methyl (1S,2R)-(-)-1-N-tert-butoxycarbonylamino-2-hydroxymethylcyclopropanecarboxylate | 171598-18-8

• 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: methyl (1S,2R)-(-)-1-N-tert-butoxycarbonylamino-2-hydroxymethylcyclopropanecarboxylate
• 英文别名: methyl (1S,2R)-2-(hydroxymethyl)-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylate
• CAS: 171598-18-8
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: MUJSIXNZBARGQX-CPCISQLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  methyl (1S,2R)-(-)-1-N-tert-butoxycarbonylamino-2-hydroxymethylcyclopropanecarboxylate 在 盐酸 、 甲醇 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 43.0h， 生成 3-(4-乙酰基苯基)-1-甲基-1-亚硝基脲
  参考文献：
  名称：

  Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs

  摘要：

  The syntheses of (-)-allo-coronamic acid, (-)-allo-norcoronamic acid, (-)-(Z)-2, 3-methanohomoserine, (-)-(Z)-2, 3-methanomethionine, and (2S, 3R)-Cbz-cyclo-Asp-OMe have been achieved in 45-68% overall yields from suitable intermediates derived from homochiral aminopentenoates which were obtained, in bun, from D-glyceraldehyde. The key synthetic step involves the quantitative and highly diastereoselective cyclopropanation of such precursors. The factors dealing with the control of stereoselectivity are highlighted and the main features in sidechain functionalization to the respective target molecules are discussed.

  DOI：

  10.1016/0957-4166(96)00038-9
• 作为产物：
  描述：

  trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate 在 盐酸 、 甲醇 、 sodium tetrahydroborate 、 sodium periodate 、 二苯甲酮 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 7.46h， 生成 methyl (1S,2R)-(-)-1-N-tert-butoxycarbonylamino-2-hydroxymethylcyclopropanecarboxylate
  参考文献：
  名称：

  Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs

  摘要：

  The syntheses of (-)-allo-coronamic acid, (-)-allo-norcoronamic acid, (-)-(Z)-2, 3-methanohomoserine, (-)-(Z)-2, 3-methanomethionine, and (2S, 3R)-Cbz-cyclo-Asp-OMe have been achieved in 45-68% overall yields from suitable intermediates derived from homochiral aminopentenoates which were obtained, in bun, from D-glyceraldehyde. The key synthetic step involves the quantitative and highly diastereoselective cyclopropanation of such precursors. The factors dealing with the control of stereoselectivity are highlighted and the main features in sidechain functionalization to the respective target molecules are discussed.

  DOI：

  10.1016/0957-4166(96)00038-9

文献信息

• Enantioselective synthesis of cyclopropane aminoalcohols containing quaternary stereogenic centers
  作者：Joan Rifé、Rosa M. Ortuño

  DOI：10.1016/s0957-4166(99)00463-2

  日期：1999.10

  Some title compounds have been synthesized in enantiomerically pure form starting from d- or l-glyceraldehyde as chiral precursors. A new synthesis of (+)-(Z)-methanohomoserine, one of the key intermediates employed, is also described. The target molecules are densely functionalized. Thus, in addition to one or two hydroxyl groups on a side-chain, an amino group is attached to a quaternary carbon of

  从对-或1-甘油醛作为手性前体开始，已经以对映体纯的形式合成了一些标题化合物。还描述了一种新合成的（+）-（Z）-甲氨基高丝氨酸，它是所使用的关键中间体之一。靶分子被密集地官能化。因此，除了侧链上的一个或两个羟基之外，氨基还连接到环丙烷环的季碳上，并且该立体中心的第四取代基包含卤素原子，烷基或环氧基。具有醇，硫醚或酯的功能。这些化合物中的一些在合成新的环丙烷核苷中是有用的前体。
• Synthesis, Structural Studies, and Biological Evaluation of Some Purine Substituted 1-Aminocyclopropane-1-carboxylic Acids and 1-Amino-1-hydroxymethylcyclopropanes
  作者：Zoran Džolić、Vedran Krištafor、Mario Cetina、Ante Nagl、Antonija Hergold-Brundić、Draginja Mrvoš-Sermek、Thomas Burgemeister、Mira Grdiša、Neda Slade、Krešimir Pavelić、Jan Balzarini、Erik De Clercq、Mladen Mintas

  DOI：10.1081/ncn-120022029

  日期：2003.7.1

  purine derivatives of 1-aminocyclopropane-1-carboxylic acid (8 and 9) and 1-amino-1-hydroxymethylcyclopropane (12 and 13) with methylene spacer between the base and the cyclopropane ring were prepared by multistep synthetic route involving alkylation of adenine and 6-(N-pyrrolyl)purine with 2-hydroxymethyl-1-aminocyclopropane-1-carboxylic acid derivative 3 as a key reaction. All novel compounds were

  摘要 通过包括烷基化在内的多步合成路线，制备了碱基与环丙烷环之间带有亚甲基间隔基的 1-氨基环丙烷-1-羧酸（8 和 9）和 1-氨基-1-羟甲基环丙烷（12 和 13）的新型嘌呤衍生物。腺嘌呤和 6-(N-吡咯基)嘌呤与 2-羟甲基-1-氨基环丙烷-1-羧酸衍生物 3 作为关键反应。所有新化合物都是外消旋的。通过分析二维同核和异核中的化学位移、HH 耦合常数和连接性，从它们的 1H 和 13C NMR 谱中推断出 4-13 中嘌呤环的 N-9 取代和环丙烷环的 Z 构型相关谱。通过 X 射线结构分析获得了 1、4 和 5 立体结构的明确证明。在几种细胞系中对新化合物的细胞抑制和抗病毒活性进行了评估。1,2-氨基环丙烷醇 12 的 6-(N-吡咯基) 嘌呤衍生物对宫颈癌 (HeLa) 和人成纤维细胞 (WI-38) 细胞的增殖比其他类型的肿瘤细胞系表现出更显着的抑制活性。这些化合物均未显示
• Synthesis of Potential Inhibitors of Ethylene Biosynthesis: The diastereoisomers of 1-amino-2-bromocyclopropanecarboxylic acid
  作者：Lukas Wick、Christoph Tamm、Thomas Boller

  DOI：10.1002/hlca.19950780211

  日期：1995.3.22

  The preparation of the diastereoisomers of 1-amino-2-bromocyclopropanecarboxylic acid is described using the methyl (1RS, 5SR)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate 5 as starting material. The key step is the oxidation of 9 with subsequent radical introduction of bromine according to the Barton procedure. The 2-bromo-cyclopropanecarboxylates cis-11 and trans-11 were obtained as diastereoisomer

  描述了以（1RS，5SR）-2-氧代-3-氧杂双环[3.1.0]己烷-1-羧酸甲酯5为起始原料的1-氨基-2-溴环丙烷羧酸的非对映异构体的制备。关键步骤是根据Barton程序将9氧化并随后自由基引入溴。的2-溴-环丙烷羧酸酯顺- 11和反式- 11 1：如在以3:1的比例对映异构体混合物获得。它们被转化为顺式和反式酯12和酸13。
• Enantioselective total syntheses of (−)-allo-coronamic acid, (−)-(Z)-2,3-methanohomoserine, and (2S,3R)-Cbz-cyclo-Asp-OMe
  作者：JoséM. Jiménez、Joan Rifé、Rosa M. Ortuño

  DOI：10.1016/0957-4166(95)00234-g

  日期：1995.8

  The title amino acids have been synthesized in 45, 47, and 63% overall yields, respectively, from enantiopure aminopentenoates, easily available from D-glyceraldehyde as a source of chirality, following divergent pathways from similar diols as common key intermediate compounds.