tert-butyl-(2R)-2-[(oxoacetyl)oxy]propanoate | 214278-70-3

• 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-(2R)-2-[(oxoacetyl)oxy]propanoate
• 英文别名: tert-butyl (2R)-2-oxaldehydoyloxypropanoate
• CAS: 214278-70-3
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: IZYGJRMECCPWMJ-ZCFIWIBFSA-N

物化性质

• 沸点：
  258.8±42.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl-(2R)-2-[(oxoacetyl)oxy]propanoate 在 四氯化钛 、 臭氧 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.58h， 生成 (1R)-2-tert-butoxy-1-methyl-2-oxoethyl (2R)-2-(5-chloro-2-iodoanilino)-4-oxobutanoate
  参考文献：
  名称：

  Novel Stereocontrolled Addition of Allylmetal Reagents to α-Imino Esters:  Efficient Synthesis of Chiral Tetrahydroquinoline Derivatives

  摘要：

  To prepare in multigram scale new antagonists of the glycine binding site associated to the NMDA receptor, an efficient distereoselective route was set up. The addition of suitable allyltin reagents to chiral N-aryl alpha-imino esters (R-(+)-tert-butyl lactate used as chiral auxiliary), gave the corresponding a amino acid-type derivative in high chemical yield and optical purity. This allylation reaction represents a novel example of efficient long-range stereodifferentiation process. In the last part of the synthesis, a regioselective Heck-type cyclization reaction enabled preparation of the target tetrasubstituted exocycle and trisubtituted endocycle double bond derivatives.

  DOI：

  10.1021/jo020327d
• 作为产物：
  描述：

  (+)-叔丁基 D-乳酸盐 在 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 tert-butyl-(2R)-2-[(oxoacetyl)oxy]propanoate
  参考文献：
  名称：

  Novel Stereocontrolled Addition of Allylmetal Reagents to α-Imino Esters:  Efficient Synthesis of Chiral Tetrahydroquinoline Derivatives

  摘要：

  To prepare in multigram scale new antagonists of the glycine binding site associated to the NMDA receptor, an efficient distereoselective route was set up. The addition of suitable allyltin reagents to chiral N-aryl alpha-imino esters (R-(+)-tert-butyl lactate used as chiral auxiliary), gave the corresponding a amino acid-type derivative in high chemical yield and optical purity. This allylation reaction represents a novel example of efficient long-range stereodifferentiation process. In the last part of the synthesis, a regioselective Heck-type cyclization reaction enabled preparation of the target tetrasubstituted exocycle and trisubtituted endocycle double bond derivatives.

  DOI：

  10.1021/jo020327d

文献信息

• Process Development and Scale Up of a Glycine Antagonist
  作者：Adam Banks、Gary F. Breen、Darren Caine、John S. Carey、Christopher Drake、Michael A. Forth、Asa Gladwin、Simone Guelfi、Jerome F. Hayes、Paolo Maragni、David O. Morgan、Paul Oxley、Alcide Perboni、Matthew E. Popkin、Fiona Rawlinson、Guillaume Roux

  DOI：10.1021/op9001824

  日期：2009.11.20

  A synthetic route amenable to large-scale synthesis of the glycine antagonist (2R,4E)-7-chloro-4-(2-oxo-1-phenyl-pyyrrolidin-3-ylidene)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid, (2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-penta-ol 12 is presented. The route consists of four stages of chemistry. Stage 1 starts from 5-chloro-2-iodoaniline hydrochloride and is a three-step telescoped stage consisting

  适用于大规模合成甘氨酸拮抗剂（2 R，4 E）-7-氯-4-（2-氧代-1-苯基-吡咯烷基-3-亚吡啶）-1,2,3,4的合成路线提出了-四氢喹啉-2-羧酸，（2 R，3 R，4 R，5 S）-6-（甲基氨基）己烷-1,2,3,4,5-戊醇12。该路线包括四个化学阶段。阶段1从5-氯-2-碘苯胺盐酸盐开始，是一个三步伸缩阶段，包括与乙二醛乙酯形成亚胺，使用乙烯基氧基三甲基硅烷进行曼尼希反应以及随后的与（2-氧代-1-苯基-3-的Wittig反应）吡咯烷基）三苯基溴化phosph。第一阶段产品（4 E）-2 [（（5-氯-2-碘代苯基）氨基] -4-（2-氧代-1-苯基-吡咯烷-3-亚叉基）丁酸乙酯17经过酶催化的动力学拆分以制备单（2 R）-对映体19作为乙酯。第3阶段是分子内Heck反应，得到（2 R，4 E）-7-氯-4-（2-氧代-1-苯基-吡咯烷烃-3-亚烷基）-1,2,3,4-四氢喹啉-2
• Tetrahydroquinoline derivatives as glycine antagonists
  申请人：——

  公开号：US20020052391A1

  公开（公告）日：2002-05-02

  1 Compounds of formula (I) or a salt, or metabolically labile ester thereof wherein R represents a group selected from halogen, alkyl, alkoxy, amino, alkylamino, dialkylamino, hydroxy, trifluoromethyl, trifluoromethoxy, nitro, cyano, SO 2 R 2 or COR 2 wherein R 2 represents hydroxy, methoxy, amino, alkylamino or dialkylamino; m is zero or an integer 1 or 2; R 1 represents a group (CH 2 ) n CN, —CH═CHR 3 , (CH 2 )nNHCOCH 2 R 4 or O(CH 2 )pNR 5 R 6 ; R 3 represents cyano or the group COR 7 ; R 4 represents alkoxy or a group NHCOR 8 ; R 5 and R 6 each represent independently hydrogen or alkyl, or R 5 and R 6 together with the nitrogen atom to which they are attached represent a heterocyclic group, or R 5 is hydrogen and R 6 is the group COR 9 ; R 7 represents an alkoxy, amino or hydroxyl group; R 8 represents a hydrogen atom or optionally substituted alkyl, alkoxy, aryl or heterocyclic group; R 9 is the group R 8 or the group NR 10 R 11 wherein R 10 represents hydrogen or alkyl group; R 11 represents optionally substituted alkyl, aryl, heterocyclic or cycloalkyl group; n is zero or an integer from 1 to 4; p is an integer from 2 to 4, processes for their preparation and to their use in medicine.

  化合物的公式(I)或其盐、代谢易变酯，其中R代表从卤素、烷基、烷氧基、氨基、烷基氨基、二烷基氨基、羟基、三氟甲基、三氟甲氧基、硝基、氰基、SO2R2或COR2中选择的基团，其中R2代表羟基、甲氧基、氨基、烷基氨基或二烷基氨基；m为零或整数1或2；R1代表(CH2)nCN、—CH═CHR3、(CH2)nNHCOCH2R4或O(CH2)pNR5R6中的基团；R3代表氰基或基团COR7；R4代表烷氧基或基团NHCOR8；R5和R6各自独立地代表氢或烷基，或R5和R6与它们连接的氮原子一起代表杂环基团，或R5是氢而R6是基团COR9；R7代表烷氧基、氨基或羟基；R8代表氢原子或可选地取代的烷基、烷氧基、芳基或杂环基团；R9是基团R8或基团NR10R11，其中R10代表氢或烷基团；R11代表可选地取代的烷基、芳基、杂环或环烷基团；n为零或1到4的整数；p为2到4的整数，以及它们的制备过程和在医药上的应用。
• TETRAHYDROQUINOLINE DERIVATIVES AS GLYCINE ANTAGONISTS
  申请人：GLAXO WELLCOME S.p.A.

  公开号：EP1086093A1

  公开（公告）日：2001-03-28
• US6362199B1
  申请人：——

  公开号：US6362199B1

  公开（公告）日：2002-03-26
• US6413985B1
  申请人：——

  公开号：US6413985B1

  公开（公告）日：2002-07-02