(S)-5-methyl-3-hexyn-2-ol | 129364-64-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-5-methyl-3-hexyn-2-ol
• 英文别名: 5-methyl-3-hexyn-2-ol；(2S)-5-methylhex-3-yn-2-ol
• CAS: 129364-64-3
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: PTDRERHMUFABMH-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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)-5-methyl-3-hexyn-2-ol 在 喹啉 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 168.0h， 生成 (S,Z)-2-[(diisopropylamino)carbonyloxy]-5-methyl-3-hexene
  参考文献：
  名称：

  使用锂化烯丙基氨基甲酸酯通过类卡宾消除交叉偶联立体有择合成共轭二烯

  摘要：

  掌控之中！对映体富集的锂化烯丙基氨基甲酸酯和对映体富集的α-氨基甲酰氧基烷基硼酸酯之间的消除交叉偶联提供了 1,2,4-三取代的 1,3-丁二烯的立体有择合成。共轭二烯产物的任何几何异构体都可以通过类卡宾底物中的立体化学构型和触发的消除机制类型（顺式或反式）的适当组合获得。

  DOI：

  10.1002/ejoc.202101011
• 作为产物：
  描述：

  (±)-5-methyl-3-hexyn-2-ol 在 丁二酸酐 、 PS-Amano lipase 作用下， 以 乙醚 为溶剂， 反应 7.0h， 以48%的产率得到(S)-5-methyl-3-hexyn-2-ol
  参考文献：
  名称：

  使用锂化烯丙基氨基甲酸酯通过类卡宾消除交叉偶联立体有择合成共轭二烯

  摘要：

  掌控之中！对映体富集的锂化烯丙基氨基甲酸酯和对映体富集的α-氨基甲酰氧基烷基硼酸酯之间的消除交叉偶联提供了 1,2,4-三取代的 1,3-丁二烯的立体有择合成。共轭二烯产物的任何几何异构体都可以通过类卡宾底物中的立体化学构型和触发的消除机制类型（顺式或反式）的适当组合获得。

  DOI：

  10.1002/ejoc.202101011

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.
• 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：——
• HETEROCYCLIC KINASE INHIBITORS
  申请人：Ren Pingda

  公开号：US20110281866A1

  公开（公告）日：2011-11-17

  The present invention provides heterocyclic compounds for use as kinase inhibitors and in other applications. Also provided are pharmaceutical compositions and methods of treatments of diseases and conditions associated with P13 kinase activity.
• US9296742B2
  申请人：——

  公开号：US9296742B2

  公开（公告）日：2016-03-29
• US9790228B2
  申请人：——

  公开号：US9790228B2

  公开（公告）日：2017-10-17