3-羟基-3-苯基丙酸丁酯 | 20306-00-7

• 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-苯基丙酸丁酯
• 英文名称: n-butyl 3-hydroxy-3-phenylpropionate
• 英文别名: n-butyl 3-hydroxy-3-phenylpropanoate；butyl 3-hydroxy-3-phenylpropanoate
• CAS: 20306-00-7
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: TXJGYNFLJUSEJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  3-羟基-3-苯基丙酸丁酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 magnesium chloride 、 磷脂酶B 作用下， 以 二氯甲烷 、 异丙醚 、 水 为溶剂， 反应 24.0h， 生成 (3R) n-butyl β-hydroxy-β-phenyl propionate
  参考文献：
  名称：

  Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy-β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates

  摘要：

  A simple and convenient method was reported for the preparation of optically active beta-hydroxy-beta-arylpropionates, delta-hydroxy-delta-aryl-beta-oxo-pentanoates and their butyryl derivatives via CRL-catalyzed hydrolysis. The optically active products are potential precursors of some chiral pharmaceuticals and natural products. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.059
• 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-苯基丙酸丁酯
  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

• Asymmetric reduction of prochiral 3-aryl-3-oxoesters with lithium borohydride using N,N′-dibenzoylcystine as a chiral auxiliary
  作者：Kenso Soai、Takashi Yamanoi、Hitoshi Hikima、Hidekazu Oyamada

  DOI：10.1039/c39850000138

  日期：——

  Optically active 3-aryl-3-hydroxyesters of high enantiomeric excess (80–92% e.e.) are obtained by the reduction of 3-aryl-3-oxoesters with lithium borohydride which has been chirally modified with N,N′-dibenzoylcystine and t-butyl alcohol.

  高对映体过量（80-92％ee）的旋光3-芳基-3-羟基酯是通过用N，N'-二苯甲酰基胱氨酸和t手性修饰的硼氢化锂还原3-芳基-3-氧代酯获得的。丁醇。
• Padhi, Santosh Kumar; Chadha, Anju, Synlett, 2003, # 5, p. 639 - 642
  作者：Padhi, Santosh Kumar、Chadha, Anju

  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.
• Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy-β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates
  作者：Chengfu Xu、Chengye Yuan

  DOI：10.1016/j.tet.2004.12.059

  日期：2005.2

  A simple and convenient method was reported for the preparation of optically active beta-hydroxy-beta-arylpropionates, delta-hydroxy-delta-aryl-beta-oxo-pentanoates and their butyryl derivatives via CRL-catalyzed hydrolysis. The optically active products are potential precursors of some chiral pharmaceuticals and natural products. (C) 2005 Elsevier Ltd. All rights reserved.