(S)-2-methyl-1-(3-pyridyl)propan-1-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-2-methyl-1-(3-pyridyl)propan-1-ol
• 英文别名: (S)-2-methyl-1-(pyridin-3-yl)propan-1-ol；2-methyl-1-(pyridin-3-yl)propan-1-ol；(1S)-2-methyl-1-pyridin-3-ylpropan-1-ol
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: MURQWXKMHQTOOL-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基-1-(3-吡啶基)-1-丙酮 在 Almag CRED A₁₃₁ 、 NADP 、 glucose dehydrogenase 作用下， 以 水 、 二甲基亚砜 、 异丙醇 为溶剂， 以94%的产率得到(S)-2-methyl-1-(3-pyridyl)propan-1-ol
  参考文献：
  名称：

  Preparative access to medicinal chemistry related chiral alcohols using carbonyl reductase technology

  摘要：

  Libraries of highly enantioenriched secondary alcohols in both enantiomeric forms were synthesised by enzymatic reduction of their parent ketones using selectAZyme (TM) carbonyl reductase (CRED) technology. Commercially available CREDs were able to reduce a range of substrate classes efficiently and with very high enantioselectivity. Matching substrate classes to small subsets of CREDs enabled the fast development of preparative bioreductions and the rapid generation of 100-1500 mg samples of chiral alcohols in typically >95% ee and the majority in >= 99.0% ee. The conditions for small scale synthesis were then scaled up to 0.5 kg to deliver one of the chiral alcohols, (S)-1-(4-bromophenyl)-2-chloroethanol, in 99.8% ee and 91% isolated yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.015

文献信息

• Structural Contributions to Autocatalysis and Asymmetric Amplification in the Soai Reaction
  作者：Soumitra V. Athavale、Adam Simon、K. N. Houk、Scott E. Denmark

  DOI：10.1021/jacs.0c05994

  日期：2020.10.28

  autocatalysis, providing insights into the role played by reactant and alkoxide structure. The alkynyl substituent favorably tunes catalyst solubility, aggregation, and conformation while modulating substrate reactivity and selectivity. The alkyl groups and the heteroaromatic core play further complementary roles in catalyst aggregation and substrate binding. In the study of these structure-activity relationships

  嘧啶醛的二异丙基锌烷基化反应——Soai 反应，具有放大不对称自催化的惊人特性——在有机化学中占有独特的地位，是机理阐明的一个突出挑战。嘧啶和吡啶系统的“混合催化剂-底物”实验的新范式允许将催化与自动催化断开，从而深入了解反应物和醇盐结构所起的作用。炔基取代基有利于调节催化剂溶解性、聚集和构象，同时调节底物反应性和选择性。烷基和杂芳族核在催化剂聚集和底物结合中发挥进一步的互补作用。在研究这些构效关系时，鉴定了具有放大自催化作用的新型吡啶底物。三种代表连续的氮路易斯碱度强度的自催化系统的比较表明 N-Zn 结合事件的强度是如何影响自催化进程的主要因素。
• Sato, Itaru; Urabe, Hiroki; Ishii, Shinji, Organic Letters, 2001, vol. 3, # 24, p. 3850 - 3854
  作者：Sato, Itaru、Urabe, Hiroki、Ishii, Shinji、Tanji, Shigehisa、Soai, Kenso

  DOI：——

  日期：——
• Asymmetric Addition of Pyridyl Aluminum Reagents to Aldehydes Catalyzed by a Titanium(IV) Catalytic System of (<i>R</i>)-H₈-BINOLate
  作者：Lijun Zhang、Bing Tu、Min Ge、Yimei Li、Liangyu Chen、Wei Wang、Shuangliu Zhou

  DOI：10.1021/acs.joc.5b01410

  日期：2015.8.21

  The asymmetric addition of pyridyl aluminum reagents to aldehydes has been successfully developed by employing a titanium(IV) catalytic system of (R)-H-8-BINOLate, which affords a series of valuable optically active diarylmethanols containing various pyridyl groups in high yields with excellent enantioselectivities of up to 98% ee.
• SOAI, KENSO;NIWA, SEIJI;HORI, HIROSHI, J. CHEM. SOC. CHEM. COMMUN.,(1990) N4, C. 982-983
  作者：SOAI, KENSO、NIWA, SEIJI、HORI, HIROSHI

  DOI：——

  日期：——
• Preparative access to medicinal chemistry related chiral alcohols using carbonyl reductase technology
  作者：Andrew S. Rowan、Thomas S. Moody、Roger M. Howard、Toby J. Underwood、Iain R. Miskelly、Yanan He、Bo Wang

  DOI：10.1016/j.tetasy.2013.09.015

  日期：2013.11

  Libraries of highly enantioenriched secondary alcohols in both enantiomeric forms were synthesised by enzymatic reduction of their parent ketones using selectAZyme (TM) carbonyl reductase (CRED) technology. Commercially available CREDs were able to reduce a range of substrate classes efficiently and with very high enantioselectivity. Matching substrate classes to small subsets of CREDs enabled the fast development of preparative bioreductions and the rapid generation of 100-1500 mg samples of chiral alcohols in typically >95% ee and the majority in >= 99.0% ee. The conditions for small scale synthesis were then scaled up to 0.5 kg to deliver one of the chiral alcohols, (S)-1-(4-bromophenyl)-2-chloroethanol, in 99.8% ee and 91% isolated yield. (C) 2013 Elsevier Ltd. All rights reserved.