tert-butyl (2S,4S)-4-(hydroxymethyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hept-6-enoate | 528588-38-7

• 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: tert-butyl (2S,4S)-4-(hydroxymethyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hept-6-enoate
• CAS: 528588-38-7
• 化学式: C₁₇H₃₁NO₅
• 分子量: 329.437
• InChiKey: NACWUKYAGDLQDP-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,4S)-4-(hydroxymethyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hept-6-enoate 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 12.0h， 生成 ditert-butyl (2S,4S)-4-prop-2-enylpyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  Efficient and stereoselective synthesis of novel cis-4-substituted proline analogues

  摘要：

  A series of novel cis-4-substituted proline analogues were designed and synthesized. Highly stereoselective alkylations at the gamma-position of glutamic ester 2 were achieved, followed by reduction, mesylation, and cyclization to afford the title compounds 1 in good yields and high diastereoselectivity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02865-4
• 作为产物：
  描述：

  Boc-L-谷氨酸-1-叔丁酯 在 sodium tetrahydroborate 、 N,N'-二环己基碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 21.5h， 生成 tert-butyl (2S,4S)-4-(hydroxymethyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hept-6-enoate
  参考文献：
  名称：

  Efficient and stereoselective synthesis of novel cis-4-substituted proline analogues

  摘要：

  A series of novel cis-4-substituted proline analogues were designed and synthesized. Highly stereoselective alkylations at the gamma-position of glutamic ester 2 were achieved, followed by reduction, mesylation, and cyclization to afford the title compounds 1 in good yields and high diastereoselectivity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02865-4