tert-butyl N-[(1S)-1-[(1R,2S,4S,5S)-4-methoxy-3-oxabicyclo[3.1.0]hexan-2-yl]-2-phenylethyl]carbamate | 225218-80-4

• 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: tert-butyl N-[(1S)-1-[(1R,2S,4S,5S)-4-methoxy-3-oxabicyclo[3.1.0]hexan-2-yl]-2-phenylethyl]carbamate
• CAS: 225218-80-4
• 化学式: C₁₉H₂₇NO₄
• 分子量: 333.428
• InChiKey: ARDDQYPXNPLDKX-XAJHFOFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S)-1-[(1R,2S,4S,5S)-4-methoxy-3-oxabicyclo[3.1.0]hexan-2-yl]-2-phenylethyl]carbamate 在 chromium(VI) oxide 、 硫酸 、 三甲基铝 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 tert-butyl N-[(1S,2S)-1-hydroxy-1-[(1R,2S)-2-[methoxy(methyl)carbamoyl]cyclopropyl]-3-phenylpropan-2-yl]carbamate
  参考文献：
  名称：

  Stereoselective elaboration of side chain residues in cyclopropane-containing dipeptide isosteres

  摘要：

  A variety of alkyl, substituted alkyl, and aryl side chain residues in cyclopropane-containing dipeptide isosteres were introduced by the highly diastereoselective (dr greater than or equal to 20:1) additions of organolithium or Grignard reagents to N, N-dimethylhydrazone 6. The resulting hydrazines were transformed into the corresponding N-Boc-protected amines with little or no stereochemical erosion. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00397-4
• 作为产物：
  描述：

  benzyllithium 在 1.) RaNi sodium hydroxide 、 氢气 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 tert-butyl N-[(1S)-1-[(1R,2S,4S,5S)-4-methoxy-3-oxabicyclo[3.1.0]hexan-2-yl]-2-phenylethyl]carbamate
  参考文献：
  名称：

  Stereoselective elaboration of side chain residues in cyclopropane-containing dipeptide isosteres

  摘要：

  A variety of alkyl, substituted alkyl, and aryl side chain residues in cyclopropane-containing dipeptide isosteres were introduced by the highly diastereoselective (dr greater than or equal to 20:1) additions of organolithium or Grignard reagents to N, N-dimethylhydrazone 6. The resulting hydrazines were transformed into the corresponding N-Boc-protected amines with little or no stereochemical erosion. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00397-4

文献信息

• Stereoselective elaboration of side chain residues in cyclopropane-containing dipeptide isosteres
  作者：Stephen F. Martin、Roy K. Hom

  DOI：10.1016/s0040-4039(99)00397-4

  日期：1999.4

  A variety of alkyl, substituted alkyl, and aryl side chain residues in cyclopropane-containing dipeptide isosteres were introduced by the highly diastereoselective (dr greater than or equal to 20:1) additions of organolithium or Grignard reagents to N, N-dimethylhydrazone 6. The resulting hydrazines were transformed into the corresponding N-Boc-protected amines with little or no stereochemical erosion. (C) 1999 Elsevier Science Ltd. All rights reserved.