(2S,3R)-1-chloro-3-phenylpropane-2,3-diol | 139165-55-2

• 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: (2S,3R)-1-chloro-3-phenylpropane-2,3-diol
• 英文别名: (1R,2S)-3-chloro-1-phenylpropane-1,2-diol
• CAS: 139165-55-2
• 化学式: C₉H₁₁ClO₂
• 分子量: 186.638
• InChiKey: UYKRRGHTJOUMLI-RKDXNWHRSA-N

物化性质

• 沸点：
  360.1±37.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3R)-1-chloro-3-phenylpropane-2,3-diol 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以98%的产率得到(1R,2R)-2,3-epoxy-1-phenylpropan-1-ol
  参考文献：
  名称：

  Design and synthesis of (2R,3S)-iodoreboxetine analogues for SPECT imaging of the noradrenaline transporter

  摘要：

  A stereoselective 10-step synthesis of iodophenoxy analogues of (2R,3S)-reboxetine has been developed with the aim of generating a new SPECT imaging agent for the noradrenaline transporter (NAT). In vitro testing of these compounds against various mono-amine transporters showed an ortho-iodophenoxy analogue to have excellent affinity (K-i 8.4 nM) and good selectivity for NAT. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.064
• 作为产物：
  描述：

  肉桂基氯 在 甲基磺酰胺 、 AD-mix-β 、 碳酸氢钠 作用下， 以 水 、 叔丁醇 为溶剂， 反应 96.0h， 以66%的产率得到(2S,3R)-1-chloro-3-phenylpropane-2,3-diol
  参考文献：
  名称：

  Design and synthesis of (2R,3S)-iodoreboxetine analogues for SPECT imaging of the noradrenaline transporter

  摘要：

  A stereoselective 10-step synthesis of iodophenoxy analogues of (2R,3S)-reboxetine has been developed with the aim of generating a new SPECT imaging agent for the noradrenaline transporter (NAT). In vitro testing of these compounds against various mono-amine transporters showed an ortho-iodophenoxy analogue to have excellent affinity (K-i 8.4 nM) and good selectivity for NAT. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.064

文献信息

• Highly stereoselective syn-ring opening of enantiopure epoxides with nitric oxide
  作者：Wentao Wu、Qiang Liu、Yinglin Shen、Rui Li、Longmin Wu

  DOI：10.1016/j.tetlet.2006.12.095

  日期：2007.2

  Reaction of enantiopure epoxides (1) with NO occurred highly stereoselectively, affording syn-ring opened products, nitrates (2). The configuration of 2 was confirmed to be retained by determining the configuration of reduced products 1,2-glycols (4) from 2. A possible mechanism is suggested to trace out the syn-ring opening pathway.

  对映体纯的环氧化物（反应1），没有发生高度立体选择性，得到顺式-环打开产物，硝酸盐（2）。的配置2，确认到通过确定还原产物1,2-二醇（的结构被保留4从）2。提出了一种可能的机制来追踪合成环的开放途径。
• Asymmetric dihydroxylation of primary allylic halides and a concise synthesis of (−)-diepoxybutane
  作者：Koen P.M. Vanhessche、Zhi-Min Wang、K.Barry Sharpless

  DOI：10.1016/s0040-4039(00)73212-6

  日期：1994.5

  Tire asymmetric dihydroxylation (AD) of primary allylic halides is described. Enantiomeric excesses range from 40 to 98%. Subsequent base treatment gives epoxy alcohols in high yields. This strategy is further illustrated by the synthesis of (-)-diepoxybutane, an important C-4-chiral building block.
• Vanhessche Koen P. M., Wang Zhi-Min, Sharpless K. Barry, Tetrahedron Lett, 35 (1994) N 21, S 3469-3472
  作者：Vanhessche Koen P. M., Wang Zhi-Min, Sharpless K. Barry

  DOI：——

  日期：——
• Design and synthesis of (2R,3S)-iodoreboxetine analogues for SPECT imaging of the noradrenaline transporter
  作者：Nicola K. Jobson、Andrew R. Crawford、Deborah Dewar、Sally L. Pimlott、Andrew Sutherland

  DOI：10.1016/j.bmcl.2009.07.064

  日期：2009.9

  A stereoselective 10-step synthesis of iodophenoxy analogues of (2R,3S)-reboxetine has been developed with the aim of generating a new SPECT imaging agent for the noradrenaline transporter (NAT). In vitro testing of these compounds against various mono-amine transporters showed an ortho-iodophenoxy analogue to have excellent affinity (K-i 8.4 nM) and good selectivity for NAT. (C) 2009 Elsevier Ltd. All rights reserved.