(R)-lactaldehyde diethyl acetal | 136616-74-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-lactaldehyde diethyl acetal
• 英文别名: (R)-1,1-diethoxy-2-propanol；(2R)-1,1-diethoxypropan-2-ol
• CAS: 136616-74-5
• 化学式: C₇H₁₆O₃
• 分子量: 148.202
• InChiKey: SWJACVWAJZRNFO-ZCFIWIBFSA-N

物化性质

• 沸点：
  203.3±20.0 °C(Predicted)
• 密度：
  0.955±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,1-二乙氧基丙酮 在 氢气 作用下， 以 正庚烷 、 溶剂黄146 、 甲苯 为溶剂， 30.0 ℃ 、5.0 MPa 条件下， 反应 24.0h， 以99%的产率得到
  参考文献：
  名称：

  高效和可回收的手性Pt纳米颗粒催化剂，用于活化酮的对映选择性加氢

  摘要：

  在制备用于制备手性α-羟基缩醛和手性1,2-二醇的活性酮的对映选择性加氢反应中，可调节温度的可分离相的手性Pt纳米颗粒催化剂表现出优异的ee（> 99％）。更重要的是，手性催化剂可以容易地通过相分离而分离，并且可以在下一个循环中直接重复使用，即使在克级反应中，也没有任何催化活性和对映选择性的损失。Pt的浸出量低于仪器的检测极限。

  DOI：

  10.1016/j.catcom.2018.03.012

文献信息

• Process for preparing optically active secondary alcohols having nitrogenous or oxygenic functional groups
  申请人：——

  公开号：US20030045727A1

  公开（公告）日：2003-03-06

  A process for preparing optically active secondary alcohols of the general formula (3), [wherein R 1 is linear lower alkyl, an aromatic ring group, or the like; A is CH 2 NR 2 R 3 or the like; n is an integer of 0 to 2; and * represents an asymmetric carbon atom] by asymmetrically hydrogenating a ketone compound of the general formula (1) having nitrogenous or oxygen functional group at any of the a-, &bgr;- and &ggr;-positions, with selectivity among functional groups by the use of a ruthenium/optically active bidentate phosphine/diamine complex as the catalyst in the presence of hydrogen alone or together with a base. The optically active secondary alcohols obtained by the process are useful as drugs and intermediates for the preparation of drugs.

  通过使用钌/光学活性双齿膦/二胺配合物作为催化剂，在存在氢气的情况下或与碱一起，通过不对称地氢化具有氮或氧官能团在α、β和γ位置中的酮化合物（1）来制备通式（3）的光学活性二级醇，[其中R1是线性低碳烷基、芳香环基等；A是CH2NR2R3或类似物；n是0到2的整数；*代表不对称碳原子]。通过该过程获得的光学活性二级醇可用作药物及药物中间体的制备。
• 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。
• Production of optically active &agr;-hydroxyacetals
  申请人：Solvias AG

  公开号：US06660890B1

  公开（公告）日：2003-12-09

  A process for the heterogeneous and enantioselective hydrogenation of prochiral organic &agr;-keto compounds with platinum as the catalyst in the presence of a soluble or immobilized chiral aromatic nitrogen base with at least one basic nitrogen atom adjacent to stereogenic carbon atoms, whereby prochiral &agr;-ketoacetals are hydrogenated to optically active &agr;-hydroxyacetals.

  一种利用铂作为催化剂，在可溶或固定的手性芳香族氮碱存在下，对非对映异构的有机α-酮化合物进行杂化和对映选择性氢化的过程，该手性芳香族氮碱至少具有一个邻近立体异构碳原子的碱性氮原子，从而将非对映异构的α-酮缩醛氢化为光学活性的α-羟基缩醛。
• PROCESS FOR PREPARING OPTICALLY ACTIVE SECONDARY ALCOHOLS HAVING NITROGENOUS OR OXYGENIC FUNCTIONAL GROUPS
  申请人：Asahi Kasei Kabushiki Kaisha

  公开号：EP1254885A1

  公开（公告）日：2002-11-06

  The present invention provides a process for the preparation of an optically active secondary alcohol represented by the general formula (3): wherein R1 represents a straight-chain lower alkyl group, an aromatic ring group, or the like; A represents CH2NR2R3, or the like; n is an integer of from 0 to 2; and * represents an asymmetric carbon atom, which comprises asymmetrically hydrogenating with selectivity among the functional groups, a ketone compound represented by the general formula (1) having a nitrogenous or oxygenic functional group at any of the α-, β- and γ-positions: wherein R1, A and n are as defined above, using a ruthenium/optically active bidentate phosphine/diamine complex as a catalyst in the presence of hydrogen or in the presence of hydrogen and a base. The optically active secondary alcohols obtained by the present process are useful as medicaments and intermediates for producing medicaments.

  本发明提供了一种由通式（3）表示的光学活性仲醇的制备方法： 其中 R1 代表直链低级烷基、芳香环基或类似基团；A 代表 CH2NR2R3 或类似基团；n 是 0 至 2 的整数；以及 * 代表不对称碳原子，其包括以官能团之间的选择性不对称氢化通式 (1) 所代表的酮化合物，该酮化合物在 α-、β- 和 γ- 位置上具有含氮或含氧官能团： 其中 R1、A 和 n 如上定义，使用钌/光学活性双齿膦/二胺络合物作为催化剂，在氢气存在下或在氢气和碱存在下进行。 通过本工艺获得的光学活性仲醇可用作药物和生产药物的中间体。
• Use of dihydroxyacetone phosphate-dependent aldolases in the synthesis of deoxy aza sugars
  作者：Kevin K. C. Liu、Tetsuya Kajimoto、Lihren Chen、Ziyang Zhong、Yoshitaka Ichikawa、Chi Huey Wong

  DOI：10.1021/jo00022a013

  日期：1991.10

  The use of fructose-1,6-diphosphate (FDP), fuculose-1-phosphate (Fuc-1-P) and rhamnulose-1-phosphate (Rham-1-P) aldolases in organic synthesis is described. Fuc-1-P, Rham-1-P, and their phosphate-free species have been prepared and characterized. Both Fuc-1-P and Rham-1-P aldolases accept 3-azido-2-hydroxypropanal as a substrate to form L-omega-azidoketose phosphates, which upon dephosphorylation and hydrogenolysis on Pd/C, gave 1-deoxyazasugars structurally related to D-galactose and L-mannose. Hydrogenolysis of the enzyme products azidoketose 1-phosphates, however, gave 1,6-dideoxyazasugars structurally related to 6-deoxygalactose and L-rhamnose. Explanations for the stereoselectivity in the hydrogenolysis reactions were provided. Similarly, FDP aldolase catalyzed the aldol condensation reaction with 2-azido-3-hydroxypropanal to afford a new synthesis of 2(R),5(S)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine, a potent inhibitor of a number of glycosidases. A new empirical formula is developed to relate the inhibition constants and inhibitor binding for alpha- and beta-glucosidases.