(R,R)-(+)-2,6-bis(1'-hydroxy-2',2'-dimethylpropyl)pyridine | 156129-01-0

• 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: (R,R)-(+)-2,6-bis(1'-hydroxy-2',2'-dimethylpropyl)pyridine
• 英文别名: 1,1'-(pyridine-2,6-diyl)bis(2,2-dimethylpropan-1-ol)；2R,6R-bis-(2,2-dimethyl-1-hydroxy-1-propyl)pyridine；(1R)-1-[6-[(1R)-1-hydroxy-2,2-dimethylpropyl]pyridin-2-yl]-2,2-dimethylpropan-1-ol
• CAS: 156129-01-0
• 化学式: C₁₅H₂₅NO₂
• 分子量: 251.369
• InChiKey: YHNMSFIVSJLRGC-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯甲基甲基醚 、 (R,R)-(+)-2,6-bis(1'-hydroxy-2',2'-dimethylpropyl)pyridine 在 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以59%的产率得到(R,R)-(+)-2-(1'-hydroxy-2',2'-dimethylpropyl)-6-(1''-methoxymethyloxy-2'',2''-dimethylpropyl)pyridine
  参考文献：
  名称：

  Catalysed asymmetric reaction of aldehydes with dialkylzinc in the presence of chiral pyridyl alcohols as ligands

  摘要：

  The synthesis of homochiral pyridyl alcohols (1,2,3a-c) and a catalytic asymmetric addition of dialkylzinc to various aldehydes using 1-3 as ligands are described. Although the reaction of benzaldehyde with Et2Zn in the presence of (S)-1 and (R,R)-2 gave (S)- and (R)-1-phenyl-1-propanol, respectively, in moderate enantiomeric excess (e.e.), tridentate ligands (3a-c) accelerated the reaction to produce the corresponding alcohols in high e.e. Particularly, (S)-3b was found to be the most efficient catalyst, for which asymmetric reactions of various aldehydes with dialkylzinc gave the corresponding alcohols in good to high e.es. (up to 95% e.e.).

  DOI：

  10.1016/s0957-4166(00)86213-8
• 作为产物：
  描述：

  2,6-bis(2',2'-dimethylpropionyl)pyridine 在 (-)-diisopinocamphenylborane chloride 作用下， 反应 168.0h， 以42%的产率得到(R,R)-(+)-2,6-bis(1'-hydroxy-2',2'-dimethylpropyl)pyridine
  参考文献：
  名称：

  的（1合成，1 '）-2,6-双[1-（二苯基膦基）乙基]吡啶及其在不对称转移氢化的应用

  摘要：

  AC 2对称三齿配体（1R，1R'）2,6-双[1-（二苯基膦基）乙基]吡啶已以对映体纯形式合成。报道了一种合成各种手性吡啶基二醇的实用方法。使用三齿配体实现不对称转移氢化。

  DOI：

  10.1016/0040-4039(95)02298-8

文献信息

• A Highly Active Manganese Catalyst for Enantioselective Ketone and Ester Hydrogenation
  作者：Magnus B. Widegren、Gavin J. Harkness、Alexandra M. Z. Slawin、David B. Cordes、Matthew L. Clarke

  DOI：10.1002/anie.201702406

  日期：2017.5.15

  A new hydrogenation catalyst based on a manganese complex of a chiral P,N,N ligand has been found to be especially active for the hydrogenation of esters down to 0.1 mol % catalyst loading, and gives up to 97 % ee in the hydrogenation of pro‐chiral deactivated ketones at 30–50 °C.

  已发现一种新的基于手性P，N，N配体的锰配合物的加氢催化剂对于酯加氢至低至0.1摩尔％的催化剂负载特别有效，并且在加氢脱氢反应中可产生高达97％ee在30–50°C下手性失活的酮。
• HAWKINS, JOEL M.;SHARPLESS, K. BARRY, TETRAHEDRON LETT., 28,(1987) N 25, 2825-2828
  作者：HAWKINS, JOEL M.、SHARPLESS, K. BARRY

  DOI：——

  日期：——
• Hawkins, Joel M.; Dewan, John C.; Sharpless, K. Barry, Inorganic Chemistry, 1986, vol. 25, # 9, p. 1501 - 1503
  作者：Hawkins, Joel M.、Dewan, John C.、Sharpless, K. Barry

  DOI：——

  日期：——
• Catalysed asymmetric reaction of aldehydes with dialkylzinc in the presence of chiral pyridyl alcohols as ligands
  作者：Miyuki Ishizaki、Ko-ichi Fujita、Mahoko Shimamoto、Osamu Hoshino

  DOI：10.1016/s0957-4166(00)86213-8

  日期：1994.3

  The synthesis of homochiral pyridyl alcohols (1,2,3a-c) and a catalytic asymmetric addition of dialkylzinc to various aldehydes using 1-3 as ligands are described. Although the reaction of benzaldehyde with Et2Zn in the presence of (S)-1 and (R,R)-2 gave (S)- and (R)-1-phenyl-1-propanol, respectively, in moderate enantiomeric excess (e.e.), tridentate ligands (3a-c) accelerated the reaction to produce the corresponding alcohols in high e.e. Particularly, (S)-3b was found to be the most efficient catalyst, for which asymmetric reactions of various aldehydes with dialkylzinc gave the corresponding alcohols in good to high e.es. (up to 95% e.e.).
• Synthesis of (1,1′)-2,6-bis[1-(diphenylphosphino)ethyl]pyridine and its application in asymmetric transfer hydrogenation
  作者：Qiongzhong Jiang、Daniel Van Plew、Shahid Murtuza、Xumu Zhang

  DOI：10.1016/0040-4039(95)02298-8

  日期：1996.2

  A C2 symmetric tridentate ligand, (1R, 1R′) 2,6-Bis[1-(diphenylphosphino)ethyl]pyridine, has been synthesized in enantiomerically pure form. A practical method to synthesize a variety of chiral pyridyl diols is reported. Asymmetric transfer hydrogenation is achieved using the tridentate ligand.

  AC 2对称三齿配体（1R，1R'）2,6-双[1-（二苯基膦基）乙基]吡啶已以对映体纯形式合成。报道了一种合成各种手性吡啶基二醇的实用方法。使用三齿配体实现不对称转移氢化。