methyl (1S,2R)-(-)-1-N-tert-butoxycarbonylamino-2-ethylcyclopropanecarboxylate | 167074-11-5

• 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-ethylcyclopropanecarboxylate
• 英文别名: (-)-methyl (1S,2R)-1-(N-tert-butoxycarbonylamino)-2-ethylcyclopropane-1-carboxylate；(1S,2R)-1-Boc-amino-2-ethylcyclopropylcarboxylic acid methyl ester；methyl (1S,2R)-2-ethyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylate
• CAS: 167074-11-5
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: HNHXMPOAAQHGMY-PELKAZGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R)-(-)-1-N-tert-butoxycarbonylamino-2-ethylcyclopropanecarboxylate 在 盐酸 、 甲醇 、 sodium hydroxide 作用下， 生成 (1S,2R)-1-氨基-2-乙基环丙烷羧酸
  参考文献：
  名称：

  Toshima, Hiroaki; Ochihara, Akitami, Bioscience, Biotechnology and Biochemistry, 1995, vol. 59, # 3, p. 497 - 500

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (3R,4R,4'S)-(-)-3-N-benzyloxycarbonylamino-4-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-pyrazoline-3-carboxylate 在 palladium dihydroxide 1,3-二甲基-2-苯基-2-磷杂咪唑烷 、 盐酸 、 甲醇 、 二苯甲酮 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -78.0~40.0 ℃ 、101.33 kPa 条件下， 反应 33.3h， 生成 methyl (1S,2R)-(-)-1-N-tert-butoxycarbonylamino-2-ethylcyclopropanecarboxylate
  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

• ——
  作者：Markus Kordes、Harald Winsel、Armin de Meijere

  DOI：10.1002/1099-0690(200009)2000:18<3235::aid-ejoc3235>3.0.co;2-7

  日期：2000.9

  Our recently reported titanium-mediated transformation of N,N-dialkylcarboxamides to cyclopropylamines has been applied to N,N-dibenzyl-2-benzyloxyacetamide using a variety of alkylmagnesium bromides to yield 1-(benzyloxymethyl)-1-(dibenzylamino)cyclopropane (15a, 48%) and 2-substituted analogs 15b−f (33−48%). These have been transformed in just a few steps into N-Boc-protected methyl esters of 1-

  我们最近报道的钛介导的N，N-二烷基羧酰胺向环丙胺的转化已使用各种烷基溴化镁应用于N，N-二苄基-2-苄氧基乙酰胺，以生成1-（苄氧基甲基）-1-（二苄氨基）环丙烷（15a，48％）和2取代的类似物15b-f（33-48％）。这些已转化在短短步入Ñ 1-氨基环丙烷羧酸（-Boc保护的甲酯1整体，29％），coronamic酸（2，35％）和norcoronamic酸（21％），2,3-甲基谷氨酸（21g，19％）和2,3-甲基鸟氨酸（21l，占12％）。类似地，3,4-亚甲基- γ氨基丁酸（相应的衍生物26，23％）和4-螺环丙烷-γ丁内酰胺（32，44％）已被合成。
• Enzymatic resolution of 1-amino-2-vinylcyclopropyl caboxylic acid methyl ester
  申请人：Boehringer Ingelheim (Canada) Ltd.

  公开号：US06268207B1

  公开（公告）日：2001-07-31

  An enantiomeric-resolving process for obtaining (1R,2S)-1-amino-2-vinylcyclopropyl carboxylic acid methyl ester by use of an esterase, and especially Alcalase®, is disclosed.

  通过使用酯酶，特别是Alcalase®，揭示了一种用于获取(1R,2S)-1-氨基-2-乙烯基环丙基羧酸甲酯的对映体分离过程。
• Hepatitis C inhibitor peptides
  申请人：Boehringer Ingelheim (Canada) Ltd.

  公开号：US06767991B1

  公开（公告）日：2004-07-27

  Disclosed herein are hepatitis C viral protease inhibitors of formula (I): wherein a is 0 or 1; b is 0 or 1; Y is H or C1-6 alkyl; B is H, an acyl derivative or a sulfonyl derivative; R6, when present, is C1-6 alkyl substituted with carboxyl; R5, when present, is C1-6 alkyl optionally substituted with carboxyl; R4 is C1-10 alkyl, C3-7 cycloalkyl or C4-10 (alkylcycloalkyl); R3 is C1-10 alkyl optionally substituted with carboxyl, C3-7 cycloalkyl or C4-10 (alkylcycloalkyl); R2 is CH2—R20, NH—R20, O—R20 or S—R20; wherein R20 is a saturated or unsaturated C3-7 cycloalkyl or C4-10 (alkyl cycloalkyl) being optionally mono-, di- or tri-substituted with R21, or R20 is a C6 or C10aryl, C7-16 aralkyl, Het or (lower alkyl)-Het, all optionally mono-, di- or tri-substituted with R21, wherein R21 is as defined herein; R1 is C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl, all optionally substituted with halogen; and W is hydroxy or a N-substituted amino: or W taken together with the carbonyl group to which it is bonded represents an ester group, or a pharmaceutically acceptable salt thereof.

  本文披露了式（I）的丙型肝炎病毒蛋白酶抑制剂：其中a为0或1；b为0或1；Y为H或C1-6烷基；B为H，酰基衍生物或磺酰基衍生物；R6在存在时为带有羧基的C1-6烷基；R5在存在时为可选择地带有羧基的C1-6烷基；R4为C1-10烷基，C3-7环烷基或C4-10（烷基环烷基）；R3为可选择地带有羧基的C1-10烷基，C3-7环烷基或C4-10（烷基环烷基）；R2为CH2—R20，NH—R20，O—R20或S—R20；其中R20为饱和或不饱和的C3-7环烷基或C4-10（烷基环烷基），可选择地单取代、双取代或三取代R21，或R20为C6或C10芳基，C7-16芳基烷基，Het或（较低烷基）-Het，均可选择地单取代、双取代或三取代R21，其中R21如本文所定义；R1为C1-6烷基，C2-6烯基或C2-6炔基，均可选择地带卤素取代；W为羟基或N-取代氨基：或W与其结合的羰基一起表示酯基，或其药用盐。
• 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.
• Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs
  作者：JoséM. Jiménez、Joan Rifé、Rosa M. Ortuño

  DOI：10.1016/0957-4166(96)00038-9

  日期：1996.2

  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.