(+/-)-2-phenyl-1,4-butanediol | 6837-05-4

• 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: (+/-)-2-phenyl-1,4-butanediol
• 英文别名: 2-phenylbutane-1,4-diol；2-phenylbutan-1,4-diol；2-Phenyl-1,4-butandiol；2-Phenyl-butan-diol-(1,4)；2-Phenyl-1,4-butanediol
• CAS: 6837-05-4
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: BVDKYMGISZDCIY-UHFFFAOYSA-N

物化性质

• 熔点：
  70 °C
• 沸点：
  165 °C
• 密度：
  1.100±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：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (+/-)-2-phenyl-1,4-butanediol 在 ReH7(i-Pr3P)2 作用下， 以 苯 为溶剂， 反应 29.0h， 以82%的产率得到4-苯基四氢呋喃-2-酮
  参考文献：
  名称：

  A convenient lactonization of diols to γ- and δ-lactones catalysed by transition metal polyhydrides

  摘要：

  Transition metal polyhydrides-catalyzed oxidative condensation of diols to 5 and 6-ring lactones was studied. The regioselective dehydrogenation of unsymmetrically substituted 1,4-diols gave beta- or gamma-substituted gamma-lactones in high yields. The mechanism of dehydrogenation under neutral and mild conditions was discussed.

  DOI：

  10.1016/0022-328x(92)83257-i
• 作为产物：
  描述：

  亚苯甲基丙二酸二乙酯 在 lithium aluminium tetrahydride 作用下， 以 乙醇 为溶剂， 生成 (+/-)-2-phenyl-1,4-butanediol
  参考文献：
  名称：

  Blau, K.; Voerkel,V.; Willecke, L., Journal fur praktische Chemie (Leipzig 1954), 1986, vol. 328, # 1, p. 29 - 34

  摘要：

  DOI：

文献信息

• Acyclic phenylalkanediols as substrates for the study of enzyme recognition: synthesis of substrates and enzymatic resolution via hydrolysis and transesterification
  作者：Angel Rumbero、Isabel Borreguero、José V. Sinisterra、Andrés R. Alcántara

  DOI：10.1016/s0040-4020(99)00941-2

  日期：1999.12

  diacetates, in both cases catalysed by porcine pancreatic lipase (PPL). The absolute configuration of the optically enriched reaction products was determined by formation of Mosher's esters or by the use of the Benzene Sector and Benzene Chirality Rules as obtained from the Circular Dichroism spectra.

  合成了不同的外消旋或前手性苯基烷烃（l，n）-二醇，并通过两种不同的策略进行拆分：在两种情况下，通过猪胰脂肪酶催化（用乙酸乙烯酯进行酶促酯交换反应或相应的双乙酸酯的酶促水解）（ PPL）。光学富集的反应产物的绝对构型是通过形成Mosher's酯或通过使用从圆二色性光谱获得的苯部门和苯手性规则来确定的。
• Aerobic Lactonization of Diols by Biomimetic Oxidation
  作者：Yoshinori Endo、Jan-E. Bäckvall

  DOI：10.1002/chem.201102168

  日期：2011.11.4

  Coming up for air: Highly efficient aerobic lactonization can be carried out by a biomimetic oxidation system based on coupled redox catalysts (ruthenium catalyst and electron transfer mediators). This system leads to a low‐energy electron transfer from diol to molecular oxygen. Various diols were aerobically oxidized to the corresponding five‐ to nine‐membered lactones in good to high yields under

  空气进入：高效的好氧内酯化反应可以通过基于偶合氧化还原催化剂（钌催化剂和电子传递介体）的仿生氧化系统进行。该系统导致低能电子从二醇转移到分子氧。在温和的反应条件下，各种二醇被好氧氧化成相应的五元至九元内酯（见方案）。
• Biological Evaluation and X-ray Co-crystal Structures of Cyclohexylpyrrolidine Ligands for Trypanothione Reductase, an Enzyme from the Redox Metabolism of Trypanosoma
  作者：Raoul De Gasparo、Elke Brodbeck-Persch、Steve Bryson、Nina B. Hentzen、Marcel Kaiser、Emil F. Pai、R. Luise Krauth-Siegel、François Diederich

  DOI：10.1002/cmdc.201800067

  日期：2018.5.8

  were freely soluble and showed competitive inhibition constants (Ki) against Trypanosoma (T.) brucei TR and T. cruzi TR and in vitro activities (half‐maximal inhibitory concentration, IC50) against these parasites in the low micromolar range, with high selectivity against human glutathione reductase. X‐ray co‐crystal structures confirmed the binding of the ligands to the hydrophobic wall of the “mepacrine

  人类非洲锥虫病，南美锥虫病和各种形式的利什曼病是热带疾病，是由锥虫病家族的寄生虫引起的。这些原生动物具有独特的氧化还原代谢，该代谢基于锥虫硫烷和锥虫硫醇还原酶（TR），使TR成为有前途的药物靶标。我们通过基于结构的设计报告了TR的环己基吡咯烷抑制剂的性能和效能的优化。最好的抑制剂是可自由溶解的，并显示出对锥虫（T.）brucei TR和T. cruzi TR的竞争抑制常数（K i）和体外活性（半数最大抑制浓度，IC 50）在低微摩尔范围内对这些寄生虫具有抗人谷胱甘肽还原酶的高选择性。X射线共晶结构证实了配体与“ mepacrine结合位点”的疏水壁的结合，并且具有面向大活性位点表面的新的可提供溶解度的载体。
• Cp*Ir Complex-Catalyzed <i>N</i>-Heterocyclization of Primary Amines with Diols:  A New Catalytic System for Environmentally Benign Synthesis of Cyclic Amines
  作者：Ken-ichi Fujita、Takeshi Fujii、Ryohei Yamaguchi

  DOI：10.1021/ol048619j

  日期：2004.9.1

  [reaction: see text] A new efficient method for the N-heterocyclization of primary amines with diols catalyzed by a CpIr complex was developed. A variety of five-, six-, and seven-membered cyclic amines were synthesized in good to excellent yields with the formation of only water as a byproduct. A two-step asymmetric synthesis of (S)-2-phenylpiperidine was also achieved using (R)-1-phenylethylamine

  [反应：见正文]开发了一种新的有效方法，用于CpIr配合物催化的伯胺与二醇的N-杂环化。合成了多种五元，六元和七元环状胺，其收率好至极佳，仅形成水作为副产物。使用（R）-1-苯基乙胺作为起始伯胺，还可以实现两步不对称合成（S）-2-苯基哌啶。
• 5-HYDROXYPYRIMIDINE-4-CARBOXAMIDE COMPOUND
  申请人：Kuribayashi Takeshi

  公开号：US20110112103A1

  公开（公告）日：2011-05-12

  The present invention provides compounds which promote erythropoietin production. Compounds represented by the following general formula (1) or pharmacologically acceptable salts thereof are provided: [wherein, R 1 represents a group —X-Q 1 , X-Q 1 -Y-Q 2 or X-Q 1 -Y-Q 2 -Z-Q 3 , X represents a single bond, —CH 2 — or the like, Q 1 represents a monocyclic or bicyclic heterocyclic group which may have substituent(s), Y represents a single bond, —CH 2 —, or the like, Q 2 represents a monocyclic or bicyclic hydrocarbon ring group which may have substituent(s) or a monocyclic or bicyclic heterocyclic group which may have substituent(s), Z represents a single bond, —CR 11 R 12 — or the like, R 11 and R 12 each independently represents a hydrogen atom, a halogen atom or the like, Q 3 represents a phenyl group which may have substituent(s), a C 3 -C 7 cycloalkyl group which may have substituent(s), a C 3 -C 7 cycloalkenyl group which may have substituent(s) or a monocyclic or bicyclic heterocyclic group which may have substituent(s), R 2 represents a C 1 -C 3 alkyl group or the like, and R 3 represents a hydrogen atom or a methyl group].

  本发明提供促进促红细胞生成素产生的化合物。提供以下一般式（1）表示的化合物或其药理学上可接受的盐： [其中，R 1 表示一个基团-X-Q 1 ，X-Q 1 -Y-Q 2 或X-Q 1 -Y-Q 2 -Z-Q 3 ，X表示一个单键，-CH 2 -或类似物，Q 1 表示可能具有取代基的单环或双环杂环基团，Y表示一个单键，-CH 2 -或类似物，Q 2 表示可能具有取代基的单环或双环碳氢环基团或可能具有取代基的单环或双环杂环基团，Z表示一个单键，-CR 11 R 12 -或类似物，R 11 和R 12 各自独立地表示氢原子、卤素原子或类似物，Q 3 表示可能具有取代基的苯基团，可能具有取代基的C 3 -C 7 环烷基团，可能具有取代基的C 3 -C 7 环烯基团或可能具有取代基的单环或双环杂环基团，R 2 表示C 1 -C 3 烷基团或类似物，R 3 表示氢原子或甲基基团]。