBINFHSA-N

物化性质

• 沸点：
  166.3±8.0 °C(Predicted)
• 密度：
  0.885±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (R)-non-3-yn-2-ol 在 正丁基锂 、 三氟化硼乙醚 、 potassium tert-butylate 、 lithium 、 1,3-丙二胺 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 环己烷 、 甲苯 为溶剂， 反应 50.5h， 生成 (2R,6E,8E,12S,14Z,16E,18S)-12-(tert-butyldimethylsilyloxy)-18-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)henicosa-6,8,14,16,20-pentaen-10-one
  参考文献：
  名称：

  Synthetic Studies on Macrolactin A: Construction of C4−C24 Fragment

  摘要：

  The preparation of the C4-C24 fragment of the macrolactin A is described. The adopted synthetic strategy involves two isomerizations to selectively construct the (8E,10Z) and (16E,18E) dienes, using a sequential Claisen rearrangement/allene isomerization and a Ph3P-catalyzed isomerization of an yne-one, respectively.

  DOI：

  10.1021/jo0701942
• 作为产物：
  描述：

  1-庚炔 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 氢氧化钾 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 异丙醇 为溶剂， 反应 41.0h， 生成 (R)-non-3-yn-2-ol
  参考文献：
  名称：

  Synthetic Studies on Macrolactin A: Construction of C4−C24 Fragment

  摘要：

  The preparation of the C4-C24 fragment of the macrolactin A is described. The adopted synthetic strategy involves two isomerizations to selectively construct the (8E,10Z) and (16E,18E) dienes, using a sequential Claisen rearrangement/allene isomerization and a Ph3P-catalyzed isomerization of an yne-one, respectively.

  DOI：

  10.1021/jo0701942

文献信息

• Highly enantioselective propargylic monofluorination established by carbon-13 and fluorine-19 NMR in chiral liquid crystals
  作者：Valérie Madiot、Danielle Grée、René Gree、Philippe Lesot、Jacques Courtieu

  DOI：10.1039/a909012f

  日期：——

  Carbon-13 and fluorine-19 NMR experiments in a chiral polypeptide liquid crystalline solvent (PBLG) are used to establish enantioselective propargylic monofluorination.

  手性多肽液晶溶剂 (PBLG) 中的碳 13 和氟 19 NMR 实验用于建立对映选择性炔丙基单氟化。
• Synthesis of a Fluorous Ligand and Its Application for Asymmetric Addition of Dimethylzinc to Aldehydes
  作者：Yasser S. Sokeirik、Hiroyuki Mori、Masaaki Omote、Kazuyuki Sato、Atsushi Tarui、Itsumaro Kumadaki、Akira Ando

  DOI：10.1021/ol070466n

  日期：2007.5.1

  A new fluorous ligand was synthesized from the acetonide of dimethyl tartarate, which showed excellent asymmetric induction on the addition of dimethylzinc to aldehydes. This ligand will be useful for synthesis of bioactive compounds with a methyl carbinol moiety. It could be recycled without using a fluorous solvent or a fluorous column.
• Selective reductions. 46. Effect of the steric requirement at the 2-position of apopinene on chiral reductions. B-(iso-2-ethylapopinocampheyl)- and B-(iso-2-n-propylapopinocampheyl)-9-borabicyclo[3.3.1]nonanes as improved reagents for the chiral reduction of .alpha.,.beta.-acetylenic ketones and .alpha.-keto esters
  作者：Herbert C. Brown、P. Veeraraghavan Ramachandran、Steven A. Weissman、S. Swaminathan

  DOI：10.1021/jo00313a020

  日期：1990.12

  B-(Iso-2-ethylapopinocampheyl)-9-borabicyclo[3.3.1]nonane (Eapine-Borane, 7), and B-(Iso-2-n-propylapopinocampheyl)-9-borabicyclo[3.3.1]nonane (Prapine-Borane, 9), prepared via the hydroboration of 2-ethylapopinene (6) or 2-n-propylapopinene (8), respectively, with 9-borabicyclo[3.3.1]nonane, reduce prochiral alpha,beta-acetylenic ketones and alpha-keto esters to the corresponding alcohols with significantly higher optical induction than does Alpine-Borane (1). (-)-2-n-Propylapopinene was synthesized by treating nopyl tosylate with dimethyl cuprate prepared in situ from ethyllithium and cuprous iodide. (+)-2-n-Propylapopinene was synthesized by Schlosser metalation of (+)-alpha-pinene followed by treatment with ethyl iodide. 4-Phenyl-3-butyn-2-one was reduced to the corresponding propargylic alcohol in 89% ee and 96% ee by Eapine-Borane and Prapine-Borane, respectively, as compared to 82% ee with Alpine-Borane. Similar improved results were realized in the reduction of other acetylenic ketones by Eapine-Borane and Prapine-Borane. Similar improvements in the optical yields were realized in the reduction of alpha-keto esters by Eapine-Borane. For example, while Alpine-Borane produced methyl and ethyl lactate in 92% and 91% ee, respectively, Eapine-Borane gave these alcohols in 97% and 96% ee, respectively. Unfortunately, Prapine-Borane shows no improvement in percent ee for the reduction of alpha-keto esters. The increase in the percent ee realized is tentatively attributed to the increased steric requirements of the alkyl group at the 2-position of apopinene.
• Direct Catalytic Enantioselective Reduction of Achiral α,β-Ynones. Strong Remote Steric Effects Across the C−C Triple Bond
  作者：Christopher J. Helal、Plato A. Magriotis、E. J. Corey

  DOI：10.1021/ja962849e

  日期：1996.1.1