(S)-3-nonyn-2-ol | 129364-63-2

• 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: (S)-3-nonyn-2-ol
• 英文别名: (2S)-non-3-yn-2-ol
• CAS: 129364-63-2
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: NFCFRJFSBOSNOX-VIFPVBQESA-N

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：

  (S)-3-nonyn-2-ol 以 二氯甲烷 为溶剂， 生成 (S)-2-Fluoro-non-3-yne 、 (R)-2-Fluoro-non-3-yne
  参考文献：
  名称：

  手性液晶中通过碳 13 和氟 19 NMR 建立的高对映选择性炔丙基单氟化反应

  摘要：

  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。

  DOI：

  10.1039/a909012f
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到(S)-3-nonyn-2-ol
  参考文献：
  名称：

  手性液晶中通过碳 13 和氟 19 NMR 建立的高对映选择性炔丙基单氟化反应

  摘要：

  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。

  DOI：

  10.1039/a909012f

文献信息

• 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
• BROWN, HERBERT C.;VEERARAGHAVAN, RAMACHANDRAN P.;WEISSMAN, STEVEN A.;SWAM+, J. ORG. CHEM., 55,(1990) N6, C. 6328-6333
  作者：BROWN, HERBERT C.、VEERARAGHAVAN, RAMACHANDRAN P.、WEISSMAN, STEVEN A.、SWAM+

  DOI：——

  日期：——