7,7-diphenyl-4,5,6,6a-tetrahydro-1H,3H-pyrrolo<1,2-c>oxazol-2-one | 160424-29-3

• 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: 7,7-diphenyl-4,5,6,6a-tetrahydro-1H,3H-pyrrolo<1,2-c>oxazol-2-one
• 英文别名: (5S)-<3.3.0>-1-aza-2-oxo-3-oxa-4,4-diphenyl-bicyclooctane；(S)-<3.3.0>-2-oxo-4,4-diphenyl-1-aza-3-oxabicyclooctane；(S)-[3.3.0]-1-aza-2-oxo-3-oxa-4,4-diphenylbicyclooctane；(5S)-1-aza-3-oxa-4,4-diphenylbicyclo[3.3.0]octan-2-one；1H,3H-Pyrrolo[1,2-c]oxazol-3-one, tetrahydro-1,1-diphenyl-, (7aS)-；(7aS)-1,1-diphenyl-5,6,7,7a-tetrahydropyrrolo[1,2-c][1,3]oxazol-3-one
• CAS: 160424-29-3
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: BEXXCWDIWBCVFX-INIZCTEOSA-N

物化性质

• 熔点：
  148-150 °C
• 沸点：
  485.0±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  7,7-diphenyl-4,5,6,6a-tetrahydro-1H,3H-pyrrolo<1,2-c>oxazol-2-one 在 palladium on activated charcoal lithium aluminium tetrahydride 、 亚硝酸特丁酯 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-methyleneamino-2-(diphenylmethyl)pyrrolidine
  参考文献：
  名称：

  三氟甲基化化合物的立体选择合成：甲醛N，N-二烷基hydr向三氟甲基酮的亲核加成。

  摘要：

  在没有任何催化剂或助催化剂的情况下，将甲醛N，N-二烷基hydr 1、2和7-10与三氟甲基酮3a-e进行亲核1,2-加成反应，得到一系列α-羟基-α-三氟甲基hydr （4、5和11-14）的优良率。从研究的几种试剂中，使用1-（亚甲基氨基）吡咯烷（2）合成外消旋加合物和（S）-1-（亚甲基氨基）-2- [1-（甲氧基）二苯基-甲基]-可获得最佳结果吡咯烷（10）为反应的不对称形式。由10携带的手性助剂的拆分特性使所获得的任何非对映异构体混合物易于色谱分离（快速）。因此，一次操作即可产生中等至良好数量（42-75％）的光学纯加合物（S，S）-14（de> / = 98％）结合了优异的化学产率（82-92％）和中等的光学产率（51-81％）。dra 5和（S，S）-14通过苄基化[-> 16和（S，S）-18]保护，然后通过MMPP氧化裂解转化为苄基保护的α-三氟甲基氰醇21和α-苄氧基-

  DOI：

  10.1021/jo991049u
• 作为产物：
  描述：

  Boc-L-脯氨酸甲酯 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 7,7-diphenyl-4,5,6,6a-tetrahydro-1H,3H-pyrrolo<1,2-c>oxazol-2-one
  参考文献：
  名称：

  Oxazaborolidines as Functional Monomers:  Ketone Reduction Using Polymer-Supported Corey, Bakshi, and Shibata Catalysts

  摘要：

  The first two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst have been prepared. Functional monomers based structurally upon the original B-methylated catalyst have been used to prepare catalytic polymers containing the CBS moiety bound both in a pendant fashion and in the form of a cross-link. Enantioselective reductions of two prochiral ketones have been carried out using the original catalyst in the solution phase as well as the two solid-state systems. While the pendant-bound system shows reduced stereoselectivity, the cross-linked version affords enantioselectivities almost identical to those of the solution-phase model.

  DOI：

  10.1021/jo026132n

文献信息

• Fluorinated Chiral Secondary Amines as Catalysts for Epoxidation of Olefins with Oxone
  作者：Chun-Yu Ho、Ying-Chun Chen、Man-Kin Wong、Dan Yang

  DOI：10.1021/jo048378t

  日期：2005.2.1

  amines having different substitution patterns and have screened them as catalysts for the asymmetric epoxidation of olefins using Oxone. The highest enantiomeric excess (61%) occurred for the epoxidation of 1-phenylcyclohexene catalyzed by a secondary amine bearing a fluorine atom at the β-position relative to the amino center. Our experimental results provide further support to the notion that the amine

  我们合成了一系列具有不同取代方式的手性环状仲胺，并筛选了它们作为使用Oxone进行烯烃不对称环氧化的催化剂。最高对映体过量（61％）是由相对于氨基中心在β位带有氟原子的仲胺催化的1-苯基环己烯的环氧化。我们的实验结果为以下观点提供了进一步的支持：胺在这些环氧化反应中起相转移催化剂和Oxone活化剂的双重作用。我们在这项工作中采用的微酸性反应条件避免了预先形成铵盐的需要，铵盐是介导环氧化的实际催化剂。
• Carbon Dioxide as a Carbonylating Agent in the Synthesis of 2-Oxazolidinones, 2-Oxazinones, and Cyclic Ureas: Scope and Limitations
  作者：Jairo Paz、Carlos Pérez-Balado、Beatriz Iglesias、Luis Muñoz

  DOI：10.1021/jo100268n

  日期：2010.5.7

  Carbon dioxide can be used as a convenient carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas. The transient carbamate anion generated by treating a primary or secondary amine group in basic media can be activated with phosphorylating agents such as Diphenylphosphoryl azide (DPPA) and Diphenyl chlorophosphate (DPPCl) but also with other types of electrophiles such

  在2-恶唑烷酮，2-恶嗪酮和环状脲的合成中，二氧化碳可用作方便的羰基化剂。通过在碱性介质中处理伯胺或仲胺基团而生成的瞬态氨基甲酸酯阴离子可以用磷酸化剂（如二苯基磷酰叠氮化物（DPPA）和二苯基氯代磷酸酯（DPPC1））活化，也可以用其他类型的亲电试剂（如SOCl 2，TsCl或氯化铝。羟基将活化的氨基甲酸酯分子内捕获导致形成2-恶唑烷酮或2-恶嗪酮，产率高至优异。该方法已成功地用于从相应的二胺合成高达7元环的环状脲。
• Carbonylation with CO2 and Phosphorus Electrophiles: A Convenient Method for the Synthesis of 2-Oxazolidinones from 1,2-Amino Alcohols
  作者：Luis Muñoz、Jairo Paz、Carlos Pérez-Balado、Beatriz Iglesias

  DOI：10.1055/s-0028-1087531

  日期：2009.2

  2-Oxazolidinones were prepared in good yields from 1,2-amino alcohols and CO2 in the presence of tetramethyl­phenylguanidine (PhTMG) as a base and a variety of phosphorus electrophiles under mild conditions. This procedure is advantageous over previous methodologies and relies on a novel carbonylation procedure that utilizes nontoxic CO2 and phosphorus electrophiles.

  2-噁唑烷酮在四甲基苯基胍（PhTMG）作为碱和多种磷电亲体的温和条件下，从1,2-氨基醇和CO2中以良好的收率制备。该方法优于以往的工艺，依赖于一种新颖的羰基化程序，利用无毒的CO2和磷电亲体。
• A short synthesis of (S)-2-(diphenylmethyl)pyrrolidine, a chiral solvating agent for NMR analysis
  作者：David J. Bailey、David O'Hagan、Mustafa Tavasli

  DOI：10.1016/s0957-4166(96)00495-8

  日期：1997.1

  A three step synthesis of (S)-2(diphenylmethyl)pyrrolidine 4 is described which allows its preparation on a large scale. The C-2 symmetric diamines 5 and 6 have been prepared from 4 and are attractive as potential ligands for asymmetric transformations. Pyrrolidine 4 has been assessed as a chiral solvating agent for the NMR analysis of chiral compounds. It emerges as a good CSA for carboxylic acids and some secondary alcohols. (C) 1997, Elsevier Science Ltd. All rights reserved.
• Organocatalytic Enantioselective Synthesis of Nitrogen-Substituted Dihydropyran-2-ones, a Key Synthetic Intermediate of 1β-Methylcarbapenems
  作者：Shoji Kobayashi、Tatsuhiro Kinoshita、Hisatoshi Uehara、Tomoko Sudo、Ilhyong Ryu

  DOI：10.1021/ol901544q

  日期：2009.9.3

  Organocatalytic enantioselective cycloadditions providing nitrogen-substituted dihydropyran-2-ones were developed in two catalytic systems. The (3R,4R)-product was a versatile intermediate in the synthesis of 1 beta-methylcarbapenem antibiotics.