(6S,7Z)-7-hexylidene-5,5-dimethyl-3-oxa-1-azabicyclo[4.1.0]heptan-2-one | 1426587-42-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂卓类
• 英文名称: (6S,7Z)-7-hexylidene-5,5-dimethyl-3-oxa-1-azabicyclo[4.1.0]heptan-2-one
• CAS: 1426587-42-9
• 化学式: C₁₃H₂₁NO₂
• 分子量: 223.315
• InChiKey: KKCPQGWOMFXFLV-CHDRKKSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6S,7Z)-7-hexylidene-5,5-dimethyl-3-oxa-1-azabicyclo[4.1.0]heptan-2-one 、 chloroamine-T 在 potassium osmate(VI) dihydrate 、 苄基三乙基氯化铵 、 水 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以61%的产率得到N-[(2R)-1-[(4S)-5,5-dimethyl-2-oxo-1,3-oxazinan-4-yl]-1-oxoheptan-2-yl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  双环亚甲基-氮丙啶的氨基羟基化立体控制合成 1,3-二氨基-2-醇

  摘要：

  含氮立体三联体被定义为具有三个相邻立体定义碳原子的化合物，是几种生物相关化合物中的常见结构基序。1,3-二氨基-2-醇基序尤其是一种重要的药效团，其立体选择性合成方法有限。在这篇通讯中，我们描述了一系列双环亚甲基-氮丙啶的氨基羟基化，这些双环亚甲基-氮丙啶是通过一系列高烯基氨基甲酸酯的氮丙啶化反应获得的。这些有用的杂环支架的不寻常的电子和空间特征使得 Os 催化的环外烯烃的氨基羟基化具有高度的区域和立体选择性。建议的 N,O-氨基中间体重排为 1,3-二氨基-2-one，然后用 NaBH4 还原以提供所需的 1，

  DOI：

  10.1002/ejoc.201300416
• 作为产物：
  描述：

  在 [Rh2(O2CCPh3)4] 、 亚碘酰苯 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (6S,7E)-7-hexylidene-5,5-dimethyl-3-oxa-1-azabicyclo[4.1.0]heptan-2-one 、 (6S,7Z)-7-hexylidene-5,5-dimethyl-3-oxa-1-azabicyclo[4.1.0]heptan-2-one
  参考文献：
  名称：

  Chemoselective Allene Aziridination via Ag(I) Catalysis

  摘要：

  Allene aziridination generates useful bicyclic methylene aziridine scaffolds that can be flexibly transformed into a range of stereochemically complex and densely functionalized amine-containing stereotriads. The scope of this chemistry has been limited by the poor chemoselectivity that often results when typical dinuclear Rh(II) catalysts are employed with homoallenic carbamates. Herein, Ag(I) catalysts that significantly improve the scope and yield of bicyclic methylene aziridines that can be prepared via allene aziridination are described.

  DOI：

  10.1021/ol303167n

文献信息

• [EN] BICYCLIC METHYLENE AZIRIDINES AND REACTIONS THEREOF<br/>[FR] MÉTHYLÈNE AZIRIDINES BICYCLIQUES ET RÉACTIONS DE CELLES-CI
  申请人：SCHOMAKER JENNIFER

  公开号：WO2013033245A1

  公开（公告）日：2013-03-07

  The oxidative functionalization of olefins is a common method for the formation of vicinal carbon-heteroatom bonds. However, oxidative methods to transform allenes into synthetic motifs containing three contiguous carbon-heteroatom bonds are much less developed. The use of bicyclic methylene aziridines (MAs), prepared via intramolecular allene aziridination, as scaffolds for functionalization of all three allene carbons, among other reactions, is described herein.

  烯烃的氧化官能化是形成邻位碳-杂原子键的常见方法。然而，将联烯转化为含有三个相邻碳-杂原子键的合成基团的氧化方法发展得较少。本文描述了通过分子内联烯氮杂环化制备的双环亚甲基环氮烷（MAs）作为支架，用于官能化所有三个联烯碳原子，以及其他反应。
• BICYCLIC METHYLENE AZIRIDINES AND REACTIONS THEREOF
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20160075668A1

  公开（公告）日：2016-03-17

  The oxidative functionalization of olefins is a common method for the formation of vicinal carbon-heteroatom bonds. However, oxidative methods to transform allenes into synthetic motifs containing three contiguous carbon-heteroatom bonds are much less developed. The use of bicyclic methylene aziridines (MAs), prepared via intramolecular allene aziridination, as scaffolds for functionalization of all three allene carbons, among other reactions, is described herein.
• US9783512B2
  申请人：——

  公开号：US9783512B2

  公开（公告）日：2017-10-10
• Stereocontrolled Synthesis of 1,3-Diamino-2-ols by Aminohydroxylation of Bicyclic Methylene-Aziridines
  作者：Cale D. Weatherly、Ilia A. Guzei、Jennifer M. Schomaker

  DOI：10.1002/ejoc.201300416

  日期：2013.6

  bicyclic methylene-aziridines obtained from the aziridination of a series of homoallenic carbamates. The unusual electronic and steric features of these useful heterocyclic scaffolds render the Os-catalyzed aminohydroxylation of the exocyclic alkene highly regio- and stereoselective. Rearrangement of the proposed N,O-aminal intermediate to a 1,3-diamino-2-one is followed by reduction with NaBH4 to deliver

  含氮立体三联体被定义为具有三个相邻立体定义碳原子的化合物，是几种生物相关化合物中的常见结构基序。1,3-二氨基-2-醇基序尤其是一种重要的药效团，其立体选择性合成方法有限。在这篇通讯中，我们描述了一系列双环亚甲基-氮丙啶的氨基羟基化，这些双环亚甲基-氮丙啶是通过一系列高烯基氨基甲酸酯的氮丙啶化反应获得的。这些有用的杂环支架的不寻常的电子和空间特征使得 Os 催化的环外烯烃的氨基羟基化具有高度的区域和立体选择性。建议的 N,O-氨基中间体重排为 1,3-二氨基-2-one，然后用 NaBH4 还原以提供所需的 1，
• Chemoselective Allene Aziridination via Ag(I) Catalysis
  作者：Jared W. Rigoli、Cale D. Weatherly、Brian T. Vo、Samuel Neale、Alan R. Meis、Jennifer M. Schomaker

  DOI：10.1021/ol303167n

  日期：2013.1.18

  Allene aziridination generates useful bicyclic methylene aziridine scaffolds that can be flexibly transformed into a range of stereochemically complex and densely functionalized amine-containing stereotriads. The scope of this chemistry has been limited by the poor chemoselectivity that often results when typical dinuclear Rh(II) catalysts are employed with homoallenic carbamates. Herein, Ag(I) catalysts that significantly improve the scope and yield of bicyclic methylene aziridines that can be prepared via allene aziridination are described.