1-((3R,5S,7aS)-3-Phenyl-hexahydro-pyrrolo[2,1-b]oxazol-5-yl)-1H-benzotriazole | 728005-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1-((3R,5S,7aS)-3-Phenyl-hexahydro-pyrrolo[2,1-b]oxazol-5-yl)-1H-benzotriazole
• 英文别名: (3R,5S,7aS)-5-(benzotriazol-1-yl)-3-phenyl-2,3,5,6,7,7a-hexahydropyrrolo[2,1-b][1,3]oxazole
• CAS: 728005-56-9
• 化学式: C₁₈H₁₈N₄O
• 分子量: 306.367
• InChiKey: WMDJEWDGKBLINT-BZSNNMDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-((3R,5S,7aS)-3-Phenyl-hexahydro-pyrrolo[2,1-b]oxazol-5-yl)-1H-benzotriazole 在 正丁基锂 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 ((3R,5S,7aS)-5-Ethyl-3-phenyl-hexahydro-pyrrolo[2,1-b]oxazol-5-yl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Self-reproduction of chirality on α-aminophosphonates: asymmetric synthesis of α-alkylated diethyl pyrrolidin-2-yl-phosphonate

  摘要：

  A simple method for the asymmetric synthesis of alpha-substituted diethyl pyrrolidin-2-yl-phosphonate is described. The chiral oxazolopyrrolidine phosphonate was alkylated diastereospecifically with an alkyl halide. The key intermediate is an alpha-phosphonate-stabilized carbanion that can be alkylated without loss of optical activity and a single enantiomer of product was formed exclusively in 10-80% yield. The configurational assignment of the products relied on H-1-H-1 NOESY analysis of the alkylated oxazolopyrrolidine phosphonates. This represents an unprecedented case of self-regeneration of stereocenters (SRS) of cyclic aminophosphonates. The enantiomerically pure alpha-aminophosphonate dietlhyl-(2S)-(2-methylpyrrolidin-2-yl)-phosphonate, a surrogate of 2-methyl proline, was obtained upon hydrogenolysis of the chiral auxiliary in 83% yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.009
• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 T406石油添加剂 、 D-苯甘氨醇 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 1-((3R,5S,7aS)-3-Phenyl-hexahydro-pyrrolo[2,1-b]oxazol-5-yl)-1H-benzotriazole
  参考文献：
  名称：

  Self-reproduction of chirality on α-aminophosphonates: asymmetric synthesis of α-alkylated diethyl pyrrolidin-2-yl-phosphonate

  摘要：

  A simple method for the asymmetric synthesis of alpha-substituted diethyl pyrrolidin-2-yl-phosphonate is described. The chiral oxazolopyrrolidine phosphonate was alkylated diastereospecifically with an alkyl halide. The key intermediate is an alpha-phosphonate-stabilized carbanion that can be alkylated without loss of optical activity and a single enantiomer of product was formed exclusively in 10-80% yield. The configurational assignment of the products relied on H-1-H-1 NOESY analysis of the alkylated oxazolopyrrolidine phosphonates. This represents an unprecedented case of self-regeneration of stereocenters (SRS) of cyclic aminophosphonates. The enantiomerically pure alpha-aminophosphonate dietlhyl-(2S)-(2-methylpyrrolidin-2-yl)-phosphonate, a surrogate of 2-methyl proline, was obtained upon hydrogenolysis of the chiral auxiliary in 83% yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.009

文献信息

• Aminophosphonates as organocatalysts in the direct asymmetric aldol reaction: towards syn selectivity in the presence of Lewis bases
  作者：Peter Dinér、Mohamed Amedjkouh

  DOI：10.1039/b605091c

  日期：——

  and their performance was evaluated as organocatalysts in the direct asymmetric aldol reaction. High enantioselectivities (up to 99% ee) were achieved for a range of substituted cyclohexanones and benzaldehydes. Several organic bases, such as DBU, DBN, and TMG, were used together with the alpha-aminophosphonates in the aldol reactions and were found to favor syn-selectivity.

  已经合成了手性α-氨基膦酸酯，并在直接不对称醛醇缩合反应中将其性能作为有机催化剂进行了评估。对于一系列取代的环己酮和苯甲醛，实现了高对映选择性（高达99％ee）。几种有机碱，例如DBU，DBN和TMG，与Aldol反应中的α-氨基膦酸酯一起使用，发现它们有利于顺式选择性。
• Pyrrolidine Analogues of Lobelane: Relationship of Affinity for the Dihydrotetrabenazine Binding Site with Function of the Vesicular Monoamine Transporter 2 (VMAT2)
  作者：Ashish P. Vartak、Justin R. Nickell、Jaturaporn Chagkutip、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1021/jm900770h

  日期：2009.12.10

  Ring size reduction of the central piperidine ring of lobelane yielded pyrrolidine analogues that showed marked inconsistencies in their ability to bind to the dihydrotetrabenazine (DTBZ) binding site on the vesicular mono-amine transporter-2 (VMAT2) and their ability to inhibit VMAT2 function. The structure-activity relationships indicate that structural modification within the pyrrolidine series resulted in analogues that interact with two different sites, i.e., the DTBZ binding site and all alternative site on VMAT2 to inhibit transporter function.
• Self-reproduction of chirality on α-aminophosphonates: asymmetric synthesis of α-alkylated diethyl pyrrolidin-2-yl-phosphonate
  作者：Mohamed Amedjkouh、Kristina Westerlund

  DOI：10.1016/j.tetlet.2004.04.009

  日期：2004.6

  A simple method for the asymmetric synthesis of alpha-substituted diethyl pyrrolidin-2-yl-phosphonate is described. The chiral oxazolopyrrolidine phosphonate was alkylated diastereospecifically with an alkyl halide. The key intermediate is an alpha-phosphonate-stabilized carbanion that can be alkylated without loss of optical activity and a single enantiomer of product was formed exclusively in 10-80% yield. The configurational assignment of the products relied on H-1-H-1 NOESY analysis of the alkylated oxazolopyrrolidine phosphonates. This represents an unprecedented case of self-regeneration of stereocenters (SRS) of cyclic aminophosphonates. The enantiomerically pure alpha-aminophosphonate dietlhyl-(2S)-(2-methylpyrrolidin-2-yl)-phosphonate, a surrogate of 2-methyl proline, was obtained upon hydrogenolysis of the chiral auxiliary in 83% yield. (C) 2004 Elsevier Ltd. All rights reserved.