(1R,2R)-1-fluoro-3-phenyl-2-propanol | 114181-12-3

• 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: (1R,2R)-1-fluoro-3-phenyl-2-propanol
• 英文别名: (R,R)-1-fluoro-1-phenylpropan-2-ol；(1R,2R)-1-Fluoro-1-phenyl-propan-2-ol；(1R,2R)-1-fluoro-1-phenylpropan-2-ol
• CAS: 114181-12-3
• 化学式: C₉H₁₁FO
• 分子量: 154.184
• InChiKey: AAAFRBMMBSPWKX-APPZFPTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 (1R,2R)-1-fluoro-3-phenyl-2-propanol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  β-Fluoroamphetamines via the Stereoselective Synthesis of Benzylic Fluorides

  摘要：

  A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3 center dot OEt2 in CH2Cl2 at -20 degrees C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective S(N)1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted beta-fluoroamphetamines.

  DOI：

  10.1021/ol100862s
• 作为产物：
  描述：

  1(1R,2R)-(+)-1-苯基亚丙基环氧 在 三氟化硼乙醚 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以81%的产率得到(1R,2R)-1-fluoro-3-phenyl-2-propanol
  参考文献：
  名称：

  β-Fluoroamphetamines via the Stereoselective Synthesis of Benzylic Fluorides

  摘要：

  A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3 center dot OEt2 in CH2Cl2 at -20 degrees C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective S(N)1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted beta-fluoroamphetamines.

  DOI：

  10.1021/ol100862s

文献信息

• Dehydrogenation Based Asymmetric Epoxidation of Arylalkanes to Chiral Epoxides
  作者：Yiting Su、Feng Yu、Guixia Liu、Zheng Huang

  DOI：10.1002/cjoc.202200304

  日期：2022.10

  We report herein a formal asymmetric epoxidation of arylalkanes enabled by a one-pot dual-catalysts system comprising a pincer Ir catalyst for alkane dehydrogenation-alkene isomerization (AD-ISO) and a chiral ketone catalyst for asymmetric alkene epoxidation. This protocol provides a catalytic method for the synthesis of aryl epoxides in useful yields with high regio- and stereoselectivity directly

  我们在此报道了一种通过一锅双催化剂系统实现的芳基烷烃的正式不对称环氧化，该系统包括用于烷烃脱氢-烯烃异构化 (AD-ISO) 的钳形 Ir 催化剂和用于不对称烯烃环氧化的手性酮催化剂。该协议提供了一种催化方法，用于直接从容易获得的烷基芳烃中合成具有高区域和立体选择性的有用产率的芳基环氧化物。环氧化产物的立体特异性衍生允许获得各种对映体富集的化合物。
• Bravo, Pierfrancesco; Piovosi, Elena; Resnati, Giuseppe, Journal of Chemical Research, Miniprint, 1989, # 5, p. 1115 - 1147
  作者：Bravo, Pierfrancesco、Piovosi, Elena、Resnati, Giuseppe

  DOI：——

  日期：——
• An efficient approach to enantiomerically pure fluorhydrins
  作者：Pierfrancesco Bravo、Giuseppe Resnati

  DOI：10.1016/s0040-4039(00)96646-2

  日期：1987.1
• SHIMIZU, MAKOTO;YOSHIOKA, HIROSUKE, TETRAHEDRON LETT., 29,(1988) N 33, C. 4101-4104
  作者：SHIMIZU, MAKOTO、YOSHIOKA, HIROSUKE

  DOI：——

  日期：——
• β-Fluoroamphetamines via the Stereoselective Synthesis of Benzylic Fluorides
  作者：Alexander J. Cresswell、Stephen G. Davies、James A. Lee、Paul M. Roberts、Angela J. Russell、James E. Thomson、Melloney J. Tyte

  DOI：10.1021/ol100862s

  日期：2010.7.2

  A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3 center dot OEt2 in CH2Cl2 at -20 degrees C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective S(N)1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted beta-fluoroamphetamines.