(S)-3-(benzyloxy)pent-4-yn-1-ol | 1384132-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-(benzyloxy)pent-4-yn-1-ol
• 英文别名: (3S)-3-phenylmethoxypent-4-yn-1-ol
• CAS: 1384132-59-5
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: ZTUUWXNJABFQPJ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(benzyloxy)pent-4-yn-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四溴化碳 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (S)-1-(3-(benzyloxy)-5-bromopent-1-ynyl)-2-methoxybenzene
  参考文献：
  名称：

  Modular and Stereoselective Synthesis of Tetrasubstituted Helical Alkenes via a Palladium-Catalyzed Domino Reaction

  摘要：

  A highly modular and stereoselective synthesis of tetrasubstituted helical alkenes is accomplished by a Pd-catalyzed norbornene-mediated domino reaction. This protocol features the rapid assembly of four C-C bonds via sequential C-H activations and carbopalladations along with efficient access to enantiopure bromoalkyl aryl alkyne precursors using homologative alkynylation as the key transformation. Three distinct elements of stereoselectivity were observed in the preparation of the chiral helical alkenes: retention of stereochemistry of the substrates, induced helical diastereoselectivity in the alkene formation, and the exclusive exo-facial selectivity of the norbornene incorporation.

  DOI：

  10.1021/ol301495q
• 作为产物：
  描述：

  (S)-3-(benzyloxy)dihydrofuran-2(3H)-one 在 正丁基锂 、 四丁基氟化铵 、 二异丁基氢化铝 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (S)-3-(benzyloxy)pent-4-yn-1-ol
  参考文献：
  名称：

  Modular and Stereoselective Synthesis of Tetrasubstituted Helical Alkenes via a Palladium-Catalyzed Domino Reaction

  摘要：

  A highly modular and stereoselective synthesis of tetrasubstituted helical alkenes is accomplished by a Pd-catalyzed norbornene-mediated domino reaction. This protocol features the rapid assembly of four C-C bonds via sequential C-H activations and carbopalladations along with efficient access to enantiopure bromoalkyl aryl alkyne precursors using homologative alkynylation as the key transformation. Three distinct elements of stereoselectivity were observed in the preparation of the chiral helical alkenes: retention of stereochemistry of the substrates, induced helical diastereoselectivity in the alkene formation, and the exclusive exo-facial selectivity of the norbornene incorporation.

  DOI：

  10.1021/ol301495q

文献信息

• Expeditious Synthesis of Tetrasubstituted Helical Alkenes by a Cascade of Palladium-Catalyzed CH Activations
  作者：Hongqiang Liu、Mohamed El-Salfiti、Mark Lautens

  DOI：10.1002/anie.201204226

  日期：2012.9.24

  Twisted molecules: A modular approach for the synthesis of tetrasubstituted helical alkenes by a palladium‐catalyzed norbornene‐mediated domino reaction is presented. This intermolecular domino process allows the formation of three CC bonds in one operation through a CH activation/carbopalladation/CH activation sequence.

  扭曲分子：提出了一种通过钯催化的降冰片烯介导的多米诺反应合成四取代螺旋烯烃的模块化方法。此分子间多米诺过程允许的三个C的形成在一个操作中C键通过C  ħ激活/ carbopalladation / C  ħ激活序列。