(R)-(1-苄基)庚基乙酸酯 | 159690-73-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (R)-(1-苄基)庚基乙酸酯
• 英文名称: (R)-(1-benzyl)heptyl acetate
• 英文别名: (R)-1-phenyloctan-2-yl acetate
• CAS: 159690-73-0
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: QUQJUIVDJGPDFV-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-(1-苄基)庚基乙酸酯 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 8.0h， 生成 (R)-3-acetoxynonanoic acid
  参考文献：
  名称：

  Application of microbial enantiofacially selective hydrolysis in natural product synthesis

  摘要：

  Pichinia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)3-hydroxy-12- methyltridecanoate. a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification which could remove the minor enantiomer as the corresponding acetate.

  DOI：

  10.1016/s0957-4166(00)86269-2
• 作为产物：
  描述：

  (R)-7-benzyloxacycloheptan-2-one 在 吡啶 、 sodium hydroxide 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 14.5h， 生成 (R)-(1-苄基)庚基乙酸酯
  参考文献：
  名称：

  Application of microbial enantiofacially selective hydrolysis in natural product synthesis

  摘要：

  Pichinia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)3-hydroxy-12- methyltridecanoate. a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification which could remove the minor enantiomer as the corresponding acetate.

  DOI：

  10.1016/s0957-4166(00)86269-2

文献信息

• Highly Stereoselective Synthesis and Hydrogenation of (<i>Z</i>)-1-Alkyl-2-arylvinyl Acetates: a Wide Scope Procedure for the Preparation of Chiral Homobenzylic Esters
  作者：Pedro J. González-Liste、Félix León、Inmaculada Arribas、Miguel Rubio、Sergio E. García-Garrido、Victorio Cadierno、Antonio Pizzano

  DOI：10.1021/acscatal.6b00282

  日期：2016.5.6

  asymmetric hydrogenation of enol esters 3 has been covered for the first time. Using rhodium catalysts based on chiral phosphine-phosphite ligands (P-OP), highly enantioselective hydrogenations (up to 99% ee) have been achieved for a wide range of substrates. Thus, the synthesis and enantioselective hydrogenation of 3 provides a convenient and versatile procedure for the synthesis of valuable chiral homobenzylic

  通过使用两种互补方法，报道了具有广泛范围的（Z）-1-烷基-2-芳基乙烯基乙酸酯3的合成。第一种方法是将立体定向金催化的乙酸加成乙酸到1-碘代炔烃中，然后进行Suzuki偶联。第二，通过甲基苄基酮的烯酸酯的O-酰化选择性地获得了作为Z异构体的1-甲基-2-芳基乙烯基底物。此外，烯醇酯3的不对称氢化第一次被覆盖。使用基于手性膦-亚磷酸酯配体（P-OP）的铑催化剂，已实现了对多种底物的高度对映选择性氢化（最高99％ee）。因此，合成和对映选择性氢化3提供了有价值的手性homobenzylic酯合成的便利和多用途的过程。
• Broad Scope Synthesis of Ester Precursors of Nonfunctionalized Chiral Alcohols Based on the Asymmetric Hydrogenation of α,β-Dialkyl-, α,β-Diaryl-, and α-Alkyl-β-aryl-vinyl Esters
  作者：Félix León、Pedro J. González-Liste、Sergio E. García-Garrido、Inmaculada Arribas、Miguel Rubio、Victorio Cadierno、Antonio Pizzano

  DOI：10.1021/acs.joc.7b00710

  日期：2017.6.2

  a high enantioselectivity in the hydrogenation of E/Z mixtures (ca. Z/E = 75:25) of α,β-dialkylvinyl substrates, while a dramatic decrease on enantioselectivity was observed in the case of α-methyl-β-anisylvinyl acetate (Z/E = 58:42). Complementary deuteration reactions are in accord with a highly enantioselective hydrogenation for both olefin isomers in the case of α,β-dialkylvinyl esters. In contrast

  已经研究了使用带有手性膦-亚磷酸酯配体（P-OP）的Rh催化剂催化三取代烯醇酯的不对称加氢反应。所涵盖的底物包括α，β-二烷基，α-烷基-β-芳基和α，β-二芳基乙烯基酯，相应的氢化产物是制备合成上相关的手性非官能化醇的合适前体。反应性的比较表明其降低顺序为：α，β-二烷基>α-烷基-β-芳基>α，β-二芳基。基于所使用的P-OP配体的高度模块化结构，催化剂筛选确定了对α，β-二烷基（95-99％ee）和几乎所有α-烷基-β-芳基底物（92-98％ee）的高度对映选择性催化剂），但α-环己基-β-苯基乙酸乙烯酯表现出低的对映选择性（47％ee）。最后，α，β-二芳基乙烯基底物显示出较低的对映选择性（79-92％ee）。此外，某些催化剂在加氢脱氢反应中具有很高的对映选择性。È / ž混合物（约ž / ë = 75:25）的α，β-dialkylvinyl基板，而在α甲基-β-anisylvi