(R)-1-methoxy-3-phenyl-2-propanol | 160332-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-methoxy-3-phenyl-2-propanol
• 英文别名: (R)-1-methoxy-3-phenylpropan-2-ol；(2R)-1-methoxy-3-phenylpropan-2-ol
• CAS: 160332-68-3
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: SEKDDNYKSDRFHP-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-methoxy-3-phenyl-2-propanol 、 碘甲烷 在 sodium hydride 作用下， 生成
  参考文献：
  名称：

  Application of pig liver esterase catalyzed transesterification in organic media to the kinetic resolution of glycerol derivatives

  摘要：

  The PLE/MPEG catalyzed transesterification of the glycerol ketals rac-1a and rac-1d-f with vinyl propionate in toluene proceeded with good selectivities (E=24-34) and gave the enantiomerically enriched S-alcohols 1a and 1d-f, and the S-esters 2a and 2d-f. High selectivities (E=99 and E greater than or equal to 200) were observed in the transesterification of the glycerol ether rac-3 and its desoxy analog rac-5, both having a secondary hydroxy group, with PLE/MPEG. In transesterifications in organic media PLE exhibited a much higher enantioselectivity than in hydrolysis in water. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00380-8
• 作为产物：
  描述：

  1-甲氧基-3-苯基-2-丙酮 以20%的产率得到
  参考文献：
  名称：

  Ferraboschi Patrizia, Grisenti Paride, Manzocchi Ada, Santaniello Enzo, Tetrahedron, 50 (1994) N 35, S 10539-10548

  摘要：

  DOI：

文献信息

• Zinc triflate–bis-oxazoline complexes as chiral catalysts: enantioselective reduction of α-alkoxy-ketones with catecholborane
  作者：Marco Bandini、Pier Giorgio Cozzi、Meri de Angelis、Achille Umani-Ronchi

  DOI：10.1016/s0040-4039(99)02339-4

  日期：2000.3

  A new methodology for the catalytic enantioselective reduction of α-alkoxy-ketones is described. The procedure employes Zn(OTf)2–bis-oxazoline complexes (8–10 mol%) as catalysts and catecholborane as the reducing agent. The reaction, carried out in CH2Cl2 at 0°C, affords the α-alkoxy-alcohols in high yields and with good enantioselectivity.

  描述了催化α-烷氧基-酮的对映选择性还原的新方法。该方法使用Zn（OTf）2-双-恶唑啉配合物（8-10 mol％）作为催化剂，儿茶酚硼烷作为还原剂。该反应在0℃下在CH 2 Cl 2中进行，以高收率和良好的对映选择性提供了α-烷氧基醇。
• Activation of Pig Liver Esterase in Organic Media with Organic Polymers. Application to the Enantioselective Acylation of Racemic Functionalized Secondary Alcohols
  作者：Hans-Joachim Gais、Manfred Jungen、Vasudev Jadhav

  DOI：10.1021/jo0016881

  日期：2001.5.1

  the aldehyde and the acid through imine formation and neutralization, respectively, but replenish at least in part also the water consumed in the competing hydrolysis of the acyl donor. A recovery of PLE together with the polymer was achieved without major loss of activity through their immobilization on a water-saturated polyaramide membrane, which occurs spontaneously in organic solvents.

  猪肝酯酶（PLE）在有机溶剂中几乎没有醇与乙烯基酯酰化的活性。但是，在低水含量的有机溶剂中，添加甲氧基聚乙二醇（MPEG），牛血清白蛋白（BSA），TentaGelAmino树脂（TGA）或氨基甲基聚苯乙烯（AMPS）可使PLE与丙酸乙烯酯酰化醇的活性。 。聚合物活化的PLE在外消旋的1-烷氧基-，1-乙基硫烷基-和1-氟-3-芳基-2-丙醇以及外消旋的1-苯氧基-2-丙醇的酰化反应中显示出高对映选择性（E> 100）和外消旋的1-甲氧基-2-苯氧基-2-丙醇。聚合物活化的PLE的合成效用已通过1-甲氧基-3-苯基-2-丙醇，1-乙基硫烷基-3-苯基-2-丙醇，1-甲氧基-3-对羟基苯甲酸酯的克级分辨率证明。甲氧基苯基-2-丙醇，1-氟-3-苯基-2-丙醇，和1-甲氧基-3-苯氧基-2-丙醇。在醇与丙酸乙烯酯的PLE催化的酰化反应中，副产物乙醛和丙酸均对酶有害。另外，由于酰基供体的竞争性酶
• Baker's yeast-mediated reduction of α-hydroxy ketones and derivatives: The steric course of the biotransformation
  作者：Patrizia Ferraboschi、Paride Grisenti、Ada Manzocchi、Enzo Santaniello

  DOI：10.1016/s0040-4020(01)89594-6

  日期：1994.1

  The results from the baker's yeast-mediated reduction of the acetates 3a-d and the methyl ethers 5a-d were compared with the same biotransformation which converts the α-hydroxy ketones 1a-d into the (R)-diols 2a-d (90–98%ee); the acetates 3a-d afford the (S)-monoacetates 4a-d (72–94% ee) and the methyl ethers 5a-d are reduced to the (R)-monoethers 6a-d (64–76% ce).

  将面包师酵母介导的乙酸盐3a-d和甲基醚5a-d还原的结果与将α-羟基酮1a-d转化为（R）-二醇2a-d的相同生物转化进行了比较（90 –98％ee）; 醋酸盐3a-d提供（S）-单乙酸盐4a-d（72-94％ee），甲基醚5a-d还原为（R）-单醚6a-d（64-76％ce）。
• Enantioselective Ring-Opening Reaction of Epoxides with MeOH Catalyzed by Homochiral Metal–Organic Framework
  作者：Koichi Tanaka、Ken-ichi Otani、Takanori Murase、Shyota Nishihote、Zofia Urbanczyk-Lipkowska

  DOI：10.1246/bcsj.20110392

  日期：2012.6.15

  Two new copper metal–organic frameworks containing 2,2′-dihydroxy-1,1′-binaphthalene-5,5′-dicarboxylic acid (5,5′-H2BDA) and 2,2′-dihydroxy-1,1′-binaphthalene-4,4′-dicarboxylic acid (4,4′-H2BDA) have been prepared. X-ray structure determination of [Cu2(5,5′-BDA)2(H2O)2]·MeOH·2H2O (MOF-1) and [Cu2(4,4′-BDA)2(H2O)2]·4H2O (MOF-2) revealed similar 2D sheet structures, containing square-grid coordination networks, but differences in the stacking motif. The desolvated MOF-1 and -2 were used as Lewis acid catalysts in the asymmetric ring-opening reaction of epoxides with MeOH.

  含有 2,2′-二羟基-1,1′-萘-5,5′-二甲酸（5、5′-H2BDA）和 2,2′-二羟基-1,1′-联萘-4,4′-二羧酸（4,4′-H2BDA）。对[Cu2(5,5′-BDA)2(H2O)2]-MeOH-2 （MOF-1）和[Cu2(4,4′-BDA)2( )2]-4 （MOF-2）进行的 X 射线结构测定显示，它们具有相似的二维薄片结构，包含方格配位网络，但在堆积模式上存在差异。脱溶的 MOF-1 和 -2 被用作路易斯酸催化剂，用于环氧化物与 MeOH 的不对称开环反应。
• Lee, Yunmi; Hoveyda, Amir H., Journal of the American Chemical Society, 2009, vol. 131, p. 3160 - 3161
  作者：Lee, Yunmi、Hoveyda, Amir H.

  DOI：——

  日期：——