2-(<1,1'-biphenyl>-4-ylmethyl)-1,3-propanediol | 152961-72-3

• 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-(<1,1'-biphenyl>-4-ylmethyl)-1,3-propanediol
• 英文别名: 2-<(4-Phenylphenyl)methyl>propane-1,3-diol；2-[(4-Phenylphenyl)methyl]propane-1,3-diol
• CAS: 152961-72-3
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: PCKFGBPVDIODCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-(<1,1'-biphenyl>-4-ylmethyl)-1,3-propanediol 在 吡啶 、 2,6-二叔丁基-4-甲基苯酚 作用下， 以 二氯甲烷 、 异丙醚 、 水 、 二甲基亚砜 为溶剂， 反应 47.0h， 生成 (R)-3-Cyano-2-<(4-phenylphenyl)methyl>propyl acetate
  参考文献：
  名称：

  An efficient enantioselective total synthesis of antitumor lignans: synthesis of enantiomerically pure 4-hydroxyalkanenitriles via an enzymic reaction

  摘要：

  Efficient preparation of optically pure 4-hydroxyalkanenitriles, la-f, was achieved via an enzymatic reaction using lipase PS (Pseudomonas sp.). Optically pure (R)-4-hydroxy-3-[[3,4-(methylenedioxy)phenyl]methyl]butanenitrile (1a) was applied to the enantioselective synthesis of three types of antitumor lignans, (-)-hinokinin, (-)-isodeoxypodophyllotoxin, and (+)-isostegane.

  DOI：

  10.1021/jo00073a034
• 作为产物：
  描述：

  dimethyl 2-(<1,1'-biphenyl>-4-ylmethylene)-1,3-propanedioate 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 48.0h， 生成 2-(<1,1'-biphenyl>-4-ylmethyl)-1,3-propanediol
  参考文献：
  名称：

  锰钳配合物催化无受体脱氢偶联反应发散合成吡唑

  摘要：

  使用醇作为碳源的分子定义的 Mn(I) 配合物催化的无受体脱氢偶联 (ADC) 反应能够合成多取代的吡唑。对称吡唑是通过 1,3-二醇与肼偶联制备的。不对称取代的吡唑是利用伯醇与腙的 ADC 反应生成的。

  DOI：

  10.1002/chem.202401105

文献信息

• Dicarboxylic Acid Dipeptide Neutral Endopeptidase Inhibitors
  作者：Gary M. Ksander、Raj D. Ghai、Reynalda deJesus、Clive Diefenbacher、Andrew Yuan、Carol Berry、Yumi Sakane、Angelo Trapani

  DOI：10.1021/jm00010a014

  日期：1995.5

  The synthesis of three series of dicarboxylic acid dipeptide neutral endopeptidase 24.11 (NEP) inhibitors is described. In particular, the amino butyramide 21a exhibited potent NEP inhibitory activity (IC50 = 5.0 nM) in vitro and in vivo. Blood levels of 21a were determined using an ex vivo method by measuring plasma inhibitory activity in conscious rats, mongrel dogs, and cynomolgus monkeys. Free drug concentrations were 10-1500 times greater than the inhibitory constant for NEP over the course of a 6 h experiment. A good correlation of free drug concentrations was obtained when comparing values determined by the ex vivo analysis to those calculated from direct HPLC measurements. Plasma atrial natriuretic factor (exogenous) levels were elevated in rats and dogs after oral administration of 19a. Urinary volume and urinary sodium excretion were also potentiated in anesthetized dogs treated with 21a.
• An efficient enantioselective total synthesis of antitumor lignans: synthesis of enantiomerically pure 4-hydroxyalkanenitriles via an enzymic reaction
  作者：Toshiyuki Itoh、Junichi Chika、Yumiko Takagi、Shigenori Nishiyama

  DOI：10.1021/jo00073a034

  日期：1993.10

  Efficient preparation of optically pure 4-hydroxyalkanenitriles, la-f, was achieved via an enzymatic reaction using lipase PS (Pseudomonas sp.). Optically pure (R)-4-hydroxy-3-[[3,4-(methylenedioxy)phenyl]methyl]butanenitrile (1a) was applied to the enantioselective synthesis of three types of antitumor lignans, (-)-hinokinin, (-)-isodeoxypodophyllotoxin, and (+)-isostegane.
• Divergent Synthesis of Pyrazoles via Manganese Pincer Complex Catalyzed Acceptorless Dehydrogenative Coupling Reactions
  作者：Koushik Sarkar、Pramod Kumar、Arjun Mule、Biplab Maji

  DOI：10.1002/chem.202401105

  日期：——

  defined Mn(I)-complex catalyzed acceptorless dehydrogenative coupling (ADC) reactions employing alcohols as the carbon source enabled the synthesis of multi-substituted pyrazoles. Symmetrical pyrazoles were made via the coupling of 1,3-diols with hydrazines. The unsymmetrically substituted pyrazoles were created using the ADC reaction of primary alcohols with hydrazones.

  使用醇作为碳源的分子定义的 Mn(I) 配合物催化的无受体脱氢偶联 (ADC) 反应能够合成多取代的吡唑。对称吡唑是通过 1,3-二醇与肼偶联制备的。不对称取代的吡唑是利用伯醇与腙的 ADC 反应生成的。