(S)-1-(3-硝基苯基)丙醇 | 188770-83-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-1-(3-硝基苯基)丙醇
• 中文别名: (S)1-(3-硝基苯基)丙醇
• 英文名称: (S)-1-(3-nitrophenyl)propan-1-ol
• 英文别名: 1-(3-nitrophenyl)-1-propanol；(S)-1-(3-nitrophenyl)propanol；(1S)-1-(3-nitrophenyl)propan-1-ol
• CAS: 188770-83-4
• 化学式: C₉H₁₁NO₃
• mdl: MFCD08064293
• 分子量: 181.191
• InChiKey: LSEJDXFJBNGGBI-VIFPVBQESA-N

物化性质

• 沸点：
  295.3±23.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(3-硝基苯基)丙醇 在 sodium ethanolate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 2-[(S)-1-(3-Nitro-phenyl)-propyl]-malonic acid diethyl ester
  参考文献：
  名称：

  A Convergent, Scalable Synthesis of HIV Protease Inhibitor PNU-140690

  摘要：

  PNU-140690, an inhibitor of the HIV protease enzyme undergoing clinical evalution as a chemotherapeutic agent for treatment of AIDS, was synthesized by a convergent approach amenable to large-scale preparation in a pilot plant environment. The key step is the aldol addition of nitroaromatic ester (+)-8 to aldehyde 19e. The two stereocenters present in the target molecule were each set independently by resolution of enantiomers. Intermediates along the synthetic routes were chosen to maximize opportunities for isolation and purification by crystallization.

  DOI：

  10.1021/jo9809229
• 作为产物：
  描述：

  α-ethyl-3-nitro-benzenemethanol 生成 (S)-1-(3-硝基苯基)丙醇
  参考文献：
  名称：

  J. Org. Chem. 1998, 63, 7348-7356

  摘要：

  DOI：

文献信息

• Cobalt(ii)-catalyzed asymmetric hydrosilylation of simple ketones using dipyridylphosphine ligands in air
  作者：Feng Yu、Xi-Chang Zhang、Fei-Fei Wu、Ji-Ning Zhou、Wenjun Fang、Jing Wu、Albert S. C. Chan

  DOI：10.1039/c1ob05494e

  日期：——

  In the presence of PhSiH3 as the hydride donor, catalytic amounts of non-racemic dipyridylphosphine and an easy-to-handle cobalt salt Co(OAc)2·4H2O formed in situ an effective catalyst system for the asymmetric reduction of a diverse range of aryl alkyl ketones with moderate-to-excellent enantioselectivities (up to 96% ee). This approach tolerated the handling of both catalyst and reactants under air without special precautions.

  在存在作为氢供体的PhSiH3的情况下，非消旋的二吡啶膦和易于操作的钴盐Co(OAc)2·4H2O现场形成有效的催化系统，用于多种芳基烷基酮的对映选择性还原，其对映选择性从中等到优秀（最高可达96% ee）。这种方法在空气中处理催化剂和反应物时不需要特别预防措施。
• Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by titanium-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-bi-2-naphthol complex
  作者：Fu-Yao Zhang、Albert S.C. Chan

  DOI：10.1016/s0957-4166(97)00501-6

  日期：1997.11

  The use of Ti(H8-BINOL) (H8-BINOL=5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-bi-2-naphthol) as a catalyst for the diethylzinc addition to aldehydes has been studied, and high e.e.s (up to 98.5%) were obtained for the chiral alcohol products. The results were significantly better than those obtained with the corresponding Ti(BINOL) catalyst (BINOL=1,1′-bi-2-naphthol).

  Ti（H 8 -BINOL）（H 8 -BINOL = 5,5'，6,6'，7,7'，8,8'-八氢-1,1'-bi-2-萘酚）的用途已经研究了用于将二乙基锌加成醛的催化剂，并且对于手性醇产物获得了高ee（高达98.5％）。结果明显好于用相应的Ti（BINOL）催化剂（BINOL = 1,1'-bi-2-萘酚）获得的结果。
• Process to produce a protease inhibitor
  申请人：Pharmacia & Upjohn Company

  公开号：US06077963A1

  公开（公告）日：2000-06-20

  Disclosed is a novel process and novel intermediates to prepare [R-(R*,R*)]-N-[3-[1-[5,6-dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propy l-2H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide (XIX) ##STR1## which is a protease inhibitor useful in treating humans infected with the HIV virus.

  揭示了一种新颖的过程和新颖的中间体，用于制备[R-(R*，R*)]-N-[3-[1-[5,6-二氢-4-羟基-2-氧代-6-(2-苯乙基)-6-丙基-2H-吡喃-3-基]丙基]苯基]-5-(三氟甲基)-2-吡啶磺酰胺（XIX），该化合物是一种蛋白酶抑制剂，用于治疗感染HIV病毒的人类。
• Synthesis of Novel 1,4-Bissulfonamide Ligands for Enantioselective Addition of Diethylzinc to Aldehydes
  作者：Minghua Yang、Jiangtao Sun、Chengjian Zhu

  DOI：10.1002/cjoc.201180303

  日期：2011.8

  Several novel chiral sulfonamide ligands based on (1R,2S,4R,5S)‐1,4‐diamino‐2,5‐dimethylcyclohexane skeleton have been synthesized and their application in the enantioselective addition of diethylzinc to aldehydes was investigated in the presence of Ti(OiPr)4. The effect of ligands, temperature and the loading amount of ligands was studied. Under optimized conditions, enantioselective addition of diethylzinc

  合成了几种基于（1 R，2 S，4 R，5 S）-1,4-二氨基-2,5-二甲基环己烷骨架的新型手性磺酰胺配体，并研究了它们在二乙基锌对醛的对映选择性加成中的应用。 Ti（O i Pr）4的存在。研究了配体的影响，温度和配体的负载量。在最佳条件下，二乙基锌与各种芳基醛和脂族醛的对映选择性加成反应顺利进行，并提供了高达88％ee的手性仲醇。
• Supramolecular Interlocked Biphenyl Ligands for Enantioselective Ti-Catalyzed Alkylation of Aromatic Aldehydes
  作者：Jan Felix Scholtes、Oliver Trapp

  DOI：10.1021/acs.organomet.9b00262

  日期：2019.10.28

  (S)-amino-acid-derived interaction sites in the 5,5′-position results in a spontaneous desymmetrization. This process is driven by well-defined intermolecular hydrogen bonding, which leads to diastereoselective interlocking of the interaction sites of two biphenol units. The axial chirality of the subunits within the supramolecular dimer is dictated by the chiral information in the interacting selector units. The

  的取代的Tropos 2,2'-双酚与（S）中以自发desymmetrization的5,5'-位置导致氨基酸衍生相互作用位点。这个过程是由明确定义的分子间氢键驱动的，这导致两个双酚单元相互作用位点的非对映选择性互锁。超分子二聚体中亚基的轴向手性由相互作用的选择器单元中的手性信息决定。通过核磁共振波谱，X射线晶体学和氢-氘交换研究了该复合物的结构。配体已成功用于Ti介导的芳族醛的不对称烷基化。