(S)-benzyl 2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate | 123803-29-2

• 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: (S)-benzyl 2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate
• 英文别名: (S)-benzyl 2-((methylsulfonyloxy)methyl)yrrolidine-1-carboxylate；(S)-benzyl 2-(methylsulfonylmethyl)pyrrolidine-1-carboxylate；(S)-N-Cbz-2-mesyloxymethylpyrrolidine；1-(benzyloxycarbonyl)-(2S)-pyrrolidin-2-ylmethyl methanesulfonate；(S)-(1-benzyloxycarbonylpyrrolidin-2-yl)methyl methanesulfonate；benzyl (S)-2-methylsulfonyloxymethylpyrrolidine-1-carboxylate；benzyl (2S)-2-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate
• CAS: 123803-29-2
• 化学式: C₁₄H₁₉NO₅S
• 分子量: 313.375
• InChiKey: RIIJHQMEMCVGMQ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate 在 sodium hydroxide 、 sodium hydride 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 61.0h， 生成 methoxy-[[(2S)-1-phenylmethoxycarbonylpyrrolidin-2-yl]methyl]phosphinic acid
  参考文献：
  名称：

  Catalytic Antibodies in Synthesis:  Design and Synthesis of a Hapten for Application to the Preparation of a Scalemic Pyrrolidine Ring Synthon for Ptilomycalin A

  摘要：

  A catalytic antibody-based approach toward the synthesis of an optically active pyrrolidine ring synthon potentially useful for ptilomycalin A is described. Enantiomerically pure hapten 37 was designed and constructed with the eventual goal of generating antibodies for the enantioselective partial hydrolysis of a meso diester such as 44 into a monoacid 45. This transition state analog possesses a phosphonate group containing the requisite oxyanionic character of the tetrahedral intermediate for ester hydrolysis. A newly developed carbamate-based linker, which was found to be much more hydrolytically stable than the commonly used glutarate ester, was developed for coupling of the hapten to a carrier protein.

  DOI：

  10.1021/jo951469t
• 作为产物：
  描述：

  氯甲酸苄酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-benzyl 2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  功能化季烷基铵离子液体催化的不对称迈克尔加成

  摘要：

  合成了一些官能化的季烷基铵离子液体，并将其用作醛和酮与硝基烯烃的不对称迈克尔加成反应的有机催化剂。它们都表现出出色的对映选择性 (> 99% ee) 和非对映选择性 (> 99/1 d/r)。其中一种催化剂 (S)-N,N-二甲基-N-吡咯烷-2-基甲基)-2-甲基丙-1-溴化铵可以回收再利用，结果相似，发现三乙胺是一种有效的添加剂提高其催化活性。

  DOI：

  10.3184/174751912x13280326501363

文献信息

• Sulfone derivatives, process for their production and use thereof
  申请人：——

  公开号：US20030187023A1

  公开（公告）日：2003-10-02

  A compound represented by the formula: 1 wherein R is a cyclic hydrocarbon group, or the like; W is a bond, or the like; X is a divalent hydrocarbon group, or the like; Y and Z are each independently —N(R 6 )— or the like; ring A is a nitrogen-containing heterocyclic ring, or the like; R5 and R6 are independently hydrogen atom, a hydrocarbon group, or the like; Z′ is imidoyl group, or the like; a is 0, 1 or 2; and b is 0 or 1, or a salt thereof.

  一个由以下式表示的化合物： 其中R是一个环烃基团，或类似物；W是一个键，或类似物；X是一个二价碳氢基团，或类似物；Y和Z分别独立地为—N(R6)—或类似物；环A是一个含氮杂环环，或类似物；R5和R6独立地为氢原子、一个碳氢基团，或类似物；Z′是亚胺基团，或类似物；a为0、1或2；b为0或1，或其盐。
• Tricyclic pyrrole or pyrazole derivative
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US06245796B1

  公开（公告）日：2001-06-12

  A tricyclic pyrrole or pyrazole derivative represented by the following general formula (I), or a pharmaceutically acceptable salt thereof, which shows strong affinity and selectivity for the 5-HT2C receptor and is useful for the treatment of central nervous system diseases such as sexual disorders, eating disorders, anxiety, depression and sleeping disorders. (In the above formula, each symbol means as follows; Y ring: an unsaturated five-membered ring which may have 1 to 3 of one or more types of hetero atom(s) each selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom or an unsaturated six-membered ring having 1 or 2 nitrogen atom(s), X: a bond or a carbon atom, a double bond or a single bond, V: a nitrogen atom or a group represented by a formula CH, and A: a straight or branched lower alkylene group which may be substituted with a halogen atom or a cycloalkyl group).

  以下是通用公式（I）所代表的三环吡咯或吡唑衍生物，或其药学上可接受的盐，该衍生物对5-HT2C受体具有强亲和力和选择性，并可用于治疗中枢神经系统疾病，如性功能障碍、进食障碍、焦虑、抑郁和睡眠障碍。（在上述公式中，每个符号的含义如下：Y环：一种不饱和的五元环，可能含有1至3个来自氮原子、氧原子和硫原子中的一种或多种异原子，或含有1或2个氮原子的不饱和六元环，X：一种键或一个碳原子，双键或单键，V：一个氮原子或一个由CH公式表示的基团，A：一种直链或支链低碳烷基基团，可能被卤原子或环烷基基团取代）。
• Pyrrolidine-Based Chiral Quaternary Alkylammonium Ionic Liquids as Organocatalysts for Asymmetric Michael Additions
  作者：Ge Wang、Huichao Sun、Xiaohui Cao、Ligong Chen

  DOI：10.1007/s10562-011-0649-4

  日期：2011.9

  A series of chiral pyrrolidine-type quaternary alkylammonium ionic liquids were synthesized and served as efficient catalysts for asymmetric Michael additions of aldehydes and ketones to nitroolefins, and the corresponding adducts were obtained in excellent enantioselectivities (>99% ee) and diastereoselectivities (>99% dr) under solvent-free reaction conditions. Furthermore, the catalyst 7c could

  合成了一系列手性吡咯烷型季烷基铵离子液体，作为醛和酮与硝基烯烃不对称迈克尔加成反应的有效催化剂，得到了相应的加合物，具有优异的对映选择性（>99% ee）和非对映选择性（>99%） dr) 在无溶剂反应条件下。此外，催化剂 7c 可以以相似的产率和选择性回收用于下一轮反应。 图形摘要
• Chiral pyrrolidine quaternary derivatives as organocatalysts for asymmetric Michael additions
  作者：Huichao Sun、Ge Wang、Xilong Yan、Ligong Chen

  DOI：10.1007/s11164-011-0480-y

  日期：2012.9

  A series of chiral pyrrolidine quaternary derivatives were designed and synthesized. It was found that these derivatives are highly efficient organocatalysts for the asymmetric Michael addition reactions of aldehydes and ketones to nitroolefins with high yields (up to 96%), high enantioselectivities (up to 99% ee), and high diastereoselectivities (up to 97:3 dr). Furthermore, catalyst 7a could be recycled without remarkable loss of catalytic activity and stereoselectivity.

  一系列手性吡咯烷四级衍生物被设计和合成。研究发现，这些衍生物在醛和酮与亚硝烯的不对称迈克尔加成反应中表现出高效的有机催化活性，产率高达96%，对映选择性高达99% ee，非对映选择性高达97:3 dr。此外，催化剂7a可以重复使用，并且没有明显损失催化活性和立体选择性。
• Synthesis and application of ligands for the asymmetric addition of organolithium reagents to imines
  作者：Catrin A. Jones、Iwan G. Jones、Mushtaq Mulla、Michael North、Lucia Sartori

  DOI：10.1039/a702028g

  日期：——

  Amino acid derived ligands 4d,e are prepared from (S)-valine and (S)-proline respectively, and can be used as chiral ligands during the asymmetric addition of organolithium reagents to N-arylimines. Ligand 4e, which is prepared by two independent routes, is found to induce addition of organolithium reagents to the si-face of the imines, whilst ligand 4d in common with the previously reported catalysts

  氨基酸衍生的配体4d，e分别由（S）-缬氨酸和（S）-脯氨酸制备，并且可以在将有机锂试剂不对称地添加至N-芳基胺中的过程中用作手性配体。配体4e中，它是由两个独立的途径制备，则发现诱导除了有机锂试剂的给SI亚胺的面取向，而在共同配体4d中与先前报道的催化剂4a-c中诱导除了重新的面取向亚胺。