[(2S)-1-亚硝基吡咯烷-2-基]甲醇 | 58246-54-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: [(2S)-1-亚硝基吡咯烷-2-基]甲醇
• 英文名称: 1-Nitroso-2(S)-pyrrolidinemethanol
• 英文别名: (S)-N-nitrosoprolinol；((2S)-1-Nitrosopyrrolidin-2-yl)methan-1-ol；[(2S)-1-nitrosopyrrolidin-2-yl]methanol
• CAS: 58246-54-1
• 化学式: C₅H₁₀N₂O₂
• 分子量: 130.147
• InChiKey: QZJDMCADRCEIQL-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2S)-1-亚硝基吡咯烷-2-基]甲醇 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到(2S)-1-氨基-2-吡咯甲醇
  参考文献：
  名称：

  向脯氨酸衍生的azo中添加有机铈：对映体富集胺的合成

  摘要：

  已经研究了将有机铈试剂（来自有机锂和有机镁前体）添加到由1-氨基脯氨酸衍生物制备的手性醛中。添加以高收率和高非对映选择性以及良好的亲核试剂（Me，n- Bu，i- Pr，t- Bu，Ph等）和底物范围（烷基，烯基和芳基）进行。生成的肼可通过氢解（阮内镍）的N–N键裂解或通过Li / NH 3的酰化和裂解而转化为胺。。通过改变取代基以包括更多的配位原子（氧和氮）以及去除配位原子，研究了侧链对非对映选择性的影响。带有2-甲氧基乙氧基甲基的SAMEMP助剂具有最高的非对映选择性。值得注意的是，带有简单甲基和异丁基取代基的助剂也具有很高的选择性。给出了选择性起源的假设。

  DOI：

  10.1016/j.tetasy.2010.04.042
• 作为产物：
  描述：

  L-脯氨醇 在 硫酸 、 silica gel 、 sodium nitrite 作用下， 生成 [(2S)-1-亚硝基吡咯烷-2-基]甲醇
  参考文献：
  名称：

  使用新的moiety部分作为立体导向剂的高度对映选择性，中等抗选择性醛醇缩合反应

  摘要：

  为了开发高度对映选择性，反非对映选择性的醛醇加成方法，已经研究了使用新型作为立体导向剂。产生了许多脯氨酸衍生的azo，并研究了它们在指导简单的氮杂-烯醇酸酯烷基化反应中的有效性。然后将这些promising中最有希望的用于醛醇缩合反应。脯氨酸的氧上的取代基对幅度和不对称感应感都具有深远的影响。戊酮与丙醛之间进行正式羟醛反应的最佳给出了37％的非对映选择性，有利于抗异构体，而两种异构体的ee均为83-84％。

  DOI：

  10.1016/j.tetasy.2005.09.027

文献信息

• Enantioselective synthesis of (R)-(−)-Cryptopleurine
  作者：Hideaki Suzuki、Sakae Aoyagi、Chihiro Kibayashi

  DOI：10.1016/0040-4039(94)02376-m

  日期：1995.2

  An enantioselective synthesis of naturally occurring (R)-(−)-cryptopleurine based on highly efficient asymmetric amidoalkylation using a cyclic N-acyliminium intermediate is described.

  描述了基于高效的不对称酰胺基烷基化的天然（R）-（-）-隐氨氯林的对映选择性合成，其使用环状N-酰基亚胺中间体。
• Nitrosated and nitrosylated diuretic compounds, compositions and methods of use
  申请人：Garvey S. David

  公开号：US20050059655A1

  公开（公告）日：2005-03-17

  The invention describes novel nitrosated and/or nitrosylated diuretic compounds or pharmaceutically acceptable salts thereof, and novel compositions comprising at least one nitrosated and/or nitrosylated diuretic compound, and, optionally, at least one nitric oxide donor and/or at least one therapeutic agent. The invention also provides novel compositions and kits comprising at least one diuretic compound of the invention, that is optionally nitrosated and/or nitrosylated, and, optionally, at least one nitric oxide donor compound and/or at least one therapeutic agent. The invention also provides methods for (a) treating conditions resulting from excessive water and/or electrolyte retention; (b) treating cardiovascular diseases; (c) treating renovascular diseases; (d) treating diabetes; (e) treating diseases resulting from oxidative stress; (f) treating endothelial dysfunctions; (g) treating diseases caused by endothelial dysfunctions; (h) treating cirrhosis; (j) treating pre-eclampsia; (k) treating osteoporosis; and (l) treating nephropathy.

  本发明描述了新型的硝酸化和/或亚硝酸化利尿化合物或其药学上可接受的盐，并且描述了至少包含一种硝酸化和/或亚硝酸化利尿化合物的新型组合物，以及可选地，至少包含一种一氧化氮供体和/或至少一种治疗剂的新型组合物。本发明还提供了包含本发明中的至少一种利尿化合物的新型组合物和套装，该利尿化合物可选择硝酸化和/或亚硝酸化，可选地包含至少一种一氧化氮供体化合物和/或至少一种治疗剂。本发明还提供了治疗以下病症的方法：(a)治疗由过多水和/或电解质滞留引起的病症；(b)治疗心血管疾病；(c)治疗肾血管疾病；(d)治疗糖尿病；(e)治疗由氧化应激引起的疾病；(f)治疗内皮功能障碍；(g)治疗由内皮功能障碍引起的疾病；(h)治疗肝硬化；(j)治疗先兆子痫；(k)治疗骨质疏松症；以及(l)治疗肾病。
• Chiroptical properties of n-nitrosopyrrolidines and n-nitrosamino acids
  作者：William Gaffield、Robert E. Lundin、Larry K. Keeper

  DOI：10.1016/s0040-4020(01)97934-7

  日期：——
• Asymmetric Total Synthesis of (R)-(-)-Cryptopleurine and (R)-(-)-Julandine via Highly Enantioselective Amidoalkylations with N-Acylhydrazonium Salts
  作者：Hideaki Suzuki、Sakae Aoyagi、Chihiro Kibayashi

  DOI：10.1021/jo00124a025

  日期：1995.9

  The first enantioselective total syntheses of the phenanthroquinolizidine alkaloid(-)-cryptopleurine (1) and its seco base (-)-julandine [(R)-3] are described. The synthesis of(R)-3 allowed the 9aS configuration to be assigned to natural dextrorotatory julandine as shown by structure (S)-3. Both synthetic approaches are based on the high degree of 1,3-asymmetric induction achieved using an N-acylhydrazonium salt, which belongs to a new structural class of activated azomethines. Upon exposure of methoxy lactam 9, with a chiral 2-substituted pyrrolidine auxiliary, to BF3 . Et(2)O and a silyl enol ether the in situ generated N-acylhydrazonium intermediate 10 underwent asymmetric nucleophilic addition to give the (GR)-keto lactams 13 and 14 with complete diastereoselectivity. On the other hand, nucleophilic addition to the N-acylhydrazonium ion 25, with an acyclic chiral auxiliary, showed poor diastereoselectivity. From these results, the high degree of diastereoselection observed for the N-acylhydrazonium ion 10 can be rationalized in terms of the pyramidal stability of the trivalent nitrogen in the chiral pyrrolidine auxiliary. Removal of the chiral auxiliary from 13 and 14 was achieved by reductive N-N bond cleavage using BH3 . THF, affording (BS)-piperidine derivatives 15 and 31, respectively, which were transformed into quinolizidinones 30 and 35, respectively, via intramolecular aldol condensation. Reduction of 30 with alane provided (-)julandine [(R)-3]. In addition, 35 was converted to (-)-cryptopleurine (1) in two steps, by radical cyclization with Bu(3)SnH and AIBN, followed by LiAlH4 reduction.
• Rosling, Ari; Fueloep, Ferenc; Sillanpaeae, Reijo, Heterocycles, 1997, vol. 45, # 1, p. 95 - 106
  作者：Rosling, Ari、Fueloep, Ferenc、Sillanpaeae, Reijo、Mattinen, Jorma

  DOI：——

  日期：——