[1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol | 134513-04-5

• 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: [1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol
• 英文别名: (2R)-(+)-1-tosylpyrrolidyl-2-methylalcohol；(R)-(1-tosylpyrrolidin-2-yl)methanol；(2R)-1-tosyl-2-pyrrolidinyl methyl alcohol；[(2R)-1-(4-methylphenyl)sulfonylpyrrolidin-2-yl]methanol
• CAS: 134513-04-5
• 化学式: C₁₂H₁₇NO₃S
• mdl: MFCD22793655
• 分子量: 255.338
• InChiKey: ROHDMTXJNIUWBL-LLVKDONJSA-N

物化性质

• 沸点：
  416.3±47.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol 在 草酰氯 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 (1R,2S')-α-(pyrrolidin-2-yl)benzyl alcohol
  参考文献：
  名称：

  Highly Stereoselective Syntheses of Proline-Derived Vicinal Amino Alcohols through Grignard Addition onto N-Tosylprolinal

  摘要：

  A highly diastereoselective Grignard addition to N-tosyl-l-prolinal has been developed to deliver a variety of proline-derived vicinal amino alcohols in good to excellent yields with high diastereoselectivities. A similar selectivity was also obtained by using N-tosyl-d-prolinal. The methodology has been applied to the synthesis of medicinally important 3-hydroxy-2-phenylpiperidines.

  DOI：

  10.1055/s-0035-1560802
• 作为产物：
  描述：

  D-脯氨酸 在 lithium aluminium tetrahydride 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol
  参考文献：
  名称：

  Highly Stereoselective Syntheses of Proline-Derived Vicinal Amino Alcohols through Grignard Addition onto N-Tosylprolinal

  摘要：

  A highly diastereoselective Grignard addition to N-tosyl-l-prolinal has been developed to deliver a variety of proline-derived vicinal amino alcohols in good to excellent yields with high diastereoselectivities. A similar selectivity was also obtained by using N-tosyl-d-prolinal. The methodology has been applied to the synthesis of medicinally important 3-hydroxy-2-phenylpiperidines.

  DOI：

  10.1055/s-0035-1560802

文献信息

• COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES
  申请人：Van Goor Fredrick F.

  公开号：US20110098311A1

  公开（公告）日：2011-04-28

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及包含上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• Copper Catalyzed Enantioselective Intramolecular Aminooxygenation of Alkenes
  作者：Peter H. Fuller、Jin-Woo Kim、Sherry R. Chemler

  DOI：10.1021/ja806585m

  日期：2008.12.31

  methyleneoxy-functionalized dihydroindolines and pyrrolidines. Tetramethylaminopyridyl radical (TEMPO) serves as both the source of the oxygen and the stoichiometric oxidant. These reactions are catalyzed by copper(II) triflate, complexed with (4S,5R)-Bis-Phbox. The unprotected aminoalcohols can be obtained by sequential dissolving metal reductions of the N-S and O-N bonds.

  本文报道了铜催化的烯烃的对映选择性分子内氨基氧化。这是对映选择性分子内烯烃氨基氧化过程的第一份报告。N-Arylsulfonyl-2-allylanilines 和 4-pentenylarylsulfonamides 以高产率和良好的对映选择性环化，提供新的手性亚甲氧基官能化二氢二氢吲哚和吡咯烷。四甲基氨基吡啶基（TEMPO）既是氧源又是化学计量氧化剂。这些反应由与 (4S,5R)-Bis-Phbox 络合的三氟甲磺酸铜 (II) 催化。未保护的氨基醇可以通过连续溶解 NS 和 ON 键的金属还原来获得。
• Catalytic Asymmetric Intramolecular α-Alkylation of Aldehydes
  作者：Nicola Vignola、Benjamin List

  DOI：10.1021/ja0392566

  日期：2004.1.1

  The development of a general catalytic asymmetric aldehyde alpha-alkylation reaction constitutes a major challenge in organic synthesis. Here, we report the first and successful approach toward its solution: (S)-alpha-methyl proline catalyzes the intramolecular alkylation of various halo aldehydes to the corresponding formyl cyclopentanes, -cyclopropanes, or -pyrrolidines in excellent yields and enantioselectivities

  通用催化不对称醛α-烷基化反应的发展构成了有机合成中的主要挑战。在这里，我们报告了第一个成功的解决方法：(S)-α-甲基脯氨酸以优异的产率和对映选择性催化各种卤代醛分子内烷基化为相应的甲酰基环戊烷、-环丙烷或-吡咯烷。最显着的是，外消旋化、醛醇化或催化剂烷基化没有发生任何显着的程度，进一步说明了烯胺催化的能力、温和性和高度选择性。
• Biphenyl derivatives and drug composition
  申请人：Wakamoto Pharmaceutical Co., Ltd.

  公开号：US06225306B1

  公开（公告）日：2001-05-01

  A biphenyl derivative represented by the following general formula (1) and a pharmaceutically acceptable salt thereof: [In the formula (1), A represents a single bond, —CH2—, —CO—, —CS— or —SO2—; B represents a single bond or —CH2—; R1 represents a hydrogen atom, —OH, —NR11R12 (wherein R11 and R12 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), —OCOCH3, or a halogen atom; R2 represents a hydrogen atom or R1 and R2 form a group ═O together; R3 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; provided that in the formula, the absolute configuration of the position a may be either R or S]. The compound of the present invention has considerably high safety and efficacy and is useful as, in particular, a vasopressin receptor antagonist.

  由以下一般式（1）表示的联苯衍生物和其药学上可接受的盐：[在式（1）中，A代表单键，—CH2—，—CO—，—CS—或—SO2—；B代表单键或— —；R1代表氢原子，—OH，—NR11R12（其中R11和R12各自独立地代表一个氢原子或具有1至4个碳原子的烷基基团），—OCOCH3或卤素原子；R2代表氢原子或R1和R2共同形成一个羟基；R3代表氢原子或具有1至4个碳原子的烷基基团；在该式中，位置a的绝对构型可以是R或S]。本发明的化合物具有相当高的安全性和有效性，并且特别适用作为抗利尿激素受体拮抗剂。
• 1-sulfonyl pyrrolidine derivatives
  申请人：——

  公开号：US20020019424A1

  公开（公告）日：2002-02-14

  The present invention is a series of compounds that are derivatives of 1-sulfonyl-pyrrolidine and that demonstrate affinity towards metabotropic glutamate receptors. The invention further relates to medicaments containing these compounds and to a process for their preparation. The compounds possess affinity towards metabotropic glutamate receptors and are therefore useful in the treatment or prevention of acute and/or chronic neurological disorders.

  本发明是一系列1-磺酰基吡咯烷衍生物化合物，它们表现出亲和力，适用于代谢型谷氨酸受体。本发明还涉及含有这些化合物的药物和它们的制备方法。这些化合物具有代谢型谷氨酸受体的亲和力，因此适用于治疗或预防急性和/或慢性神经系统疾病。