(S)-2,2-Dimethoxy-1-phenylethanol | 151766-29-9

• 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: (S)-2,2-Dimethoxy-1-phenylethanol
• 英文别名: (1S)-2,2-dimethoxy-1-phenylethanol
• CAS: 151766-29-9
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: UTYCDKABDFEIBH-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2,2-Dimethoxy-1-phenylethanol 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 (S)-1-(phenyl)-1,2,2-trimethoxyethane
  参考文献：
  名称：

  Enantiomerically pure α-methoxyaryl acetaldehydes as versatile precursors: a facile chemo-enzymatic methodology for their preparation

  摘要：

  A facile and efficient synthesis of optically active alpha-methoxyaryl acetic acids (up to 95% ee), alpha-methoxyaryl ethanols (up to 93% ee) and alpha-methoxyaryl acetonitriles (up to 93% ee) was achieved via Arthrobacter sp. lipase-catalyzed kinetic resolution of masked aldehydes as the key synthons, that is, alpha-hydroxyaryl acetaldehyde acetals. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.023
• 作为产物：
  描述：

  2,2-二甲氧基-1-苯基乙酮 在 (S,S)-trans-[FeCl(CO)-(PPh2CH2CH2NHCHPhCHPhNCHCH2PPh2)]BPh4 、 potassium tert-butylate 、 异丙醇 作用下， 反应 0.05h， 以90%的产率得到
  参考文献：
  名称：

  Noyori加氢催化剂的铁变体，用于酮的不对称转移加氢。

  摘要：

  我们报告了一种用于酮的不对称转移氢化的新型铁催化剂的设计。这类铁催化剂结合了Noyori氢化催化剂的结构特征（轴向手性2,2'-双（膦基）-1,1'-联萘片段和金属-配体双功能基序）和烯键（酰胺基）可以激活熨斗中心。在被8当量的叔丁醇钾激活后，（S A，R P，SS）-7a和（S A，R P，SS）-7b是在室温下在异丙醇中苯乙酮和α，β-不饱和醛转移氢化的活性但非对映选择性催化剂。（S A，R P，SS）-7a的苯乙酮还原反应最大翻转数为14480 。（S A，R P，RR）-7b'中的轴向手性2,2'-双（膦基）-1,1'-联萘基与碳中心手性胺-亚胺部分的立体化学的正确组合提供了用于制备手性醇的对映体选择性催化剂，具有中等至良好的收率和宽泛的官能团耐受性。

  DOI：

  10.1039/d0dt01204a

文献信息

• Enantioselective hydrogenation of α-keto acetals with cinchona modified Pt catalyst
  作者：Martin Studer、Stefan Burkhardt、Hans-Ulrich Blaser

  DOI：10.1039/a905113i

  日期：——

  The enantioselective hydrogenation of a variety of α-keto acetals to the corresponding α-hydroxy acetals with Pt catalysts modified with cinchonidine derivatives is described with ees up to 97% and high reaction rates, and the influence of the substrate structure, the modifier and the reaction conditions (catalyst, solvent, temperature, pressure, modifier concentration) was investigated in some detail.

  该论文描述了用辛可尼丁衍生物修饰的铂催化剂将多种δ-酮乙缩醛对映体选择性氢化为相应的δ-羟基乙缩醛的过程，ees 高达 97%，反应速率高，并详细研究了底物结构、改性剂和反应条件（催化剂、溶剂、温度、压力、改性剂浓度）的影响。
• Catalytic enantioselective reactions. Part 16. Oxazaborolidine-catalyzed asymmetric borane reduction of α-keto acetals
  作者：Byung Tae Cho、Yu Sung Chun

  DOI：10.1039/a903335a

  日期：——

  Asymmetric reductions of α-keto acetals using various oxazaborolidines and borane reagents as catalyst and the hydride source, respectively, were compared. The reduction catalyzed by Corey’s CBS reagents with N-phenylamine–borane reagents provided α-hydroxy acetals with very high enantioselectivities for most aromatic analogues.

  比较了分别使用各种恶唑硼烷和硼烷试剂作为催化剂和氢化物源的α-酮缩醛的不对称还原。Corey的CBS试剂与N-苯胺-硼烷试剂催化的还原反应为大多数芳香族类似物提供了非常高对映选择性的α-羟基缩醛。
• Microbial reduction of 2-keto acetals as a biocatalytic approach to the enantioselective synthesis of optically active 2-hydroxy acetals
  作者：Patrizia Ferraboschi、Enzo Santaniello、Marco Tingoli、Fabrizio Aragozzini、Francesco Molinari

  DOI：10.1016/s0957-4166(00)80434-6

  日期：1993.8

  The reduction of the 2-keto acetals 1a and 1b by means of different microorganisms constitutes the biocatalytic access to optically active (46 to 100% ee) 2-hydroxy acetals, (S)-2a or (R)- and (S)-2b, representative compounds of a class of synthetically useful chiral building blocks.
• Asymmetric reduction of α-keto acetals with potassium 9-O-(1,2-isopropylidene-5-deoxy-D-xylofuranosyl)-9-boratabicyclo[3.3.1]nonane. Enantioselective synthesis of α-hydroxy acetals with high optical purities
  作者：Byung Tae Cho、Yu Sung Chun

  DOI：10.1016/0957-4166(94)80142-8

  日期：1994.7

  Asymmetric reduction of alpha-keto acetals with a chiral borohydride, potassiun 9-O-(1,2-isopropylidene-5-deoxy-alpha-D-xylofuranosyl)-9-boratabicyclo[3.3.1]nonane in THF at -78 degrees C provided the corresponding alpha-hydroxy acetals with 87-99% ee.
• Enantiomerically pure α-methoxyaryl acetaldehydes as versatile precursors: a facile chemo-enzymatic methodology for their preparation
  作者：Buddh Singh、Pankaj Gupta、Asha Chaubey、Rajinder Parshad、Shiromani Sharma、Subhash C. Taneja

  DOI：10.1016/j.tetasy.2008.10.023

  日期：2008.11

  A facile and efficient synthesis of optically active alpha-methoxyaryl acetic acids (up to 95% ee), alpha-methoxyaryl ethanols (up to 93% ee) and alpha-methoxyaryl acetonitriles (up to 93% ee) was achieved via Arthrobacter sp. lipase-catalyzed kinetic resolution of masked aldehydes as the key synthons, that is, alpha-hydroxyaryl acetaldehyde acetals. (C) 2008 Elsevier Ltd. All rights reserved.