ethyl (S)-atrolactate

• 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: ethyl (S)-atrolactate
• 英文别名: (S)-ethyl 2-hydroxy-2-phenylpropanoate；Aethyl-L-atrolactat；L-Atrolactinsaeure-aethylester；(S)-2-hydroxy-2-phenyl-propionic acid ethyl ester；(S)-2-Hydroxy-2-phenyl-propionsaeure-aethylester；Ethyl (S)-2-hydroxy-2-phenylpropanoate；ethyl (2S)-2-hydroxy-2-phenylpropanoate
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: ZYBCQQMOAQEIKV-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  ethyl (S)-atrolactate 在 氯化亚砜 、 乙醇 、 镍 作用下， 生成 ethyl (S)-2-phenylpropionate
  参考文献：
  名称：

  Assessment of ampulla (Takotsubo) cardiomyopathy with coronary angiography, two-dimensional echocardiography and99mTc-tetrofosmin myocardial single photon emission computed tomography

  摘要：

  We studied the causative mechanism of ampulla (Takotsubo) cardiomyopathy. Methods: We examined 7 patients with ampulla cardiomyopathy by means of coronary angiography, two-dimensional echocardiography and Tc-99m-tetrofosmin myocardial SPECT at the time of emergency admission (acute phase), at 3 to 5 days after the attack (subacute phase) and at 1 month after the attack (chronic phase). The left ventricle was divided into 9 regions on two-dimensional echocardiograms and Tc-99m-tetrofosmin myocardial SPECT images, then the degree of abnormalities in each region was scored in four grades from normal (0) to severely abnormal (3). We injected nicorandil into the coronary arteries and determined the elevation in the ST segment before and after administration. Results: Coronary angiography did not show stenotic lesions in any patient. The acute, subacute and chronic phase myocardial perfusion scores on Tc-99m-tetrofosmin myocardial SPECT were 11.2 +/- 3.4, 2.7 +/- 2.3 and 0.4 +/- 0.5, respectively, and wall motion scores on echocardiograms were 13.0 +/- 3.6, 4.4 +/- 2.2 and 0.6 +/- 0.6, respectively, indicating improvement in all scores during the subacute phase (p < 0.01). The elevation in the ST segment (mm) on the electrocardiogram was improved from 8.3 +/- 2.7 to 4.9 +/- 1.9 after the administration of nicorandil (p < 0.05). Conclusion: These findings indicated that coronary microvascular spasm is one causative mechanism of ampulla cardiomyopathy.

  DOI：

  10.1007/bf02988242
• 作为产物：
  描述：

  (S)-2-Phenyl-2-(tetrahydro-pyran-2-yloxy)-propionic acid ethyl ester 在 CuCl₂*H₂O 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以91%的产率得到ethyl (S)-atrolactate
  参考文献：
  名称：

  氯化铜 (II) 二水合物：四氢吡喃醚 (THP 醚) 和 1-乙氧基乙基醚 (EE 醚) 脱保护的催化剂

  摘要：

  四氢吡喃基醚（THP 基团）和 1-乙氧基乙基醚（EE 基团）在 95% EtOH 或 Me2CO-H2O (95:5) 中在催化量的氯化铜 (II) 二水合物（2-5摩尔％）。

  DOI：

  10.1039/a900262f

文献信息

• Isothiourea‐Catalyzed Acylative Kinetic Resolution of Tertiary α‐Hydroxy Esters
  作者：Shen Qu、Samuel M. Smith、Víctor Laina‐Martín、Rifahath M. Neyyappadath、Mark D. Greenhalgh、Andrew D. Smith

  DOI：10.1002/anie.202004354

  日期：2020.9.14

  acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols

  已开发出高度对映选择性的异硫脲催化的无环叔醇的酰基动力学拆分（KR）。对于带有相邻酯取代基的叔醇的KR，选择性因子高达200，反应转化率和对映体选择性均对立体异构叔丁醇中心的空间和电子环境敏感。对于空间上更拥挤的醇，最合适的方法是使用最新开发的异硒脲催化剂，对映选择性相当，但与异硫脲HyperBTM相比，转化率更高。非对映体酰化过渡态模型被提出以合理化此过程中对映歧化的起源。
• Enantioselective Addition of Dimethylzinc to α-Keto Esters
  作者：José Pedro、Gonzalo Blay、Isabel Fernández、Alícia Marco-Aleixandre

  DOI：10.1055/s-2007-983851

  日期：2007.12

  The readily available (+)-N-Benzyl-(S)-mandelamide catalyzes the enantioselective addition of dimethylzinc to α-keto esters to give α-methyl-α-hydroxy esters containing stereogenic quaternary centers with moderate to good yields (56-87%). A good enantioselectivity of the reaction is obtained for aryl and heteroaryl keto esters. For these substrates ee values of 75-90% are obtained. The enantioselectivity

  容易获得的 (+)-N-苄基-(S)-扁桃酰胺催化二甲基锌与 α-酮酯的对映选择性加成，得到含有立体季铵中心的 α-甲基-α-羟基酯，产率适中至高 (56-87 %）。对于芳基和杂芳基酮酯，反应具有良好的对映选择性。对于这些基材，获得了 75-90% 的 ee 值。对于带有脂肪链的底物，对映选择性稍低。
• Enantioselective synthesis of quaternary stereogenic centers through catalytic asymmetric addition of dimethylzinc to α-ketoesters with chiral cis-cyclopropane-based amide alcohol as ligand
  作者：Bing Zheng、Shicong Hou、Zhiyuan Li、Hongchao Guo、Jiangchun Zhong、Min Wang

  DOI：10.1016/j.tetasy.2009.07.050

  日期：2009.9

  A new amino alcohol with a chiral cyclopropane backbone has been developed and used in the catalytic asymmetric diethylzinc addition to various types of α-ketoesters. This cyclopropane-based chiral amino alcohol shows moderate enantioselectivity in the addition of organozinc to α-ketoesters. For dimethylzinc addition to α-ketoesters, up to 81% ee are obtained, respectively.

  已开发出具有手性环丙烷骨架的新型氨基醇，并将其用于催化不对称二乙基锌除各种类型的α-酮酸酯中。这种基于环丙烷的手性氨基醇在将有机锌添加到α-酮酸酯中时显示出中等的对映选择性。对于将二甲基锌添加到α-酮酸酯中，分别获得了高达81％的ee。
• Highly Homogeneous Stereocontrolled Construction of Quaternary Hydroxyesters by Addition of Dimethylzinc to α-Ketoesters Promoted by Chiral Perhydrobenzoxazines and B(OEt)3
  作者：Rebeca Infante、Javier Nieto、Celia Andrés

  DOI：10.1002/chem.201102913

  日期：2012.4.2

  A highly efficient enantioselective addition of Me2Zn to α‐ketoesters, assisted by a chiral perhydro‐1,3‐benzoxazine ligand, is described. This novel catalytic system offers homogeneous elevated enantioselectivities in the preparation of α‐hydroxyesters that bear a quaternary stereocenter, with a minor dependence on electronic and steric effects when aromatic, heteroaromatic, or aliphatic α‐ketoesters

  描述了在手性过氢-1,3-苯并恶嗪配体的协助下，高效地将Me 2 Zn对映体选择性地添加到α-酮酸酯中。这种新型的催化体系在制备具有季立体中心的α-羟基酯时，提供了均相的提高的对映选择性，当使用芳族，杂芳族或脂族α-酮酯时，对电子和空间效应的依赖性较小。催化剂可被回收和再利用而不会损失活性。
• Affinity and selectivity of the optical isomers of 3-quinuclidinyl benzilate and related muscarinic antagonists
  作者：W. Janusz Rzeszotarski、Daniel W. McPherson、John W. Ferkany、William J. Kinnier、Lalita Noronha-Blob、Alicja Kirkien-Rzeszotarski

  DOI：10.1021/jm00402a035

  日期：1988.7

  All of the optical isomers of the muscarinic antagonists 3-(1-azabicyclo[2.2.2]octyl) alpha-hydroxy-alpha,alpha-diphenylacetate (3-quinuclidinyl benzilate, QNB, 1) 3-(1-azabicyclo[2.2.2]octyl) xanthene-9-carboxylate (3-quinuclidinyl xanthene-9-carboxylate, QNX, 2), and 3-(1-azabicyclo[2.2.2]ocytl) alpha-hydroxy-alpha-phenylpropionate (3-quinuclidinyl atrolactate, QNA, 3) were prepared and studied in

  毒蕈碱拮抗剂3-（1-氮杂双环[2.2.2]辛基）α-羟基-α，α-二苯乙酸酯（3-喹啉基苯甲酸根，QNB，1）3-（1-氮杂双环[2.2。]的所有旋光异构体。 2]辛基）氧杂蒽9-羧酸盐（3-奎宁环烯基氧杂蒽9-羧酸盐，QNX，2）和3-（1-氮杂双环[2.2.2] ocytl）α-羟基-α-苯基丙酸酯（3-奎宁环戊基丙酸酯） ，QNA，3）被制备并在结合和功能测定中研究。在所有情况下，（R）-1-氮杂双环[2.2.2] octan-3-ol（3-quinuclidinol）的酯对毒蕈碱乙酰胆碱受体（M-AChRs）的M1和M2亚群具有更大的亲和力同行。QNB（1），QNX（2）和QNA（3）的对映异构体（其中毒蕈碱拮抗剂的醇部分具有S绝对立体化学）对M1-AChR更具选择性。该选择性是通过性质（在QNA的情况下）是酸部分的手性来调节的。该系列中最有效的异构体是（R）-Q​​NB。在QN