3-羟基-3-苯基丙酸正丙酯 | 157430-32-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 中文名称: 3-羟基-3-苯基丙酸正丙酯
• 英文名称: n-propyl 3-hydroxy-3-phenylpropanoate
• 英文别名: n-propyl 3-hydroxy-3-phenylpropionate；Propyl 3-hydroxy-3-phenylpropanoate
• CAS: 157430-32-5
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: OYRVHVIORRBIOT-UHFFFAOYSA-N

物化性质

• 沸点：
  329.8±22.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-羟基-3-苯基丙酸正丙酯 在 immobilised Candida parapsilosis ATCC 7330 whole cells 作用下， 以 丙醇 、 水 为溶剂， 反应 6.0h， 生成 (R)-n-propyl 3-hydroxy-3-phenylpropanoate 、 (S)-n-propyl 3-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  Deracemisation of β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330: substrate specificity and mechanistic investigation

  摘要：

  Deracemisation of aryl substituted beta-hydroxy esters by immobilised whole cells of Candida parapsilosis ATCC 7330 gave > 99% ee and up to 75% yield of their corresponding (S)-enantiomers. Mechanistic investigation of the deracemisation reaction carried out using a deuterated substrate, ethyl 3-deutero-3-hydroxy-3-phenyl propanoate revealed that while the (S)-enantiomer remains unreacted the (R)enantiomer undergoes enantioselective oxidation to its corresponding ketoester, which on complementary enantiospecific reduction gives the (S)-enantiomer in high yield and % ee. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.045
• 作为产物：
  描述：

  (+)-乙基 (R)-3-羟基-3-苯丙酸盐 在 sodium tetrahydroborate 、 immobilised Candida parapsilosis ATCC 7330 whole cells 作用下， 以 乙醇 、 水 为溶剂， 生成 3-羟基-3-苯基丙酸正丙酯
  参考文献：
  名称：

  Deracemisation of β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330: substrate specificity and mechanistic investigation

  摘要：

  Deracemisation of aryl substituted beta-hydroxy esters by immobilised whole cells of Candida parapsilosis ATCC 7330 gave > 99% ee and up to 75% yield of their corresponding (S)-enantiomers. Mechanistic investigation of the deracemisation reaction carried out using a deuterated substrate, ethyl 3-deutero-3-hydroxy-3-phenyl propanoate revealed that while the (S)-enantiomer remains unreacted the (R)enantiomer undergoes enantioselective oxidation to its corresponding ketoester, which on complementary enantiospecific reduction gives the (S)-enantiomer in high yield and % ee. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.045

文献信息

• Metal versus silyl triflate catalysis in the Mukaiyama aldol addition reaction
  作者：Erick M. Carreira、Robert A. Singer

  DOI：10.1016/s0040-4039(00)73344-2

  日期：1994.6

  of the Mukaiyama aldol addition reaction employing benzaldehyde and hydrocinnamaldehyde along with a selection of Lewis acids including BF3•OEt3, LiClO4, Yb(OTf)3, Sn(OTf)2, and Zn(OTf)2 is presented. The results of experiments conducted with doubly-labeled silyl ketene acetals implicate a Lewis acidic silicon species and not the metals as the catalyst in the Mukaiyama aldol addition reaction.

  向山醛醇加成反应的采用沿着与选择路易斯的苯甲醛和氢化肉桂醛甲机理研究酸，包括BF 3 •OET 3，的LiClO 4，镱（OTF）3，锡（OTF）2和Zn（OTF）2被呈现。用双标记甲硅烷基乙烯酮缩醛进行的实验结果暗示了路易斯酸性硅物质，而不是在Mukaiyama aldol加成反应中作为催化剂的金属。
• Padhi, Santosh Kumar; Chadha, Anju, Synlett, 2003, # 5, p. 639 - 642
  作者：Padhi, Santosh Kumar、Chadha, Anju

  DOI：——

  日期：——
• Carreira Erick M., Singer Robert A., Tetrahedron Lett, 35 (1994) N 25, S 4323-4326
  作者：Carreira Erick M., Singer Robert A.

  DOI：——

  日期：——
• Deracemisation of β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330: substrate specificity and mechanistic investigation
  作者：Santosh Kumar Padhi、D. Titu、N. Ganesh Pandian、Anju Chadha

  DOI：10.1016/j.tet.2006.03.045

  日期：2006.5

  Deracemisation of aryl substituted beta-hydroxy esters by immobilised whole cells of Candida parapsilosis ATCC 7330 gave > 99% ee and up to 75% yield of their corresponding (S)-enantiomers. Mechanistic investigation of the deracemisation reaction carried out using a deuterated substrate, ethyl 3-deutero-3-hydroxy-3-phenyl propanoate revealed that while the (S)-enantiomer remains unreacted the (R)enantiomer undergoes enantioselective oxidation to its corresponding ketoester, which on complementary enantiospecific reduction gives the (S)-enantiomer in high yield and % ee. (c) 2006 Elsevier Ltd. All rights reserved.