(2S,2'S)-1,1'-(+)-oxybis(2-propanol) | 61217-63-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,2'S)-1,1'-(+)-oxybis(2-propanol)
• 英文别名: (S,S)-(+)-bis(2-hydroxypropyl) ether；(S,S)-1,1'-oxy-bis-propan-2-ol；(2S)-1-[(2S)-2-hydroxypropoxy]propan-2-ol
• CAS: 61217-63-8
• 化学式: C₆H₁₄O₃
• 分子量: 134.175
• InChiKey: AZUXKVXMJOIAOF-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,2'S)-1,1'-(+)-oxybis(2-propanol) 在 盐酸 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 40.5h， 生成 (3S,6S,10S,13S)-(-)-3,6,10,13-tetramethyl-2,5,8,11,14-pentaoxapentadecane
  参考文献：
  名称：

  Alkali metals dissolved in optically active solvents

  摘要：

  DOI：

  10.1021/jo00323a026
• 作为产物：
  描述：

  L-乳酸 生成 (2S,2'S)-1,1'-(+)-oxybis(2-propanol)
  参考文献：
  名称：

  Stereochemical factors in epoxide polymerization by base and coordination catalysts

  摘要：

  DOI：

  10.1021/ja00766a052

文献信息

• Novel synthesis of chiral, enantiomerically pure thiodiglycols and diglycols
  作者：Jens Christoffers、Ulrich Rößler

  DOI：10.1016/s0957-4166(98)00224-9

  日期：1998.7

  converted in a sequence of O-protection, reduction, O-activation, thioether and ether formation and deprotection to chiral, non-racemic β,β′-dihydroxy thioethers 1a, 1b and ether 1c. Overall yields are excellent (75%). In an attempt to synthesize the respective dihydroxy ether 1d derived from mandelic acid 1,3-dioxolane derivatives 7 were obtained.

  天然α-羟基酸已经按照O-保护，还原，O-活化，硫醚和醚形成和脱保护的顺序转化为手性，非外消旋的β，β'-二羟基硫醚1a，1b和醚1c。总体收率极好（75％）。为了合成相应的衍生自扁桃酸1，3-二氧戊环衍生物7的二羟基醚1d。
• Enzymatic resolution of propylene glycol alkyl (or aryl) ethers and ether acetates
  申请人：Resnick M Sol

  公开号：US20050026260A1

  公开（公告）日：2005-02-03

  Glycol ether acetates, and in particular propylene glycol alkyl (or aryl) ether acetates, can be resolved enzymatically by enantioselective hydrolysis with a hydrolase at high concentrations of substrates; in some embodiments, the hydrolase is a lipase. Glycol ethers, and in particular propylene glycol alkyl (or aryl) ethers, can be resolved enzymatically by enantioselective transesterification with a hydrolase, in the presence of an acyl donor, at high concentrations of substrates; in some embodiments, the hydrolase is a lipase.

  乙二醇醚醋酸酯，特别是丙二醇烷基（或芳基）醚醋酸酯，可以在高底物浓度下通过手性选择性水解酶酶解分离; 在某些实施方案中，水解酶是脂肪酶。乙二醇醚，特别是丙二醇烷基（或芳基）醚，在存在酰基供体的情况下，可以在高底物浓度下通过手性选择性水解酶酶解分离; 在某些实施方案中，水解酶是脂肪酶。
• Chiral Pyridine-Based Macrobicyclic Clefts:  Synthesis and Enantiomeric Recognition of Ammonium Salts
  作者：Paul C. Hellier、Jerald S. Bradshaw、J. Jolene Young、Xian Xin Zhang、Reed M. Izatt

  DOI：10.1021/jo960890u

  日期：1996.1.1

  An achiral (3) and two chiral pyridine-based macrobicyclic clefts (4 and 5) have been prepared by treating 2,6-bis[[2',6'-bis(bromomethyl)-4'-methylphenoxy]pyridine (2) with the appropriate achiral and chiral glycols. Starting 2 was prepared by first treating 2,6-bis(hydroxymethyl)-4-methylphenol with 2,6-[(tosyloxy)methyl]pyridine followed by phosphorus tribromide. Achiral macrobicyclic cleft 3 formed a complex at 25 degrees C in 50% CH3OH/50% CHCl3 (v/v) with a primary ammonium salt (log K=3.15) as evidenced by a significant change in the (1)HNMR spectrum. Highly organized (S,S,S,S)4, prepared by treating 2 with (1S,5S)-3-oxapentane-1,5-diol, exhibited recognition at 25 degrees C in 20% C2H5OH/80% 1,2-C2H4Cl2 (v/v) for the (S)-enantiomer of alpha-(1-naphthyl)-ethylammonium perchlorate (NapEt) over its (R)-form (Delta log K=0.85). This high recognition factor probably reflects an increase in molecular rigidity by the introduction of a second macro ring on the monocyclic pyridinocrown ligand.
• One-Pot Generation and Conversion of Trichloroacetimidates for the Racemization-Free Allylation and Benzylation of α-Hydroxyesters and the Enantiopure Synthesis of a Chiral Diglycole
  作者：Jens Christoffers、Ulrich Rößler

  DOI：10.1002/1521-3897(200009)342:7<654::aid-prac654>3.3.co;2-q

  日期：2000.9

  O-Allylations and O-benzylations of alpha -hydroxy esters (3a-3c) are performed without racemization. The reagents applied, O-allyl- and O-benzyltrichloroacetimidate (5a, 5b) are prepared and converted in a one-pot-procedure. After protection by benzylation (S)-(-)-ethyl lactate (3a) is converted by a sequence of carbonyl reduction, alcohol activation, ether formation, and deprotection to the optically active diglycole derivative 1a.
• Mono- and Bidentate Phosphinanes—New Chiral Ligands and Their Application in Catalytic Asymmetric Hydrogenations
  作者：Markus Ostermeier、Jan Prieß、Günter Helmchen

  DOI：10.1002/1521-3773(20020215)41:4<612::aid-anie612>3.0.co;2-9

  日期：2002.2.15