(R)-5-methyl-3-hexyn-2-ol | 112780-07-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-5-methyl-3-hexyn-2-ol
• 英文别名: (R)-5-methylhex-3-yn-2-ol；(2R)-5-methylhex-3-yn-2-ol
• CAS: 112780-07-1
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: PTDRERHMUFABMH-SSDOTTSWSA-N

物化性质

• 沸点：
  158.9±8.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)

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：

  (R)-5-methyl-3-hexyn-2-ol 在 aluminum 、 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  季碳结构烯丙基取代合成维拉帕米中间体

  摘要：

  在本研究中，关键的仲烯丙基吡啶甲酸酯是通过 Pd(PPh3)4 催化的 (R,Z)-4-iodo-5-methylhex-3-en-2-ol 的 TBS 醚与烯丙基-溴化镁。吡啶甲酸酯与源自 3,4-(MeO)2C6H3MgBr 和 Cu(acac)2 的铜试剂以 2:1 的比例进行烯丙基取代，得到了具有完全手性转移和 91% 区域选择性的抗 SN2' 产物。烯烃部分的合成操作导致产生腈基，从而产生用于合成 (S)-维拉帕米的中间体。

  DOI：

  10.1055/s-0036-1588518
• 作为产物：
  描述：

  1,1-二溴-3-甲基丁-1-烯 在 正丁基锂 、 [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I) 、 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 (R)-5-methyl-3-hexyn-2-ol
  参考文献：
  名称：

  季碳结构烯丙基取代合成维拉帕米中间体

  摘要：

  在本研究中，关键的仲烯丙基吡啶甲酸酯是通过 Pd(PPh3)4 催化的 (R,Z)-4-iodo-5-methylhex-3-en-2-ol 的 TBS 醚与烯丙基-溴化镁。吡啶甲酸酯与源自 3,4-(MeO)2C6H3MgBr 和 Cu(acac)2 的铜试剂以 2:1 的比例进行烯丙基取代，得到了具有完全手性转移和 91% 区域选择性的抗 SN2' 产物。烯烃部分的合成操作导致产生腈基，从而产生用于合成 (S)-维拉帕米的中间体。

  DOI：

  10.1055/s-0036-1588518

文献信息

• CERTAIN CHEMICAL ENTITIES, COMPOSITIONS AND METHODS
  申请人：INTELLIKINE LLC

  公开号：US20140206684A1

  公开（公告）日：2014-07-24

  Chemical entities that modulate PI3 kinase activity, and chemical entities, pharmaceutical compositions, and methods of treatments of diseases and conditions associated with P13 kinase activity are described herein.

  本文描述了调节PI3激酶活性的化学实体，以及与PI3激酶活性相关的疾病和病状的化学实体、药物组合物和治疗方法。
• 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.
• 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