(R)-2-acetoxy-1-phenoxy-3-chloropropane | 140924-05-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-2-acetoxy-1-phenoxy-3-chloropropane
• 英文别名: (R)-1-chloro-2-acetoxy-3-phenoxypropane；[(2R)-1-chloro-3-phenoxypropan-2-yl] acetate
• CAS: 140924-05-6
• 化学式: C₁₁H₁₃ClO₃
• 分子量: 228.675
• InChiKey: ATNZXDVQLPRBMK-NSHDSACASA-N

物化性质

• 沸点：
  327.3±22.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-氯-3-苯氧基丙烷-2-基乙酸酯 生成 (R)-2-acetoxy-1-phenoxy-3-chloropropane
  参考文献：
  名称：

  酶辅助制备对映体纯的β-肾上腺素能阻滞剂III。旋光氯醇衍生物及其转化

  摘要：

  两个对映体系列的光学活性氯代醇衍生物2a-m和3a-m是通过酶水解和由假单胞菌属物种的高度选择性脂肪酶催化的酰基转移反应制备的。。将得到的结构单元进一步转化为高对映体纯度的相应β-受体阻滞剂。

  DOI：

  10.1016/s0957-4166(00)80256-6

文献信息

• Ruthenium- and Enzyme-Catalyzed Dynamic Kinetic Resolution of Secondary Alcohols
  作者：B. Anders Persson、Anna L. E. Larsson、Mikaël Le Ray、Jan-E. Bäckvall

  DOI：10.1021/ja983819+

  日期：1999.3.1

  Enzymatic resolution of secondary alcohols under substrate racemizing conditions was studied using an immobilized lipase from Candida antarctica in the presence of a ruthenium catalyst. A specifically designed acyl donor, 4-chlorophenyl acetate, was found to be compatible with both catalysts and resulted in an efficient dynamic kinetic resolution. Studies of the reaction in different solvents showed

  在钌催化剂存在下，使用来自南极念珠菌的固定化脂肪酶研究了底物外消旋条件下仲醇的酶促拆分。发现专门设计的酰基供体 4-氯苯乙酸酯与两种催化剂均相容，并导致有效的动态动力学拆分。在不同溶剂中的反应研究表明，非极性溶剂的结果最好。通过该过程，各种外消旋仲醇转化为相应的对映异构纯乙酸酯，有效利用所有原材料。在大多数情况下，反应以 >99% ee 和良好的收率进行。
• Aminocyclopentadienyl Ruthenium Complexes as Racemization Catalysts for Dynamic Kinetic Resolution of Secondary Alcohols at Ambient Temperature
  作者：Jun Ho Choi、Yoon Kyung Choi、Yu Hwan Kim、Eun Sil Park、Eun Jung Kim、Mahn-Joo Kim、Jaiwook Park

  DOI：10.1021/jo0355799

  日期：2004.3.1

  tests in the racemization of (S)-4-phenyl-2-butanol showed that 7 is the most active catalyst, although the difference decreased in the DKR. Complex 4 was used in the DKR of various alcohols; at room temperature, not only simple alcohols but also functionalized ones such as allylic alcohols, alkynyl alcohols, diols, hydroxyl esters, and chlorohydrins were successfully transformed to chiral acetates. In

  Aminocyclopentadienyl钌复合物，其可以用作常温消旋催化剂与在动态动力学拆分仲醇的（DKR），脂肪酶是从环戊-2,4- dienimines合成的Ru 3（CO）12，和CHCl 3： [2,3,4,5-PH 4（η 5 -C 4 CNHR）]的Ru（CO）2 Cl（上4：R =我-Pr; 5：R = ñ -Pr; 6：R =吨-Bu ），[2,5-ME 2 -3,4--PH 2（η 5 -C 4 CNHR）]的Ru（CO）2 Cl（上7：R = i -Pr; 8：R = PH），和[2,3,4,5-PH 4（η 5 -C 4 CNHAr）]的Ru（CO）2 Cl（上9：Ar为p -NO 2 ç 6 ħ 4 ; 10： Ar ＝p- ClC 6 H 4；11：Ar ＝ Ph；12：Ar ＝p- OMeC 6 H 4；13：Ar ＝p- NMe 2 C 6 H 4）。外消旋
• Chemoenzymatic Dynamic Kinetic Resolution of β-Halo Alcohols. An Efficient Route to Chiral Epoxides
  作者：Oscar Pàmies、Jan-E. Bäckvall

  DOI：10.1021/jo026157m

  日期：2002.12.1

  Enzymatic resolution of beta-chloro alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution (conversion up to 99% and ee up to 97%). The efficiency of the DKR is dramatically reduced when beta-bromo alcohols are used. The presence of the bromo substituent causes decomposition of the ruthenium catalysts, which triggers the progressive deactivation

  β-氯醇的酶促拆分与钌催化的醇异构化相结合，成功实现了动态动力学拆分（转化率高达99％，ee高达97％）。当使用β-溴醇时，DKR的效率会大大降低。溴取代基的存在会导致钌催化剂分解，从而触发酶的逐步失活。该方法的合成效用已通过不同手性环氧化物的实际合成得到说明。
• Enzyme assisted preparation of enantiomerically pure β-adrenergic blockers II. Building blocks of high optical purity and their synthetic conversion
  作者：Ulrich Ader、Manfred.P. Schneider

  DOI：10.1016/s0957-4166(00)80191-3

  日期：1992.1

  Based on previous screening results a series of potential building blocks 2-4 for beta-adrenergic blockers were prepared both by enzymatic hydrolysis and acyltransfer and further transformed into the corresponding oxiranes and aminoalcohols of defined absolute configurations.
• Enzyme assisted preparation of enantiomerically pure β-adrenergic blockers III. Optically active chlorohydrin derivatives and their conversion
  作者：Ulrich Ader、Manfred P. Schneider

  DOI：10.1016/s0957-4166(00)80256-6

  日期：1992.4

  Optical active chlorohydrin derivatives 2a-m and 3a-m of both enantiomeric series were prepared via both enzymatic hydrolyses and acyltransfer reactions catalysed by a highly selective lipase from Pseudomonas sp.. The resulting building blocks were further transformed into the corresponding β-blockers of high enantiomeric purity.

  两个对映体系列的光学活性氯代醇衍生物2a-m和3a-m是通过酶水解和由假单胞菌属物种的高度选择性脂肪酶催化的酰基转移反应制备的。。将得到的结构单元进一步转化为高对映体纯度的相应β-受体阻滞剂。