(1R,2S)-1-[(1R)-1-(benzyloxycarbonylamino)-2-propenyl]-2-hydroxymethylcyclopropane | 1338719-60-0

• 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: (1R,2S)-1-[(1R)-1-(benzyloxycarbonylamino)-2-propenyl]-2-hydroxymethylcyclopropane
• CAS: 1338719-60-0
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: XLNBPBOGZMCTTJ-MGPQQGTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,2S)-1-[(1R)-1-(benzyloxycarbonylamino)-2-propenyl]-2-hydroxymethylcyclopropane 、 N,N-双(苄氧基羰基)胍 在 potassium permanganate 、 sodium periodate 、 偶氮二甲酸二异丙酯 、 水 、 碳酸氢钠 、 三苯基膦 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 4.0h， 生成 (3R,4S)-3,4-methano-Nα,Nδ,Nω-tri-Cbz-L-arginine
  参考文献：
  名称：

  Synthesis of a series of 3,4-methanoarginines as side-chain conformationally restricted analogues of arginine

  摘要：

  A series of optically active stereoisomers of 3,4-methanoarginine (1-4 and ent-1-ent-4) with trans/cis, D/L, and syn/anti stereochemical diversity, the side-chains of which were restricted in various special arrangements, was designed as biologically useful arginine mimetics. These conformationally restricted arginine analogues were synthesized effectively by using a series of chiral 3,4-methanoamino acid equivalents (7-10 and ent-7-ent-10) as the key synthetic units. Their biological evaluation with three isoforms of nitric oxide synthase showed that trans-3,4-methano-L-syn-arginine (2) was a good substrate, having close potency to L-arginine, and isoforms selectivities were also similar to those of L-arginine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.049
• 作为产物：
  描述：

  (1R,2S)-2-((tert-butyldiphenylsiloxy)methyl)-1-[(1R)-1-((S)-tert-butylsulfinylamino)-2-propenyl]cyclopropane 在 盐酸 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 13.5h， 生成 (1R,2S)-1-[(1R)-1-(benzyloxycarbonylamino)-2-propenyl]-2-hydroxymethylcyclopropane
  参考文献：
  名称：

  Synthesis of a series of 3,4-methanoarginines as side-chain conformationally restricted analogues of arginine

  摘要：

  A series of optically active stereoisomers of 3,4-methanoarginine (1-4 and ent-1-ent-4) with trans/cis, D/L, and syn/anti stereochemical diversity, the side-chains of which were restricted in various special arrangements, was designed as biologically useful arginine mimetics. These conformationally restricted arginine analogues were synthesized effectively by using a series of chiral 3,4-methanoamino acid equivalents (7-10 and ent-7-ent-10) as the key synthetic units. Their biological evaluation with three isoforms of nitric oxide synthase showed that trans-3,4-methano-L-syn-arginine (2) was a good substrate, having close potency to L-arginine, and isoforms selectivities were also similar to those of L-arginine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.049