1,2-苯二甲酸单(1-甲基-2-丙炔基)酯 | 42969-62-0

• 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: 1,2-苯二甲酸单(1-甲基-2-丙炔基)酯
• 英文名称: (+/-)-but-3'-yn-2'-yl hydrogen phthalate
• 英文别名: (+/-)-3-butyn-2-ol hydrogen phthalate；1-butyn-3-ol hydrogen phthalate；opt.-akt. Butin-(3)-ol-(2)-hydrogenphthalat；Butin-(3)-ol-(2)-hydrogenphthalat；2-But-3-yn-2-yloxycarbonylbenzoic acid
• CAS: 42969-62-0
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: POOBVOATKBYZQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-苯二甲酸单(1-甲基-2-丙炔基)酯 生成 (R)-(+)-3-丁炔-2-醇
  参考文献：
  名称：

  Grattan, T. J.; Whitehurst, J. S., Journal of the Chemical Society. Perkin transactions I, 1990, # 1, p. 11 - 18

  摘要：

  DOI：
• 作为产物：
  描述：

  苯酐 、 3-丁炔-2-醇 在 sodium hydroxide 作用下， 反应 0.08h， 以73%的产率得到1,2-苯二甲酸单(1-甲基-2-丙炔基)酯
  参考文献：
  名称：

  烯丙胺的立体异构体，作为B型单胺氧化酶的灭活剂。活性部位的立体化学探针。

  摘要：

  已详细研究了一系列18种叔α-烯丙胺立体异构体对线粒体单胺氧化酶B型（MAO-B）的灭活动力学。发现N-甲基-N-芳烷基戊2,3-二烯胺中丙二烯基的手性对失活速率有深远影响，（R）-丙二烯的效价比其（ S）-allenic同行。N-苯乙基或N-α-取代的芳烷基取代基的存在严重损害了（S）-烯烯使MAO失活的能力。（R，R）-和（S，S）-N-甲基-N-（1,2,3,4-四氢-1-萘基）-penta-2的烯丙基和芳烷基中的相反手性， 3-二烯胺+ ++导致灭活速率的差异超过3个数量级。用一系列可逆的芳烷基胺抑制剂进一步检查了MAO-B的立体选择性。因此，确定（R）-1,2,3,4-四氢-1-萘胺的效价是其对映体的150倍。

  DOI：

  10.1021/jm00403a012

文献信息

• Stereoisomers of allenic amines as inactivators of monoamine oxidase type B. Stereochemical probes of the active site
  作者：Roger A. Smith、Robert L. White、Allen Krantz

  DOI：10.1021/jm00403a012

  日期：1988.8

  The kinetics of inactivation of mitochondrial monoamine oxidase type B (MAO-B) by a series of 18 stereoisomers of tertiary alpha-allenic amines have been investigated in detail. The chirality of the allene group in N-methyl-N-aralkylpenta-2,3-dienamines was found to have a profound effect on the inactivation rate, with the (R)-allenes being up to 200-fold more potent than their (S)-allenic counterparts

  已详细研究了一系列18种叔α-烯丙胺立体异构体对线粒体单胺氧化酶B型（MAO-B）的灭活动力学。发现N-甲基-N-芳烷基戊2,3-二烯胺中丙二烯基的手性对失活速率有深远影响，（R）-丙二烯的效价比其（ S）-allenic同行。N-苯乙基或N-α-取代的芳烷基取代基的存在严重损害了（S）-烯烯使MAO失活的能力。（R，R）-和（S，S）-N-甲基-N-（1,2,3,4-四氢-1-萘基）-penta-2的烯丙基和芳烷基中的相反手性， 3-二烯胺+ ++导致灭活速率的差异超过3个数量级。用一系列可逆的芳烷基胺抑制剂进一步检查了MAO-B的立体选择性。因此，确定（R）-1,2,3,4-四氢-1-萘胺的效价是其对映体的150倍。
• Electrical and mechanical anharmonicities from NIR-VCD spectra of compounds exhibiting axial and planar chirality: The cases of (S)-2,3-pentadiene and methyl-d3 (R)- and (S)-[2.2]paracyclophane-4-carboxylate
  作者：Sergio Abbate、Giovanna Longhi、Fabrizio Gangemi、Roberto Gangemi、Stefano Superchi、Anna Maria Caporusso、Renzo Ruzziconi

  DOI：10.1002/chir.21013

  日期：2011.10

  The IR and Near infrared (NIR) vibrational circular dichroism (VCD) spectra of molecules endowed with noncentral chirality have been investigated. Data for fundamental, first, and second overtone regions of (S)‐2,3‐pentadiene, exhibiting axial chirality, and methyl‐d3 (R)‐ and (S)‐[2.2]paracyclophane‐4‐carboxylate, exhibiting planar chirality have been measured and analyzed. The analysis of NIR and

  研究了具有非中心手性的分子的IR和近红外（NIR）振动圆二色性（VCD）光谱。（S）-2,3-戊二烯的基本，第一和第二个泛音区域的数据，表现出轴向手性，以及甲基d 3（R）-和（S）[2.2]对环烷-4-羧酸酯，具有平面手性，已经过测量和分析。NIR和IR VCD光谱的分析基于本地模式模型和密度泛函理论（DFT）的使用，为所有CH键提供了机械和电气非谐项。实验光谱和计算光谱的比较是令人满意的，并且可以监测分子中不对称电荷分布的细节：这些细节包括谐波频率，主要非谐常数，原子极和轴向张量以及它们的关于CH拉伸坐标的一阶和二阶导数。手性，2011年。©2011 Wiley©Liss，Inc.
• Amide, urea, and carbamate analogs of the muscarinic agent [4-[[N-(3-chlorophenyl)carbamoyl]oxy]-2-butynyl]trimethylammonium chloride
  作者：Bjoern M. Nilsson、Hugo M. Vargas、Uli Hacksell

  DOI：10.1021/jm00093a011

  日期：1992.7

  A series of amide, urea, and carbamate analogues of the muscarinic (M1) ganglionic stimulant [4-[[N-(3-chlorophenyl)carbamoyl]oxy]-2-butynyl]trimethylammonium chloride (McN-A-343; 1) was prepared. The C1-methyl-substituted carbamates 8-11 were resolved into the enantiomers. In order to investigate the ganglionic stimulant activity and affinity of the new compounds we studied their ability to increase mean arterial blood pressure (MAP) in the pithed rat and their ability to displace the M1 receptor selective antagonist [H-3]pirenzepine from rabbit sympathetic ganglia. The quaternary ammonium derivatives of 1, but not their corresponding tertiary amines, displayed ganglionic stimulant properties. The urea derivative 14 and the acetamide derivative 18 were almost equipotent to 1 as ganglionic agonists. In addition, 14 and 18 showed only 2- to 3-fold less affinity to ganglionic muscarinic receptors than 1. Introduction of a methyl group in the 1 position of the butynyl chain of 1 and its 4-chlorophenyl analogue increased ganglionic stimulant potency. The resulting (+/-)-9 and (+/-)-11 were the most potent analogues in this study. They were found to be partial agonists and showed 5- and 16-fold higher potency than 1, respectively, in increasing the MAP. They also displayed 6- and 18-fold higher affinity than 1 for ganglionic M1 receptors. The (S)-enantiomers of 9 and 11 were 1.5- and 4.9-fold more potent, respectively, than their antipodes as ganglionic muscarinic stimulants. The C1-methyl-substituted urea and acetamide derivatives (15 and 19) were 1.5- and 3-fold less potent than 1 and displayed several-fold lower affinity for ganglionic M1 receptors. The new quaternary analogues retained the selectivity for ganglionic muscarinic receptors since they produced weak partial agonist effects on the guinea pig ileum and showed several-fold lower nicotinic activity than 1 in the frog rectus abdominis assay.
• Cotterill, Ann S.; Gill, Melvyn; Gimenez, Alberto, Journal of the Chemical Society. Perkin transactions I, 1994, # 22, p. 3269 - 3276
  作者：Cotterill, Ann S.、Gill, Melvyn、Gimenez, Alberto、Milanovic Nives M.

  DOI：——

  日期：——
• SMITH, ROGER A.;WHITE, ROBERT L.;KRANTZ, ALLEN, J. MED. CHEM., 31,(1988) N 8, C. 1558-1566
  作者：SMITH, ROGER A.、WHITE, ROBERT L.、KRANTZ, ALLEN

  DOI：——

  日期：——