(1S)-1-[6-[[tert-butyl(dimethyl)silyl]oxymethyl]pyridin-2-yl]ethanol | 162238-16-6

• 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: (1S)-1-[6-[[tert-butyl(dimethyl)silyl]oxymethyl]pyridin-2-yl]ethanol
• CAS: 162238-16-6
• 化学式: C₁₄H₂₅NO₂Si
• 分子量: 267.443
• InChiKey: DTBGDHOXISCIIO-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S)-1-[6-[[tert-butyl(dimethyl)silyl]oxymethyl]pyridin-2-yl]ethanol 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.92h， 生成 bis[[6-[(1S)-1-hexadecanoyloxyethyl]pyridin-2-yl]methyl] pyridine-2,6-dicarboxylate
  参考文献：
  名称：

  Ag⁺-Specific Pyridine Podands:  Effects of Ligand Geometry and Stereochemically Controlled Substitution on Cation Complexation and Transport Functions

  摘要：

  A new series of acyclic podands was designed so that three pyridine moieties cooperatively bind a guest Ag(+). Liquid-Liquid extraction, NMR binding, and computer calculation experiments reveal that podands with three pyridine donors in a proper geometry exhibit a perfect Ag(+) specificity. They selectively extracted Ag+ in the presence of equimolar Pb(2+), CU(2+), Ni(2+), Co(2+), and Zn(2+). Introduction of two chiral centers close to the pyridine binding sites surprisingly influences the Ag(+)-binding ability of the podand. Fourteen new pyridine podands were evaluated as carriers in a liquid membrane transport system. A combination of ligand geometry and stereocontrolled substitution provides excellent Ag(+)-specific transport.

  DOI：

  10.1021/jo9721148
• 作为产物：
  描述：

  (rac)-1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-yl]-ethanol 生成 (1S)-1-[6-[[tert-butyl(dimethyl)silyl]oxymethyl]pyridin-2-yl]ethanol
  参考文献：
  名称：

  吡啶基和联吡啶基乙醇的旋光拆分和光学纯寡吡啶的简便制备

  摘要：

  南极假丝酵母脂肪酶和乙酸乙烯酯在二异丙醚中进行消旋吡啶基和联吡啶乙醇的动力学拆分，其中（R）-醇被立体选择性乙酰化，乙酸酯2和剩余的（S）-醇1均获得了较高的收率。对映体过量。通过（S）-1b和（S）-1e与乙基联吡啶亚砜的偶联反应制备了（S 0-低级吡啶基乙醇，7和8。

  DOI：

  10.1016/0040-4039(94)80025-1

文献信息

• Chiral Pyridines:  Optical Resolution of 1-(2-Pyridyl)- and 1-[6-(2,2‘-Bipyridyl)]ethanols by Lipase-Catalyzed Enantioselective Acetylation
  作者：Jun'ichi Uenishi、Takao Hiraoka、Shinichiro Hata、Kenji Nishiwaki、Osamu Yonemitsu、Kaoru Nakamura、Hiroshi Tsukube

  DOI：10.1021/jo971521g

  日期：1998.4.1

  The resolution of racemic 1-(2-pyridyl)ethanols 2a-n, including the 2,2'-bipyridyl and isoquinolyl derivatives, by lipase-catalyzed asymmetric acetylation with vinyl acetate is reported. The reactions were carried out in diisopropyl ether at either room temperature or 60 degrees C using Candida antarctica lipase (CAL) to give (R)-acetate and unreacted (S)-alcohol with excellent enantiomeric purities

  据报道，外消旋的1-（2-吡啶基）乙醇2a-n（包括2,2'-联吡啶基和异喹啉基衍生物）通过脂肪酶催化乙酸乙烯酯的不对称乙酰化而得到拆分。反应在室温或60℃下使用南极假丝酵母脂肪酶（CAL）在二异丙醚中进行，以良好的收率得到具有优异对映体纯度的（R）-乙酸酯和未反应的（S）-醇。对于在吡啶环的6位带有sp（3）型碳的底物，如2c，2d和2e，在室温下具有1-羟丙基和烯丙基的底物，在室温下反应速率相对较慢。吡啶环上的2位，例如2l和2m。在这种情况下，需要更高的温度。因此，当反应在60摄氏度下进行时，在不丧失高对映体特异性的情况下将其加速了3至7倍。然而，即使当在60℃下反应持续更长的时间时，均丙醇2n的反应仍未完成。该酶拆分实际上可用于从10mg至10g或从10mg至10g的较宽反应规模。更多。该催化剂可重复使用，每次使用会损失5-10％的初始活性。
• Identification and synthesis of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to the α2δ-1 subunit of voltage gated calcium channel
  作者：Alec D. Lebsack、Janet Gunzner、Bowei Wang、Richard Pracitto、Hervé Schaffhauser、Angelina Santini、Jayashree Aiyar、Robert Bezverkov、Benito Munoz、Wensheng Liu、Shankar Venkatraman

  DOI：10.1016/j.bmcl.2004.03.008

  日期：2004.5

  We have identified and synthesized a series of [1,2,4]triazolo[3,4-a]phthalazine derivatives as high-affinity ligands to alpha(2)delta-1 subunit of voltage gated calcium channels. Structure-activity relationship studies directed toward improving the potency and physical properties of 2 lead to the discovery of 20 (IC50 = 15 nM) and (S)-22 (IC50 = 30 nM). A potent and selective radioligand, [H-3]-(S)-22 was also synthesized to demonstrate that this ligand binds to the same site as gabapentin. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of Optically Pure 1-(2-Pyridinyl)ethylamine and 4-(2-Pyridinyl)-1,3-oxazolin-2-one
  作者：Jun'ichi Uenishi、Takao Hiraoka、Kyoko Yuyama、Osamu Yonemitsu

  DOI：10.3987/com-99-s78

  日期：——

  Several (R)-1-(2-pyridinyl)ethylamines (4) were prepared from (S)-1-(2-pyridinyl)ethanols (L) with complete inversion of the chiral center. Substitution of (S)-1-(2-pyridinyl)ethyl methanesulfonate (2) with sodium azide gave (R)-1-(2pyridinyl)ethyl azide (3) stereospecifically, and reduction of the azide afforded the corresponding amine (4) in good yield. When optically pure 2-silyloxy-1-(2-piridinyl)ethanol was used, 2-silyloxy-1-(2-pyridinyl)ethylamine was obtained, and this was converted to optically pure pyridine-substituted 1,3-oxazolidin-2-one at the 4-position.