(1S,3S,5R,7R)-3,8,8-trimethyl-4-azatricyclo[5.1.0.0^3,5]octane | 1310689-05-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,3S,5R,7R)-3,8,8-trimethyl-4-azatricyclo[5.1.0.0^3,5]octane
• 英文别名: (1S,3S,5R,7R)-3,8,8-trimethyl-4-azatricyclo[5.1.0.03,5]octane
• CAS: 1310689-05-4
• 化学式: C₁₀H₁₇N
• 分子量: 151.252
• InChiKey: NKIWAQHGRBLVNS-JIOCBJNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,3S,5R,7R)-3,8,8-trimethyl-4-azatricyclo[5.1.0.0^3,5]octane 在 lithium aluminium tetrahydride 、 sodium azide 、 cerium(III) chloride heptahydrate 作用下， 以 甲基叔丁基醚 、 水 、 乙腈 为溶剂， 反应 1.92h， 生成 (1S,3S,4S,6R)-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diamine
  参考文献：
  名称：

  Synthesis of new enantiopure trans-3,4-diaminocaranes from (+)-3-carene

  摘要：

  A synthetic strategy to obtain new enantiopure trans-3,4-diaminocaranes derived from (+)-3-carene via a stereoselective methodology is described. The stereoselective preparation of 3,4-alpha-carene- or 3,4-beta-carene-epoxide is followed by a ring opening by sodium azide to obtain the azido-alcohols. Subsequent cyclization affords the corresponding aziridine diastereoisomers, which are converted to azido amines by opening of the aziridine rings by sodium azide and then reduced to the final diamine diastereoisomers. The absolute configurations of the final diamines and of novel intermediates are established by H-1 NMR spectra correlated with conformational analysis supported by molecular modeling. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.027
• 作为产物：
  描述：

  3,8,8-三甲基-4-氧杂三环[5.1.0.03,5]辛烷 在 sodium azide 、 氯化铵 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 50.0h， 生成 (1S,3S,5R,7R)-3,8,8-trimethyl-4-azatricyclo[5.1.0.0^3,5]octane
  参考文献：
  名称：

  Synthesis of new enantiopure trans-3,4-diaminocaranes from (+)-3-carene

  摘要：

  A synthetic strategy to obtain new enantiopure trans-3,4-diaminocaranes derived from (+)-3-carene via a stereoselective methodology is described. The stereoselective preparation of 3,4-alpha-carene- or 3,4-beta-carene-epoxide is followed by a ring opening by sodium azide to obtain the azido-alcohols. Subsequent cyclization affords the corresponding aziridine diastereoisomers, which are converted to azido amines by opening of the aziridine rings by sodium azide and then reduced to the final diamine diastereoisomers. The absolute configurations of the final diamines and of novel intermediates are established by H-1 NMR spectra correlated with conformational analysis supported by molecular modeling. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.027

文献信息

• Titanium and Cobalt Bimetallic Radical Redox Relay for the Isomerization of N-Bz Aziridines to Allylic Amides
  作者：Song Lin、Devin P. Wood、Weiyang Guan

  DOI：10.1055/s-0037-1610779

  日期：2021.11

  Herein a bimetallic radical redox-relay strategy is employed to generate alkyl radicals under mild conditions with titanium(III) catalysis and terminated via hydrogen atom transfer with cobalt(II) catalysis to enact base-free isomerizations of N-Bz aziridines to N-Bz allylic amides. This reaction provides an alternative strategy for the synthesis of allylic amides from alkenes via a three-step sequence

  本文采用双金属自由基氧化还原-中继策略，在钛(III)催化的温和条件下生成烷基自由基，并通过钴(II)催化的氢原子转移终止，以进行N -Bz氮丙啶到N -Bz的无碱异构化烯丙基酰胺。该反应提供了一种通过三步序列从烯烃合成烯丙基酰胺的替代策略，以完成正式的转位烯丙基胺化。
• Direct and Stereospecific Synthesis of <i>N</i> ‐H and <i>N</i> ‐Alkyl Aziridines from Unactivated Olefins Using Hydroxylamine‐ <i>O</i> ‐Sulfonic Acids
  作者：Zhiwei Ma、Zhe Zhou、László Kürti

  DOI：10.1002/anie.201705530

  日期：2017.8.7

  A RhII-catalyzed direct and stereospecific N-H- and N-alkyl aziridination of olefins is reported that uses hydroxylamine-O-sulfonic acids as inexpensive, readily available, and nitro group-free aminating reagents. Unactivated olefins, featuring a wide range of functional groups, are converted into the corresponding N-H or N-alkyl aziridines in good to excellent yields. This operationally simple, scalable

  据报道，Rh II催化的烯烃的直接和立体有择的N -H-和N-烷基叠氮化使用廉价的，容易获得的和无硝基的胺化试剂使用羟胺-O-磺酸。未活化的烯烃，具有宽范围的官能团的，被转化成相应的Ñ -H或ñ -烷基氮丙啶以良好至优异的产量。此操作简单，可扩展的转换在环境温度下有效进行，并且耐氧气和微量水分。
• Metal- and Additive-Free Intermolecular Aziridination of Olefins Using N-Boc-O-tosylhydroxylamine
  作者：Jawahar L. Jat、Bhoopendra Tiwari、Dinesh Chandra、Puneet Kumar、Vikram Singh

  DOI：10.1055/a-1879-7974

  日期：2022.10

  A metal and additive-free stereospecific direct N-H and N-Me aziridination of inactivated olefins is disclosed using N-Boc-O-tosyl­hydroxylamine (TsONHBoc) as an aminating agent in hexafluoroisopropanol (HFIP). The use of TsONHBoc, which generates the free aminating agent in situ under the reaction conditions, has several inherent advantages over other similar agents, such as low cost, easy access

  公开了在六氟异丙醇 (HFIP) 中使用N -Boc- O-甲苯磺酰基羟胺 ( TsONHBoc ) 作为胺化剂，对灭活烯烃进行无金属和无添加剂的直接N - H 和N -Me 氮丙啶化。使用在反应条件下原位生成游离胺化剂的 TsONHBoc与其他类似试剂相比具有几个固有的优势，例如成本低、易于获取以及在较长时间内储存期间的稳定性（非爆炸性）。