(S)-(-)-α-methyltropic acid | 59492-59-0

• 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: (S)-(-)-α-methyltropic acid
• 英文别名: (2S)-3-hydroxy-2-methyl-2-phenylpropanoic acid
• CAS: 59492-59-0
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: ISSYFABJJSOCQG-SNVBAGLBSA-N

物化性质

• 熔点：
  85.5-86.5 °C
• 沸点：
  330.8±30.0 °C(Predicted)
• 密度：
  1.215±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-α-methyltropic acid 在 吡啶 作用下， 以 异丙醇 为溶剂， 反应 11.0h， 生成 (-)-2-(diethylamino)ethyl 2-methyl-2-phenyl-3-(tosyloxy)propanoate
  参考文献：
  名称：

  Molecular modification of anticholinergics as probes for muscarinic receptors. 2. Amino esters of .alpha.-methyltropic acid

  摘要：

  As a continuation of our goals to study molecular probes for muscarinic cholinergic receptors, a series of 3-substituted 2-methyl-2-phenylpropanoates with the general structure of C6H5C(CH2X)(CH3)COOCH2CH2NEt2 where X = OH, OTs, F, Cl, Br, I, and OAc were prepared and their antispasmodic activities examined on isolated rat ileum preparations. Structure-activity relationship studies with these compounds provide further evidence suggesting that binding of an aromatic moiety in a specific location within the hydrophobic region of the receptor is important for anticholinergic potency. A nucleophilic displacement of chloride by "naked" fluoride under mild conditions is also reported.

  DOI：

  10.1021/jm00385a028
• 作为产物：
  描述：

  2-甲基-2-苯基-1,3-丙烷二醇 在 Jones reagent 、 2,6-bis((S)-3,3-dibutyl-2-phenyl-3,4-dihydro-2H-pyrrol-5-yl)pyridine 、 水 、 sodium hydroxide 、 copper dichloride 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 5.5h， 生成 (S)-(-)-α-methyltropic acid
  参考文献：
  名称：

  Asymmetric Synthesis of All-Carbon Quaternary Stereocenters via Desymmetrization of 2,2-Disubstituted 1,3-Propanediols

  摘要：

  DOI：

  10.1021/ja1103102

文献信息

• Easy Access to Esters with a Benzylic Quaternary Carbon Center from Diallyl Malonates by Palladium-Catalyzed Decarboxylative Allylation
  作者：Daisuke Imao、Akihiro Itoi、Asako Yamazaki、Masamichi Shirakura、Ryota Ohtoshi、Kenta Ogata、Yohki Ohmori、Tetsuo Ohta、Yoshihiko Ito

  DOI：10.1021/jo0621569

  日期：2007.3.1

  used did not affect the catalytic cycle. Catalysis in [bmim][BF4], a well-known ionic liquid, was inhibited as a result of formation of a hydrogen bond between a carboxylate anion and a [bmim]+ cation; however, the reaction in [bdmim][BF4], in which the acidic proton of [bmim][BF4] was replaced with a methyl group, proceeded smoothly. The catalytic mechanism was investigated using a tetradeuterated

  在温和条件下，2-烷基-2-芳基丙二酸二烯丙基酯迅速经历了钯催化的脱羧烯丙基化。相反，在相同条件下，没有与烯丙基2，2-二烷基丙二酸酯发生反应。发现给电子的膦配体对于该反应是至关重要的。所使用的大多数溶剂不影响催化循环。由于在羧酸根阴离子和[bmim] +阳离子之间形成氢键，因此抑制了在众所周知的离子液体[bmim] [BF 4 ]中的催化。但是，在[bdmim] [BF 4 ]中的反应，其中[bmim] [BF 4用甲基取代]，进行顺利。使用四氘代底物和酶促合成的对映体富集的2-甲基-2-苯基丙二酸甲基烯丙酯，研究了催化机理。发现甚至缺乏电子的亚磷酸酯配体对于催化烯丙基2-甲基-2-（2-或4-硝基苯基）丙二酸酯也具有活性。
• Nickel-catalyzed enantioselective hydrovinylation of silyl-protected allylic alcohols: An efficient access to homoallylic alcohols with a chiral quaternary center
  作者：Qi Zhang、Shou-Fei Zhu、Yan Cai、Li-Xin Wang、Qi-Lin Zhou

  DOI：10.1007/s11426-010-4036-6

  日期：2010.9

  Asymmetric hydrovinylation of silyl-protected allylic alcohols catalyzed by nickel complexes of chiral spiro phosphoramidite ligands was developed. A series of homoallylic alcohols with a chiral quaternary center were produced in high yields (up to 97%) and high enantioselectivities (up to 95% ee). The reaction provides an efficient method for preparing bifunctional compounds with a chiral quaternary

  开发了由手性螺亚磷酰胺配体的镍配合物催化的甲硅烷基保护的烯丙基醇的不对称氢乙烯基化反应。以高收率（高达97％）和高对映选择性（高达ee的95％）生产了一系列具有手性四元中心的均丙醇。该反应提供了制备具有手性季碳中心的双官能化合物的有效方法。
• Kobayashi,M. et al., Chemical and pharmaceutical bulletin, 1972, vol. 20, p. 1898 - 1905
  作者：Kobayashi,M. et al.

  DOI：——

  日期：——
• LU M. C.; SHIH L. B.; JAE H. S.; GEARIEN J. E.; THOMPSON E. B., J. MED. CHEM., 30,(1987) N 2, 424-427
  作者：LU M. C.、 SHIH L. B.、 JAE H. S.、 GEARIEN J. E.、 THOMPSON E. B.

  DOI：——

  日期：——

表征谱图