iso-propyl 3-hydroxybutyrate | 87128-49-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: iso-propyl 3-hydroxybutyrate
• 英文别名: (R)-isopropyl 3-hydroxybutanoate；Butanoic acid, 3-hydroxy-, 1-methylethyl ester, (R)-；propan-2-yl (3R)-3-hydroxybutanoate
• CAS: 87128-49-2
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: OHQCTLBHQBPXLU-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  iso-propyl 3-hydroxybutyrate 、 methyl (NZ)-N-[(E)-3-phenylsulfanylprop-2-enylidene]carbamate 生成 (E)-(R)-2-((R)-1-Hydroxy-ethyl)-3-methoxycarbonylamino-5-phenylsulfanyl-pent-4-enoic acid isopropyl ester
  参考文献：
  名称：

  HATANAKA, MINORU;PARK, OEE-SOOK;UEDA, IKUO, TETRAHEDRON LETT., 31,(1990) N2, C. 7631-7632

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰乙酸异丙酯 在 Ru[(2,2'-di(PPh₂)-6,6'-di(PO₃H₂)-1,1'-binaphthyl](DMF)2Cl₂ 氢气 、 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、10.34 MPa 条件下， 反应 22.0h， 生成 iso-propyl 3-hydroxybutyrate
  参考文献：
  名称：

  Highly enantioselective catalytic asymmetric hydrogenation of β-keto esters in room temperature ionic liquids

  摘要：

  极性磷酸衍生的Ru-BINAP体系用于在常温离子液体（RTILs）中催化β-酮酯的不对称氢化，获得了完全转化率和比在甲醇中均相反应得到的更高的ee值（高达99.3%），并通过简单提取回收，循环使用了四次，未损失活性和选择性。

  DOI：

  10.1039/b302637j

文献信息

• [EN] BENZIMIDAZOLE DERIVATIVES AS BROMODOMAIN INHIBITORS<br/>[FR] DÉRIVÉS DE BENZIMIDAZOLE COMME INHIBITEURS DES BROMODOMAINES
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2016146738A1

  公开（公告）日：2016-09-22

  Compounds of formula (I) and salts thereof: wherein R1, R2, R3, R4 are defined herein. Compounds of formula (I) and salts thereof have been found to inhibit the binding of the BET family of bromodomain proteins to, for example, acetylated lysine residues and thus may have use in therapy, for example in the treatment of autoimmune and inflammatory diseases, such as rheumatoid arthritis; and cancers.

  式（I）的化合物及其盐：其中R1、R2、R3、R4在此处定义。已发现式（I）的化合物及其盐能够抑制BET家族的溴结构域蛋白与例如乙酰化赖氨酸残基的结合，因此可能在治疗中发挥作用，例如在治疗自身免疫和炎症性疾病（如类风湿性关节炎）和癌症方面。
• Highly enantioselective Ru-catalyzed hydrogenation of β-keto esters using electron-donating bis(trialkylphosphine) ligand-TangPhos
  作者：Chun-Jiang Wang、Haiyan Tao、Xumu Zhang

  DOI：10.1016/j.tetlet.2006.01.093

  日期：2006.3

  Highly electron-donating bis(trialkylphosphine) TangPhos and its corresponding ruthenium complexes provided high enantioselectivities for the hydrogenation of β-keto esters. Up to 99.8% and 99.5% ee have been achieved in hydrogenation of β-alkyl and β-aryl substituted β-keto esters, respectively. Asymmetric hydrogenation of ethyl 4-chloro acetoacetate in 98.2% ee is also reported.

  高度供电子的双（三烷基膦）TangPhos及其相应的钌配合物为β-酮酸酯的氢化提供了高对映选择性。在β-烷基和β-芳基取代的β-酮酯的氢化中，分别获得了高达99.8％和99.5％的ee。还报道了4-氯乙酰乙酸乙酯在98.2％ee中的不对称氢化。
• Asymmetric hydrogenation by RuCl₂(R-Binap)(dmf)_n encapsulated in silica-based nanoreactors
  作者：Juan Peng、Xuefeng Wang、Xiaoming Zhang、Shiyang Bai、Yaopeng Zhao、Can Li、Qihua Yang

  DOI：10.1039/c4cy00228h

  日期：——

  RuCl₂-(R-Binap)(dmf)_n encapsulated in silica-based nanoreactors: a solid catalyst as a whole, but a homogeneous catalyst on the nanoscale.

  RuCl₂-(R-Binap)(dmf)_n被封装在基于硅的纳米反应器中：作为一个固体催化剂，但在纳米尺度上是一个均相催化剂。
• Stereochemical Investigation on Asymmetrically Modified Raney Nickel Catalyst. Mode of Interaction between Modifying Reagent and Substrate in the Enantioface-differentiating Process
  作者：Akira Tai、Tadao Harada、Yuji Hiraki、Sigeki Murakami

  DOI：10.1246/bcsj.56.1414

  日期：1983.5

  The mode of enantioface-differentiating hydrogenation with asymmetrically modified Raney nickel (MRNi) was investigated by using various sorts of modifying reagents and substrates. The optical yields (O.Y.) of the hydrogenation of methyl acetoacetate over MRNi for different modifying reagents occured in the following order: (Remark: Graphics omitted.), (Remark: Graphics omitted.). The hydrogenation

  通过使用各种改性试剂和底物研究了不对称改性阮内镍（MRNi）的对映面差异化氢化模式。对于不同的改性剂，乙酰乙酸甲酯在 MRNi 上氢化的光学产率 (OY) 按以下顺序发生：（备注：省略图形。），（备注：省略图形。）。结构的各种底物（备注：图形省略。），在酒石酸改性的雷尼镍（TA-MRNi）上的氢化，只有当取代基 -Y 像羰基一样作为良好的氢键受体时才会产生高光学产率基团，底物与酒石酸的两个羟基之间有两对氢键。至于在这种情况下反应的立体化学，（R，R)-TA-MRNi 总是产生过量的 (R)-产物。基于反应的立体化学和修饰试剂与底物之间氢键的作用，提出了一种立体化学模型来洗脱...
• Chirally functionalized mesoporous organosilicas with built-in BINAP ligand for asymmetric catalysis
  作者：Peiyuan Wang、Xiao Liu、Jie Yang、Yan Yang、Lei Zhang、Qihua Yang、Can Li

  DOI：10.1039/b913808k

  日期：——

  The chirally functionalized periodic mesoporous organosilica (PMO) with C2-symmetric chiral building blocks, BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl), in the pore wall was successfully synthesized for the first time using a successive co-condensation and post-synthesis modification method. Chiral BINAPO (2,2′-bis(diphenylphosphinooxide)-1,1′-binaphthyl) bridging mesoporous organosilica with highly ordered 2-D hexagonal structure was first synthesized by co-condensation of (R)-5,5′-bis(3-triethoxysilylpropyl-1-ureyl)-2,2′-bis(diphenylphosphinooxide)-1,1′-binaphthy with tetramethoxylsilane in the presence of block copolymer P123 as template under weakly acidic conditions. The BINAPO in the pore wall of PMO was reduced with trichlorosilane to generate BINAP using a post-synthesis modification method. The chiral PMO with built-in BINAP (coordination with [RuCl2-(benzene)]2) is an efficient solid catalyst for the asymmetric hydrogenation of β-keto esters with ee as high as 99%, which is among the highest ever reported for the chirally functionalized PMOs in asymmetric catalysis.

  首次成功合成了孔壁中具有C2对称性手性构筑单元BINAP（2,2′-双(二苯基膦)-1,1′-联萘）的手性官能化周期性介孔有机硅（PMO），采用连续共缩聚和后合成修饰方法。通过在弱酸性条件下以嵌段共聚物P123为模板，首次通过（R）-5,5′-双(3-三乙氧基硅丙基-1-脲基)-2,2′-双(二苯基膦氧)-1,1′-联萘与四甲氧基硅烷的共缩聚合成了具有高度有序的二维六方结构的BINAPO（2,2′-双(二苯基膦氧)-1,1′-联萘）桥连介孔有机硅。通过后合成修饰方法，使用三氯硅烷将PMO孔壁中的BINAPO还原生成BINAP。内置BINAP（与[RuCl2-(苯)]2配位）的手性PMO是一种高效的固体催化剂，用于β-酮酯的不对称氢化，其ee值高达99%，这是不对称催化中手性官能化PMO报道的最高值之一。