(2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(4-methoxyphenyl)-<4,5>-dehydropyrrolidine | 169774-71-4

• 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: (2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(4-methoxyphenyl)-<4,5>-dehydropyrrolidine
• 英文别名: methyl (2S,3S)-1-benzoyl-4-(4-methoxyphenyl)-3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-2,3-dihydropyrrole-2-carboxylate
• CAS: 169774-71-4
• 化学式: C₂₆H₂₉NO₆
• 分子量: 451.519
• InChiKey: AAUHFZKXXSCWLX-REWPJTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(4-methoxyphenyl)-<4,5>-dehydropyrrolidine 在 盐酸 、 三乙基硅烷 、 Dowex 50W-X₈ (H⁺ form) 、 苯甲醚 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 、 三氟乙酸 为溶剂， 反应 44.0h， 生成 (2S,3S,4S)-3-methylenecarboxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  迈向通用的类胡萝卜素合成：建立C-4立体化学的两种方法

  摘要：

  苯甲酸内酯的氢解和酰胺还原反应被用于生成被保护的C-4芳基取代的类海因类似物，该类似物被去保护成其相应的游离氨基酸。获得了C-4 2-MeOPh-类似物的X射线晶体学数据。

  DOI：

  10.1016/s0040-4020(97)00191-9
• 作为产物：
  描述：

  反式-4-羟基-L-脯氨酸甲酯盐酸盐 在 四(三苯基膦)钯 N,N-二甲基丙烯基脲 、 ruthenium trichloride 、 sodium periodate 、 碳酸氢钠 、 sodium carbonate 、 potassium carbonate 、 溶剂黄146 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 四氯化碳 、 乙二醇二甲醚 、 水 、 乙腈 、 苯 为溶剂， 反应 64.5h， 生成 (2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(4-methoxyphenyl)-<4,5>-dehydropyrrolidine
  参考文献：
  名称：

  Towards a versatile synthesis of kainoids I: Introduction of the C-3 and C-4 substituents

  摘要：

  The first stages in the synthesis of acromelic acid analogues from trans-4-hydroxy-L-proline are described. An enamine alkylation was used to stereospecifically introduce the C-3 substituent, Grignard addition to a ketone or Pd(0) catalysed cross-coupling procedures adding C-4 aryl substituents for further manipulation. A number of versatile intermediates were generated. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00190-7

文献信息

• Stereocontrol in the synthesis of kainoids
  作者：Jack E Baldwin、Andrew M Fryer、Mark R Spyvee、Roger C Whitehead、Mark E Wood

  DOI：10.1016/0040-4039(96)01522-5

  日期：1996.9

  A stereoselective synthesis of acromelic acid analogues is described in which the cis-relative stereochemistry is established by a hydroxyl directed heterogeneous catalytic hydrogenation of an enamide.

  描述了丙烯醛酸类似物的立体选择性合成，其中顺式相对立体化学通过烯丙基酰胺的羟基定向的非均相催化氢化而建立。
• A Versatile Approach to Acromelic Acid Analogues
  作者：J Baldwin

  DOI：10.1016/00404-0399(50)0841y-

  日期：1995.7.3
• Towards a versatile synthesis of kainoids III: Efficient methods for control of C-4 stereochemistry
  作者：Jack E. Baldwin、Andrew M. Fryer、Mark R. Spyvee、Roger C. Whitehead、Mark E. Wood

  DOI：10.1016/s0040-4020(97)00192-0

  日期：1997.4

  Halo- and silenolactonisation methods were used to prepare benzylic lactones from enamide carboxylic acids. The lactones were subsequently cleaved with predominantly inversion of configuration at the benzylic centre to give protected acromelic analogues with the correct C-4 stereochemistry. Hydroxyl directed heterogeneous hydrogenation of related enamide carbinols gave total stereocontrol at C-4. (C) 1997 Elsevier Science Ltd.
• Towards a versatile synthesis of kainoids I: Introduction of the C-3 and C-4 substituents
  作者：Jack E. Baldwin、Samantha J. Bamford、Andrew M. Fryer、Martin P.W. Rudolph、Mark E. Wood

  DOI：10.1016/s0040-4020(97)00190-7

  日期：1997.4

  The first stages in the synthesis of acromelic acid analogues from trans-4-hydroxy-L-proline are described. An enamine alkylation was used to stereospecifically introduce the C-3 substituent, Grignard addition to a ketone or Pd(0) catalysed cross-coupling procedures adding C-4 aryl substituents for further manipulation. A number of versatile intermediates were generated. (C) 1997 Elsevier Science Ltd.
• Towards a versatile synthesis of kainoids II: Two methods for establishment of C-4 stereochemistry
  作者：Jack E. Baldwin、Samantha J. Bamford、Andrew M. Fryer、Martin P.W. Rudolph、Mark E. Wood

  DOI：10.1016/s0040-4020(97)00191-9

  日期：1997.4

  Benzylic lactone hydrogenolysis and enamide reduction were used to generate protected C-4 aryl substituted kainoid analogues which were deprotected to their corresponding free amino acids. X-ray crystographic data were obtained for the C-4 2-MeOPh- analogue.

  苯甲酸内酯的氢解和酰胺还原反应被用于生成被保护的C-4芳基取代的类海因类似物，该类似物被去保护成其相应的游离氨基酸。获得了C-4 2-MeOPh-类似物的X射线晶体学数据。