Methyl N-(diphenylmethyl)-D,L-tryptophanate | 132659-98-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl N-(diphenylmethyl)-D,L-tryptophanate
• 英文别名: methyl 2-(benzhydrylamino)-3-(1H-indol-3-yl)propanoate
• CAS: 132659-98-4；143998-52-1
• 化学式: C₂₅H₂₄N₂O₂
• 分子量: 384.478
• InChiKey: PWBZJMHLZBTURM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl N-(diphenylmethyl)-D,L-tryptophanate 在 palladium on activated charcoal ammonium formate 、 三氟乙酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 72.0h， 生成 (1R,3S)-methyl 1-cyclohexyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-3-carboxylate
  参考文献：
  名称：

  Mechanism driven trans stereospecificity in the Pictet-Spengler reaction. Stereospecific formation of trans-1,2,3-trisubstituted-tetrahydro β- carbolines by condensation of Nb-diphenylmethyl tryptophan isopropyl esters wtm aldehydes

  摘要：

  Stereoelectronic control in the Pictet-Spengler condensation of N(b)-alkylsubstituted tryptophan alkyl esters has been employed to promote 100% stereoselectivity in this process. The reaction of N(b)-diphenylmethyl tryptophan isopropyl ester 8 with acetaldehyde in benzene at reflux yielded the trans-diastereomer 10d to the complete exclusion of the corresponding cis isomer. This trans stereospecificity was also observed for butyraldehyde and cyclohexylcarboxaldehyde.

  DOI：

  10.1016/s0040-4039(00)61268-6
• 作为产物：
  描述：

  吲哚 在 sodium tetrahydroborate 、 二氯乙基铝 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 Methyl N-(diphenylmethyl)-D,L-tryptophanate
  参考文献：
  名称：

  Balsamini; Duranti; Salvatori, Il Farmaco, 1990, vol. 45, # 10, p. 1111 - 1117

  摘要：

  DOI：

文献信息

• BALSAMINI, CESARINO;DURANTI, ERMANNO;SALVATORI, AMERICO;SPADONI, GILBERTO, FARMACO, 45,(1990) N0, C. 1111-1117
  作者：BALSAMINI, CESARINO、DURANTI, ERMANNO、SALVATORI, AMERICO、SPADONI, GILBERTO

  DOI：——

  日期：——
• Balsamini; Duranti; Salvatori, Il Farmaco, 1990, vol. 45, # 10, p. 1111 - 1117
  作者：Balsamini、Duranti、Salvatori、Spadoni、Barone

  DOI：——

  日期：——
• Mechanism driven trans stereospecificity in the Pictet-Spengler reaction. Stereospecific formation of trans-1,2,3-trisubstituted-tetrahydro β- carbolines by condensation of Nb-diphenylmethyl tryptophan isopropyl esters wtm aldehydes
  作者：Kevin M. Czerwinski、Li Deng、James M. Cook

  DOI：10.1016/s0040-4039(00)61268-6

  日期：1992.8

  Stereoelectronic control in the Pictet-Spengler condensation of N(b)-alkylsubstituted tryptophan alkyl esters has been employed to promote 100% stereoselectivity in this process. The reaction of N(b)-diphenylmethyl tryptophan isopropyl ester 8 with acetaldehyde in benzene at reflux yielded the trans-diastereomer 10d to the complete exclusion of the corresponding cis isomer. This trans stereospecificity was also observed for butyraldehyde and cyclohexylcarboxaldehyde.