(2S,3S)-2-nitro-5-phenyl-1,3-pentanediol

• 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,3S)-2-nitro-5-phenyl-1,3-pentanediol
• 英文别名: 1,2,4-trideoxy-4-nitro-1-phenyl-L-threopentitol；(2S,3S)-2-nitro-5-phenylpentan-1,3-diol；(2S,3S)-2-nitro-5-phenylpentane-1,3-diol
• 化学式: C₁₁H₁₅NO₄
• 分子量: 225.244
• InChiKey: GXCUFYWSSIMQLZ-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯丙醛 、 2-硝基乙醇 在 trilithium tris[(R)-1,1'-bi(2-naphtholato)]lanthanate 作用下， 以 四氢呋喃 为溶剂， 反应 90.5h， 以50%的产率得到(2S,3S)-2-nitro-5-phenyl-1,3-pentanediol
  参考文献：
  名称：

  CATALYTIC ASYMMETRIC SYNTHESIS OF NITROALDOLS USING A LANTHANUM-LITHIUM-BINOL COMPLEX: (2S,3S)-2-NITRO-5-PHENYL-1,3-PENTANEDIOL

  摘要：

  DOI：

  10.15227/orgsyn.078.0014

文献信息

• Diastereoselective and Highly Enantioselective Henry Reactions using C1-Symmetrical Copper(II) Complexes
  作者：Antoinette Chougnet、Guoqi Zhang、Kegang Liu、Daniel Häussinger、Andreas Kägi、Thomas Allmendinger、Wolf-D. Woggon

  DOI：10.1002/adsc.201100157

  日期：2011.7

  Catalytic Henry reactions of aliphatic aldehydes and prochiral nitro compounds were investigated using copper(II) complexes of 14 C1‐symmetrical ligands derived from (1R,2R)(−)‐diaminocyclohexane. β‐Nitro alcohols with syn:anti ratios of up to 5.7 and excellent ee values for both diastereosimers were obtained.

  使用衍生自（1 R，2 R）（-）-二氨基环己烷的14 C 1对称配体的铜（II）配合物研究了脂肪醛和前手性硝基化合物的催化亨利反应。β硝基醇与顺式：反向上的比率5.7和优异的ee值获得两个diastereosimers值。
• Efficient Diastereoselective and Enantioselective Nitroaldol Reactions from Prochiral Starting Materials: Utilization of La-Li-6,6'-Disubstituted BINOL Complexes as Asymmetric Catalysts
  作者：Hiroaki Sasai、Teruhisa Tokunaga、Shizue Watanabe、Takeyuki Suzuki、Noriie Itoh、Masakatsu Shibasaki

  DOI：10.1021/jo00128a005

  日期：1995.11
• Asymmetric nitroaldol reaction catalyzed by copper–diamine complexes: selective construction of two contiguous stereogenic centers
  作者：Rafał Kowalczyk、Jacek Skarżewski

  DOI：10.1016/j.tetasy.2009.10.001

  日期：2009.11

  Chiral copper(II) complexes of secondary bisamines derived from 1,2-diaminocyclohexane were successfully used in the diastereoselective nitroaldol reaction. The reactions were carried out in the presence of 10 mol % of the Cu(II) complex and 7.7 mol % of i-Pr2NEt in 2-propanol at -30 degrees C. Good to excellent yields, enantioselectivities of up to 99%, and moderate to excellent diastereoselectivities were obtained for both aromatic or aliphatic aldehydes and various prochiral nitrocompounds forming the corresponding beta-nitroalcohols with two contiguous stereocenters. (C) 2009 Elsevier Ltd. All rights reserved.
• CATALYTIC ASYMMETRIC SYNTHESIS OF NITROALDOLS USING A LANTHANUM-LITHIUM-BINOL COMPLEX: (2S,3S)-2-NITRO-5-PHENYL-1,3-PENTANEDIOL
  作者：Sasai, Hiroaki、Watanabe, Shizue、Suzuki, Takeyuki、Shibasaki, Masakatsu、Havas, Fabien、Magomedov, Nabi A.、Hart, David J.

  DOI：10.15227/orgsyn.078.0014

  日期：——