(3S-顺式)-(+)-四氢-3-异丙基-7a-苯基吡咯并[2,1-b]恶唑-5(6H)-酮 | 88670-16-0

• 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: (3S-顺式)-(+)-四氢-3-异丙基-7a-苯基吡咯并[2,1-b]恶唑-5(6H)-酮
• 中文别名: (3S-顺)-(+)-四氢-3-异丙基-7A-苯基吡咯并[2,1-B]唑-5(6H)-酮
• 英文名称: (3S,7aS)-3-isopropyl-7a-phenyl-5-oxo-2,3,5,6,7,7a-hexahydropyrrolo<2,1-b>oxazole
• 英文别名: (S)-(+)-3-isopropyl-7a-phenyltetrahydro-pyrrolo[2,1-b]oxazol-5(6H)-one；(3S,7aS)-7a-phenyl-3-propan-2-yl-2,3,6,7-tetrahydropyrrolo[2,1-b][1,3]oxazol-5-one
• CAS: 88670-16-0
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: USVVTHSUMLVZJC-HIFRSBDPSA-N

物化性质

• 熔点：
  56-58 °C(lit.)
• 沸点：
  391.4±31.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (3S-顺式)-(+)-四氢-3-异丙基-7a-苯基吡咯并[2,1-b]恶唑-5(6H)-酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (3S,6S,7aS)-6-ethyl-6-methyl-7a-phenyl-3-propan-2-yl-3,7-dihydro-2H-pyrrolo[2,1-b][1,3]oxazol-5-one
  参考文献：
  名称：

  季碳中心的不对称合成

  摘要：

  Les lactames bicycliques chiraux 派生 de l'oxa-4 aza-1 bicyclo [3.3.0]octanone-8 子前体 tres utiles de center carbones quaternairesgeneres avec une enantioselectivite elevee

  DOI：

  10.1021/ja00316a071
• 作为产物：
  描述：

  L-缬氨醇 、 3-苯丙烯溴酸酯 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以85%的产率得到(3S-顺式)-(+)-四氢-3-异丙基-7a-苯基吡咯并[2,1-b]恶唑-5(6H)-酮
  参考文献：
  名称：

  季碳中心的不对称合成

  摘要：

  Les lactames bicycliques chiraux 派生 de l'oxa-4 aza-1 bicyclo [3.3.0]octanone-8 子前体 tres utiles de center carbones quaternairesgeneres avec une enantioselectivite elevee

  DOI：

  10.1021/ja00316a071

文献信息

• Synthesis of chiral 4,4-disubstituted-dihydropyridazines
  作者：Paul T. Buonora、Qun Zhang、Jennifer Sawko、Larry J. Westrum

  DOI：10.1016/j.tetasy.2007.11.026

  日期：2008.1

  In this paper, a novel general route to the stereospecific synthesis of chiral dihydropyridazines relying on the stereospecific formation of 1,4-diones is presented. The chirality is provided through the application of bicyclic lactams to the synthesis of the required diones. Treatment of the diones with hydrazine produces the pyridazine targets. In this report, the synthesis of four chiral 6-phenyl-4

  在本文中，提出了一种新的一般路线，该路线依赖于1,4-二酮的立体定向形成，用于手性二氢哒嗪的立体定向合成。通过将双环内酰胺应用于所需的二酮的合成来提供手性。用肼处理二酮产生哒嗪靶。在该报告中，还介绍了四种手性6-苯基-4,4-二取代-1,4-二氢哒嗪的合成方法。
• Palladium-Catalyzed α-Arylation of Meyers’s Chiral Bicyclic Lactams and a Deprotonative Ring-Opening Sideline
  作者：Hsin-Lun Chiang、Wei-Ting Zhao、Yen-Ku Wu、Yi-An Chen、Yi-Ching Lin、Pei-Lin Chen

  DOI：10.1055/a-2258-3788

  日期：2024.6

  α-arylation reaction of Meyers’s chiral bicyclic lactams (MCBLs) under palladium catalysis, and a substrate-dependent post-transformation. When the bridgehead carbon of the MCBLs is substituted with a methyl or an ethyl group, the initial arylation product undergoes a further rearrangement reaction to give a conjugated framework. On the other hand, substrates bearing a bridgehead isopropyl or aryl group are

  描述了 Meyers 手性双环内酰胺 (MCBL) 在钯催化下的去质子 α-芳基化反应，以及底物依赖性后转化。当MCBL的桥头碳被甲基或乙基取代时，最初的芳基化产物经历进一步的重排反应，得到共轭骨架。另一方面，带有桥头异丙基或芳基的底物被转化成相应的外芳基化产物。初步研究表明，重排途径是通过去质子化促进的，并且不依赖于钯催化。除了机械兴趣之外，这项研究还展示了功能化内酰胺的模块化和发散合成。
• The asymmetric synthesis of 2,2-dialkyl carboxylic esters and 2,2-disubstituted dihydronaphthalenes
  作者：A. I. Meyers、Richard H. Wallace、Michael Harre、Robert Garland

  DOI：10.1021/jo00297a032

  日期：1990.5
• Single and Double Diastereoselection in Azomethine Ylide Cycloaddition Reactions with Unsaturated Chiral Bicyclic Lactams
  作者：Andrew H. Fray、A. I. Meyers

  DOI：10.1021/jo9600870

  日期：1996.1.1

  Double diastereoselectivity data were analyzed to provide insight into the structural features that influence pi-facial selectivity in 1,3-dipolar cycloadditions of chiral and achiral azomethine ylides to chiral, unsaturated bicyclic lactams. Three major steric contributions to the differences in stability (Delta Delta G(double dagger)) between competing cycloaddition transition states were identified. The first major set of steric interactions involve that between the dipoles and the substituents on the left hemisphere (R(2)) and concave faces of the bicyclic lactams. This effectively hindered both alpha- and beta-approaches in the nonextended transition states shown in Figure 1. The second major steric interaction was provided by the nonbonded interactions (i) between the R(1) angular substituent on the bicyclic lactam and the pi-system of the dipole as shown in Figures 3 and 4. This interaction was shown to be very significant, causing reversal in pi-facial attack of chiral and achiral dipoles when the angular substituent is changed from phenyl or methyl to hydrogen. The high diastereoselectivity observed now opens a route to highly substituted chiral, nonracemic pyrrolidines.
• Conversion of γ-bicyclic lactams to 4,5-dihydro-2H-pyridazin-3-ones
  作者：Yu Jin Lim、Mia Angela、Paul T. Buonora

  DOI：10.1016/j.tetlet.2003.08.071

  日期：2003.10

  Bicyclic lactams are uniquely suited as precursors for the synthesis of chiral substituted 4,5-dihydro-2H-pyridazinones. This paper describes the development of a method for the direct conversion of unsubstituted and 4-substituted gamma-bicyclic lactams to 4,5-dihydro-2H-pyridazin-3-ones and 2-phenyl-4,5-dihydro-2H-pyridazin-3-ones. (C) 2003 Elsevier Ltd. All rights reserved.