dimethyl (S)-N-(9-phenyl-9H-fluoren-9-yl)aspartate | 120230-62-8

• 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: dimethyl (S)-N-(9-phenyl-9H-fluoren-9-yl)aspartate
• 英文别名: (S)-dimethyl N-(9-phenylfluoren-9-yl)aspartate；dimethyl N-(9-phenylfluoren-9-yl)-L-aspartate；dimethyl L-N-(9-phenylfluoren-9-yl)aspartate；dimethyl N-(9-phenylfluorenyl)-(S)-aspartate；dimethyl N-(9-phenylfluorenyl)-aspartate；(S)-dimethyl 2-(9-phenyl-9H-fluoren-9-ylamino)succinate；dimethyl (2S)-2-[(9-phenylfluoren-9-yl)amino]butanedioate
• CAS: 120230-62-8
• 化学式: C₂₅H₂₃NO₄
• 分子量: 401.462
• InChiKey: IHNLZAIWFYSXBP-QFIPXVFZSA-N

物化性质

• 沸点：
  554.8±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (S)-N-(9-phenyl-9H-fluoren-9-yl)aspartate 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 草酰氯 、 硫酸 、 氢溴酸 、 银 、 ammonium formate 、 氯化二乙基铝 、 双(三甲基硅烷基)氨基钾 、 N,N-二甲基甲酰胺 、 potassium bromide 、 copper(I) bromide 、 锌 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 66.75h， 生成 毛果芸香碱
  参考文献：
  名称：

  An effective chirospecific synthesis of (+)-pilocarpine from L-aspartic acid

  摘要：

  A short and efficient synthesis of (+)-pilocarpine (1) has been accomplished in 10 steps and 51 % overall yield from L-aspartic acid. The synthesis features a diastereoselective alkylation of a protected aspartic acid diester derivative and a selective hydrolysis of the alpha-methyl ester to give the corresponding amino acid. Subsequent replacement of the amino group with bromo, esterification, and a modified Reformatsky reaction with 1-methylimidazole-5-carboxaldehyde (8) afforded imidazole-substituted lactone 28. Details concerning this novel lactone synthesis are also described. Finally, hydrogenolysis of the lactone carbon-oxygen bond and selective reduction of the resulting monoester afforded pure (+)-pilocarpine (1).

  DOI：

  10.1021/jo00057a031
• 作为产物：
  描述：

  9-溴-9-苯基芴 、 L-天冬氨酸二甲酯盐酸盐 在 potassium phosphate 、 lead(II) nitrate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以93%的产率得到dimethyl (S)-N-(9-phenyl-9H-fluoren-9-yl)aspartate
  参考文献：
  名称：

  An efficient and practical total synthesis of (+)-vincamine from L-aspartic acid

  摘要：

  DOI：

  10.1021/jo00297a023

文献信息

• A stereodivergent chirospecific synthesis of (3R) and (3S) 3-hydroxyaspartates by hydroxylation of aspartate diester enolates
  作者：F.Javier Sardina、Manuel M. Paz、Eduardo Fernández-Megía、Richard F. de Boer、M.Pilar Alvarez

  DOI：10.1016/s0040-4039(00)61333-3

  日期：1992.8

  A chirospecific and stereodivergent synthesis of N-(9-phenylfluorenyl)-3-hydroxyaspartates by hydroxylation of aspartate enolates is described. The stereochemistry of the newly created chiral center is controlled by the nature of the enolate counterion and the ligand coordinating ability of the solvents.

  描述了通过天冬氨酸烯醇酸酯的羟基化来合成N-（9-苯基芴基）-3-羟基天冬氨酸的手性和立体发散的方法。新产生的手性中心的立体化学由烯醇盐抗衡离子的性质和溶剂的配体配位能力控制。
• Sulfonylaminovalerolactams and derivatives thereof as factor Xa inhibitors
  申请人：Han Wei

  公开号：US20050096309A1

  公开（公告）日：2005-05-05

  The present application describes sulfonylaminovalerolactams and derivatives thereof of Formula Ia-If: or pharmaceutically acceptable salt forms thereof, wherein ring G is a mono- or bicyclic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了Formula Ia-If的磺酰氨基戊内内酰胺及其衍生物，或其药用可接受的盐形式，其中环G为单环或双环碳环或杂环。本发明的化合物可用作胰蛋白酶样丝氨酸蛋白酶抑制剂，特别是因子Xa的抑制剂。
• Preparation of novel N-sulfonylated (S,S)-2,3-diaminosuccinate-type chiral auxiliaries and application to an asymmetric 1,3-dipolar cycloaddition reaction of nitrile oxides to allyl alcohol
  作者：Masakazu Serizawa、Yutaka Ukaji、Katsuhiko Inomata

  DOI：10.1016/j.tetasy.2006.11.031

  日期：2006.11

  Novel N-sulfonylated (S,S)-2,3-diaminosuccinate-type chiral auxiliaries, which have the tartaric acid-like framework with a sulfonamide group instead of a hydroxyl group, were synthesized from l-aspartic acid. The synthesized (S,S)-2,3-diaminosuccinate derivatives were applied to an asymmetric 1,3-dipolar cycloaddition reaction of nitrile oxides to allyl alcohol to afford the corresponding optically

  由L-天冬氨酸合成了新型的N-磺酰化（S，S）-2,3-二氨基琥珀酸酯型手性助剂，其具有酒石酸样骨架，并带有磺酰胺基而不是羟基。将合成的（S，S）-2,3-二氨基琥珀酸酯衍生物应用于腈类化合物与烯丙醇的不对称1,3-偶极环加成反应中，得到相应的旋光性2-异恶唑啉，对映选择性高达73％ ee。通过使用酒石酸二异丙酯作为手性助剂，对脸部的分化与之截然相反。
• Synthesis of aspartic acid derivatives useful for the preparation of misacylated transfer RNAs
  作者：Michiel Lodder、Curtis F Crasto、Andrei L Laikhter、Haoyun An、Tuncer Arslan、Vladimir A Karginov、Glenn F Short III、Sidney M Hecht

  DOI：10.1139/v99-246

  日期：2000.6.1

  Several derivatives of aspartic acid were protected on N^αas their NVOC derivatives, and on the side chain carboxylates as nitroveratryl esters. Following activation as the cyanomethyl esters, these fully protected aspartate derivatives were converted to the respective pdCpA esters. The protected aspartyl-pdCpA esters were then utilized as substrates for T4 RNA ligase in the presence of in vitro transcripts of tRNA lacking the pCpA dinucleotide normally found at the 3'-end. In this fashion, several misacylated tRNAs were prepared; following photolytic deprotection, these were employed successfully for incorporation into proteins at predetermined positions.Key words: aminoacylated nucleotides, amino acid protection, protein synthesis, tRNA activation.

  若干个天冬氨酸衍生物被保护在Nα的NVOC衍生物上，侧链羧酸则以硝基维拉特酯形式保护。这些完全保护的天冬氨酸衍生物在氰甲基酯激活后，被转化为相应的pdCpA酯。保护的天冬氨酰-pdCpA酯随后被用作T4 RNA连接酶的底物，在缺少3'-端pCpA二核苷酸的tRNA体外转录物的存在下进行反应。通过这种方式，准备了若干个错误酰化的tRNA；在光解保护后，这些tRNA成功地用于在预定位置合成蛋白质。关键词：氨酰化核苷酸、氨基酸保护、蛋白质合成、tRNA激活。
• SULFONYLAMINOVALEROLACTAMS AND DERIVATIVES THEREOF AS FACTOR XA INHIBITORS
  申请人：Han Wei

  公开号：US20070099922A1

  公开（公告）日：2007-05-03

  The present application describes sulfonylaminovalerolactams and derivatives thereof of Formula Ia-If: or pharmaceutically acceptable salt forms thereof, wherein ring G is a mono- or bicyclic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了式Ia-If的磺酰氨基戊内酰内酰胺及其衍生物或其药学上可接受的盐形式，其中环G是单环或双环碳环或杂环。本发明的化合物可用作胰蛋白酶样丝氨酸蛋白酶的抑制剂，特别是Xa因子的抑制剂。