sodium acetamidocinnamate | 100350-85-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: sodium acetamidocinnamate
• 英文别名: sodium α-(acetylamino)cinnamate；sodium;N-[(Z)-1-carboxy-2-phenylethenyl]ethanimidate
• CAS: 100350-85-4
• 化学式: C₁₁H₁₀NO₃*Na
• 分子量: 227.195
• InChiKey: ZCWRGPJCVOZVQG-VEZAGKLZSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.08
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  69.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  sodium acetamidocinnamate 在 Ru(BINAP)(cymene) 氢气 作用下， 以 水 为溶剂， 60.0 ℃ 、2.76 MPa 条件下， 反应 92.0h， 生成 N-乙酰-D-苯丙氨酸 、 N-乙酰-L-苯丙氨酸
  参考文献：
  名称：

  Modified silica-heterogenised catalysts for use in aqueous enantioselective hydrogenations

  摘要：

  Modified mesoporous silicas have been prepared, homogeneous organometallic catalysts incorporated and the resulting heterogeneous systems used as catalysts in aqueous enantioselective hydrogenation reactions. A series of catalysts in which the organometallic species was incorporated during gel synthesis generally gave good conversions but low ee values which were usually less than 25%. Preformed silicas with a narrow range of pore size (26 and 37 Angstrom) and an amorphous silica (average pore size 68 Angstrom) were modified by external surface deactivation and/or derivatization of the internal surface for potential tethering of the catalytic species. In general, excellent conversions (80-100%) but modest enantioselectivities (40-50%) were obtained when using 37 and 68 Angstrom silicas, similar to those values obtained using unmodified silicas. Only low conversions were obtained using the modified 26 Angstrom silicas. Pore volume measurements suggest that this is due to very restricted access to the pores when the tether is present. The results indicate that for aqueous hydrogenation the van der Waals interactions of the catalyst with the porous matrix are sufficiently strong to retain the catalyst, thus allowing for its reuse. No major advantage then appears to be gained by the use of potential internal tethers. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00925-6
• 作为产物：
  描述：

  (Z)-4-亚苄基-2-甲基噁唑-5(4h)-酮 、 sodium hydroxide 生成 sodium acetamidocinnamate
  参考文献：
  名称：

  SUH, JUNGHUN;LEE, EUN;MYOUNG, YOUNG, CHAN;KIM, MINWOO;KIM, SOODAN, J. ORG. CHEM., 1985, 50, N 7, 977-980

  摘要：

  DOI：

文献信息

• Process for producing N-acylphenylalanines
  申请人：MITSUI TOATSU CHEMICALS, Inc.

  公开号：EP0161796A1

  公开（公告）日：1985-11-21

  An N-acyl-substituted or unsubstituted phenylalanine is prepared by hydrolyzing a 2-substituted-4-substituted or unsubstituted benzylidene-5-oxazolone with an alkali, adjusting the reaction system containing its hydrolysis product with acid to a pH of 5 - 9 and reducing the resultant reaction solution catalytically in the presence of a palladium or platinum reducing catalyst. The reduction is carried out continuously without isolating the alkaline hydrolysis product, i.e., a substituted or unsubstituted N-acylaminocinnamic acid from the reaction system. The catalyst can be recovered after completion of the reduction and used repeatedly without additional treatment and without any observed lowering in its catalytic activity. Accordingly, the reductions using the recovered catalyst may proceed at pratically the same rate as reductions using a fresh catalyst.

  一种 N-酰基取代或未取代的苯丙氨酸是通过以下方法制备的：用碱水解 2-取代-4-取代或未取代的亚苄基-5-恶唑酮，用酸将含有其水解产物的反应体系调节到 pH 值为 5 - 9，然后在钯或铂还原催化剂存在下催化还原所得到的反应溶液。还原反应是连续进行的，无需从反应体系中分离出碱性水解产物，即取代或未取代的 N-酰基氨基肉桂酸。 催化剂可在还原完成后回收并重复使用，无需额外处理，也不会降低其催化活性。因此，使用回收催化剂进行还原的速度与使用新催化剂进行还原的速度基本相同。
• Nagel, Ulrich; Kinzel, Elke, Chemische Berichte, 1986, vol. 119, # 5, p. 1731 - 1733
  作者：Nagel, Ulrich、Kinzel, Elke

  DOI：——

  日期：——
• US4612388A
  申请人：——

  公开号：US4612388A

  公开（公告）日：1986-09-16
• Modified silica-heterogenised catalysts for use in aqueous enantioselective hydrogenations
  作者：Jim Jamis、John R Anderson、Ron S Dickson、Eva M Campi、W.Roy Jackson

  DOI：10.1016/s0022-328x(00)00925-6

  日期：2001.5

  Modified mesoporous silicas have been prepared, homogeneous organometallic catalysts incorporated and the resulting heterogeneous systems used as catalysts in aqueous enantioselective hydrogenation reactions. A series of catalysts in which the organometallic species was incorporated during gel synthesis generally gave good conversions but low ee values which were usually less than 25%. Preformed silicas with a narrow range of pore size (26 and 37 Angstrom) and an amorphous silica (average pore size 68 Angstrom) were modified by external surface deactivation and/or derivatization of the internal surface for potential tethering of the catalytic species. In general, excellent conversions (80-100%) but modest enantioselectivities (40-50%) were obtained when using 37 and 68 Angstrom silicas, similar to those values obtained using unmodified silicas. Only low conversions were obtained using the modified 26 Angstrom silicas. Pore volume measurements suggest that this is due to very restricted access to the pores when the tether is present. The results indicate that for aqueous hydrogenation the van der Waals interactions of the catalyst with the porous matrix are sufficiently strong to retain the catalyst, thus allowing for its reuse. No major advantage then appears to be gained by the use of potential internal tethers. (C) 2001 Elsevier Science B.V. All rights reserved.
• SUH, JUNGHUN;LEE, EUN;MYOUNG, YOUNG, CHAN;KIM, MINWOO;KIM, SOODAN, J. ORG. CHEM., 1985, 50, N 7, 977-980
  作者：SUH, JUNGHUN、LEE, EUN、MYOUNG, YOUNG, CHAN、KIM, MINWOO、KIM, SOODAN

  DOI：——

  日期：——