(S)-1-(3-苯腈)乙醇 | 258525-51-8

• 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: (S)-1-(3-苯腈)乙醇
• 英文名称: (S)-1-(3-cyanophenyl)ethanol
• 英文别名: 3-[(1S)-1-hydroxyethyl]benzonitrile；(S)-1-(3’-cyanophenyl)ethanol；(S)-3-(1-hydroxyethyl)benzonitrile
• CAS: 258525-51-8
• 化学式: C₉H₉NO
• mdl: MFCD18339562
• 分子量: 147.177
• InChiKey: ZGFGALOARUPOBS-ZETCQYMHSA-N

物化性质

• 沸点：
  267℃
• 密度：
  1.12
• 闪点：
  115℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-(3-苯腈)乙醇 在 盐酸 、 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 生成 3-{(1S)-1-[(2-chloro-7-{[(2R)-1-hydroxypentan-2-yl]amino}[1,3]thiazolo[4,5-d]pyrimidin-5-yl)sulfanyl]ethyl}benzonitrile
  参考文献：
  名称：

  Substituted 7-Amino-5-thio-thiazolo[4,5-d]pyrimidines as Potent and Selective Antagonists of the Fractalkine Receptor (CX₃CR1)

  摘要：

  We have developed two parallel series, A and B, of CX(3)CR1 antagonists for the treatment of multiple sclerosis. By modifying the substituents on the 7-amino-5-thio-thiazolo[4,5-d]-pyrimidine core structure, we were able to achieve compounds with high selectivity for CX(3)CR1 over the closely related CXCR2 receptor. The structure-activity relationships showed that a leucinol moiety attached to the core-structure in the 7-position together with alpha-methyl branched benzyl derivatives in the 5-position displayed promising affinity, and selectivity as well as physicochemical properties, as exemplified by compounds 18a and 24h. We show the preparation of the first potent and selective orally available CX(3)CR1 antagonists.

  DOI：

  10.1021/jm3012273
• 作为产物：
  描述：

  3-乙酰苯腈 在 tris(2,2'-bipyridyl)ruthenium dichloride 、 葡萄糖 、 β-烟酰胺腺嘌呤二核苷酸 、 Bacillusa myloliquefaciens flavin-dependent nitroreductase BaNTR₁ 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以98%的产率得到
  参考文献：
  名称：

  化学和对映选择性光酶促酮还原使用混杂的黄素依赖性硝基还原酶

  摘要：

  报道了使用混杂的硝基还原酶 BaNTR1 将多种酮类的对映选择性光酶还原为相应的醇类。这种黄素酶不仅表现出出色的对映选择性，而且还具有非常高的化学选择性，促进各种 α,β-不饱和酮的光酶还原，得到所需的对映富集醇，而不会还原 C=C 或 C≡C 键。

  DOI：

  10.1002/cctc.202200043

文献信息

• Enzymatic reduction of acetophenone derivatives with a benzil reductase from Pichia glucozyma (KRED1-Pglu): electronic and steric effects on activity and enantioselectivity
  作者：Martina L. Contente、Immacolata Serra、Luca Palazzolo、Chiara Parravicini、Elisabetta Gianazza、Ivano Eberini、Andrea Pinto、Benedetta Guidi、Francesco Molinari、Diego Romano

  DOI：10.1039/c6ob00047a

  日期：——

  (KRED1-Pglu) was used for the enantioselective reduction of various mono-substituted acetophenones. Reaction rates of meta- and para-derivatives were consistent with the electronic effects described by σ-Hammett coefficients; on the other hand, enantioselectivity was determined by an opposite orientation of the substrate in the binding pocket. Reduction of ortho-derivatives occurred only with substrates

  来自葡糖毕赤酵母的重组酮还原酶（KRED1-Pglu）被用于对映选择性还原各种单取代的苯乙酮。的反应速率元-和对位-衍生物是与所描述的电子效果一致σ -Hammett系数; 另一方面，对映选择性由结合口袋中底物的相反方向决定。仅在带有低空间影响的取代基（即F和CN）的底物上发生邻位衍生物的还原。反应性受立体电子特征控制（CO长度和电荷，LUMO前沿分子轨道的形状），可以从理论上计算出来。
• Nickel(II)‐Dipyridylphosphine‐Catalyzed Enantioselective Hydrosilylation of Ketones in Air
  作者：Fei‐Fei Wu、Ji‐Ning Zhou、Qiang Fang、Yi‐Hu Hu、Shijun Li、Xi‐Chang Zhang、Albert S. C. Chan、Jing Wu

  DOI：10.1002/asia.201200512

  日期：2012.11

  dipyridylphosphine ligand, as well as the stoichiometric hydride source PhSiH3, formed an effective catalyst system for the NiII‐catalyzed asymmetric hydrosilylation of a diverse range of electron‐deficient aryl alkyl ketones with enantioselectivities up to 90 % ee. The practical potential of the protocol was evinced by its good air‐stability.

  空气稀薄：催化量的镍（II）盐和非外消旋二吡啶膦配体以及化学计量的氢化物源PhSiH 3形成了有效的催化剂体系，用于Ni II催化的各种电子形式的不对称氢化硅烷化反应不足的对映选择性高达90％ee的芳基烷基酮。良好的空气稳定性证明了该协议的实际潜力。
• [EN] MACROCYCLIC INHIBITORS OF MYELOPEROXIDASE<br/>[FR] INHIBITEURS MACROCYCLIQUES DE MYELOPEROXIDASE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018005336A1

  公开（公告）日：2018-01-04

  The present invention provides compounds of Formula (I): wherein the substituents are as defined in the specification, and compositions comprising any of such novel compounds. These compounds are myeloperoxidase (MPO) inhibitors and/or eosinophil peroxidase (EPX) inhibitors, and may be useful for for the treatment and/or prophylaxis of atherosclerosis, heart failure, chronic obstructive pulmonary disease (COPD), and related diseases.

  本发明提供了式（I）的化合物：其中取代基如规范中所定义，并包括任何此类新化合物的组合物。这些化合物是髓过氧化物酶（MPO）抑制剂和/或嗜酸性粒细胞过氧化物酶（EPX）抑制剂，可能对动脉粥样硬化、心力衰竭、慢性阻塞性肺病（COPD）及相关疾病的治疗和/或预防有用。
• Novel 5-Substituted 7-Amino-[1,3]Thiazolo[4,5-D]Pyrimidine Derivatives 793
  申请人：Nordvall Gunnar

  公开号：US20080214578A1

  公开（公告）日：2008-09-04

  There are disclosed novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives of formula (I) wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined in the specification, and pharmaceutically acceptable salts thereof, together with processes for their preparation, pharmaceutical compositions comprising them and their use in therapy. The compounds of formula (I) are CX 3 CR1 receptor antagonists and are thereby particularly useful in the treatment or prophylaxis of neurodegenerative disorders, demyelinating disease, cardio- and cerebrovascular atherosclerotic disorders, peripheral artery disease, rheumatoid arthritis, pulmonary diseases such as COPD, asthma or pain.

  公开了一种新的5-取代的7-氨基-[1,3]噻唑[4,5-d]嘧啶衍生物的公式(I)，其中R1、R2、R3、R4和R5如规范中所定义，并且其药学上可接受的盐，以及其制备方法、包含它们的药物组合物和它们在治疗中的用途。公式(I)化合物是CX3CR1受体拮抗剂，因此在治疗或预防神经退行性疾病、脱髓鞘性疾病、心血管和脑血管动脉粥样硬化性疾病、周围动脉疾病、类风湿性关节炎、慢性阻塞性肺疾病、哮喘或疼痛等方面特别有用。
• Novel 5,7-Disubstituted [1,3]Thiazolo[4,5-D]Pyrimidin-2(3H)-One Derivatives 794
  申请人：Nordvall Gunnar

  公开号：US20090124637A1

  公开（公告）日：2009-05-14

  There are disclosed novel 5,7-disubstituted [1,3]thiazolo[4,5-d]pyrimidin-2(3H)-one derivatives of formula (I) [Chemical formula should be inserted here. Please see paper copy] wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined in the specification, and pharmaceutically acceptable salts thereof, together with processes for their preparation, pharmaceutical compositions comprising them and their use in therapy. The compounds of formula (I) are CX 3 CR 1 receptor antagonists and are thereby particularly useful in the treatment or prophylaxis of neurodegenerative disorders, demyelinating disease, cardio- and cerebrovascular atherosclerotic disorders, peripheral artery disease, rheumatoid arthritis, pulmonary diseases such as COPD, asthma or pain.

  本文揭示了新颖的5,7-二取代[1,3]噻唑并[4,5-d]嘧啶-2(3H)-酮衍生物的公式(I) [化学式应在此处插入。请参见纸质复印件]，其中R1、R2、R3、R4和R5如规范中定义的那样，以及其药学上可接受的盐，以及它们的制备方法、包含它们的制剂和它们在治疗中的用途。公式(I)化合物是CX3CR1受体拮抗剂，因此在神经退行性疾病、脱髓鞘疾病、心脑血管动脉粥样硬化性疾病、周围动脉疾病、类风湿性关节炎、COPD、哮喘或疼痛的治疗或预防中特别有用。