Methyl (S)-3-Hydroxy-3-(4-nitrophenyl)propanoate | 135505-17-8

• 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: Methyl (S)-3-Hydroxy-3-(4-nitrophenyl)propanoate
• 英文别名: methyl (S)-3-hydroxy-3-(4-nitrophenyl)propionate；methyl 3-hydroxy-3-(4-nitrophenyl)propanoate；Methyl (3S)-3-hydroxy-3-(4-nitrophenyl)propanoate
• CAS: 135505-17-8
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: OBFIKZLNFXSNNQ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl (3S)-3-(4-nitrophenyl)-3-trimethylsilyloxypropanoate 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 Methyl (S)-3-Hydroxy-3-(4-nitrophenyl)propanoate
  参考文献：
  名称：

  The Mukaiyama Aldol and Mukaiyama–Michael Reactions Promoted by Commercially Available Molecular Sieves

  摘要：

  The Mukaiyama aldol reaction of silyl ketene acetals with aldehydes has been effected by using commercially available 4 angstrom molecular sieves (4 angstrom MS) as a promoter. Various silyl ketene acetals and silyl enol ethers have been shown to be effective nucleophiles for this reaction. For the first time, it has been found that 4 angstrom MS can promote the Mukaiyama Michael addition reactions of silyl ketene acetals to alpha,beta-enones.

  DOI：

  10.3987/com-09-s(s)133

文献信息

• Ni(II)-Catalyzed Enantioselective Synthesis of β-Hydroxy Esters with Carboxylate Assistance
  作者：Na Wang、Hongxin Liu、Hang Gao、Jiafeng Zhou、Longzhangdi Zheng、Juan Li、Hong-Ping Xiao、Xinhua Li、Jun Jiang

  DOI：10.1021/acs.orglett.9b02297

  日期：2019.9.6

  decarboxylative aldol reaction between malonic acid half-oxyesters and various carbonyls with carboxylate assistance was developed, affording structurally diverse β-hydroxy esters with good yields and enantioselectivities under mild conditions. Importantly, the broad substrate scope of this methodology enabled rapid accesses to several natural products and their analogues as exemplified by phenylpropanoid, phaitanthrin

  建立了Ni-恶唑啉配合物催化丙二酸半含氧酸酯和各种羰基在羧酸酯辅助下的不对称脱羧醛醇缩合反应，在温和条件下以良好的收率和对映选择性提供了结构多样的β-羟基酯。重要的是，这种方法的广泛的底物范围使人们能够快速获得几种天然产物及其类似物，例如苯丙烷，类赤霉素B和邻苯二甲酸酯。
• 一种手性β羟基酸酯类化合物的合成方法
  申请人：温州大学

  公开号：CN109734600B

  公开（公告）日：2020-09-15

  本发明公开了一种手性β羟基酸酯类化合物的合成方法，其特征在于，所述方法包含下列步骤：以醛类化合物与丙二酸单烷基酯为原料，在有机溶剂中，金属与手性配体为催化剂的条件下直接充分反应，反应结束后反应液经分离纯化得到所述的高立体选择性的β羟基酸酯类化合物。其有益效果主要体现在：1，操作简单；2，能快速构建高立体选择性的β羟基酸酯骨架结构分子；3，反应收率高，立体选择性好。故本发明具有较高的基础研究意义、工业生产价值和社会经济效益。
• Braun, Manfred; Bauer, Claus, Liebigs Annalen der Chemie, 1991, # 11, p. 1157 - 1164
  作者：Braun, Manfred、Bauer, Claus

  DOI：——

  日期：——
• Dirhodium(II) Tetrakis[N-benzene-fused Phthaloyl-(S)-piperidinonate] as a Chiral Lewis Acid: Catalytic Enantioselective Aldol Reactions of Acetate-derived Silylketene Acetals and Aldehydes
  作者：Shunichi Hashimoto、Takuya Washio、Seiichi Nakamura、Masahiro Anada

  DOI：10.3987/com-05-s(k)25

  日期：——
• The Mukaiyama Aldol and Mukaiyama–Michael Reactions Promoted by Commercially Available Molecular Sieves
  作者：Shunichi Hashimoto、Masahiro Anada、Takuya Washio、Yudai Watanabe

  DOI：10.3987/com-09-s(s)133

  日期：——

  The Mukaiyama aldol reaction of silyl ketene acetals with aldehydes has been effected by using commercially available 4 angstrom molecular sieves (4 angstrom MS) as a promoter. Various silyl ketene acetals and silyl enol ethers have been shown to be effective nucleophiles for this reaction. For the first time, it has been found that 4 angstrom MS can promote the Mukaiyama Michael addition reactions of silyl ketene acetals to alpha,beta-enones.