(S)-1-(benzyloxy)-4-phenylbutan-2-ol | 1359976-85-4

• 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)-1-(benzyloxy)-4-phenylbutan-2-ol
• 英文别名: (2S)-1-(benzyloxy)-4-phenylbutan-2-ol；(2S)-4-phenyl-1-phenylmethoxybutan-2-ol
• CAS: 1359976-85-4
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: OCUVISZQCCNAME-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-苄氧甲基环氧乙烷 、 苄基氯化镁 在 copper(l) chloride 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.0h， 以97%的产率得到(S)-1-(benzyloxy)-4-phenylbutan-2-ol
  参考文献：
  名称：

  Development of a Robust Procedure for the Copper-catalyzed Ring-Opening of Epoxides with Grignard Reagents

  摘要：

  A general procedure for the copper-catalyzed regioselective ring-opening of epoxides with Grignard reagents is described. The procedure developed provides robust reaction conditions which limit the formation of impurities and has been applied successfully using a series of epoxides and Grignard reagents to provide the desired products in >90% yield with excellent regioselectivity and purity.

  DOI：

  10.1021/op200329x

文献信息

• Continuous Flow Preparation of Benzylic Sodium Organometallics
  作者：Johannes H. Harenberg、Rajasekar Reddy Annapureddy、Konstantin Karaghiosoff、Paul Knochel

  DOI：10.1002/anie.202203807

  日期：2022.7.25

  A lateral sodiation of alkyl(hetero)arenes using on-demand generated (2-ethylhexyl)sodium in the presence of TMEDA is reported. Various electrophiles were used for trapping of the benzyl sodium species generated in continuous flow as well as in batch. The continuous flow metalation was scaled-up using an in-line quench. The method was used in the synthesis of several industrial relevant compounds.

  据报道，在 TMEDA 存在下，使用按需生成的 (2-乙基己基)钠对烷基（杂）芳烃进行横向钠化。使用各种亲电子试剂来捕获连续流动以及批量产生的苄基钠物质。使用在线淬火放大连续流金属化。该方法用于多种工业相关化合物的合成。
• Development of a Robust Procedure for the Copper-catalyzed Ring-Opening of Epoxides with Grignard Reagents
  作者：Mahbub Alam、Christopher Wise、Carl A. Baxter、Ed Cleator、Andrew Walkinshaw

  DOI：10.1021/op200329x

  日期：2012.3.16

  A general procedure for the copper-catalyzed regioselective ring-opening of epoxides with Grignard reagents is described. The procedure developed provides robust reaction conditions which limit the formation of impurities and has been applied successfully using a series of epoxides and Grignard reagents to provide the desired products in >90% yield with excellent regioselectivity and purity.