(2S,3S)-1-Benzyl-3-methyl-aziridine-2-carbaldehyde

• 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: (2S,3S)-1-Benzyl-3-methyl-aziridine-2-carbaldehyde
• 英文别名: (2S,3S)-1-benzyl-3-methylaziridine-2-carbaldehyde
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: RPMHQZHJMJNRMP-WKAHHKJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-1-Benzyl-3-methyl-aziridine-2-carbaldehyde 在 zirconocene hydrochloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 14.5h， 生成 N-苄基-N-(1-环丙基乙基)胺
  参考文献：
  名称：

  Hydrozirconation of alkenyloxirane derivatives: Preparation of cycloalkylmethanols

  摘要：

  Cyclopentyl and cyclopropylmethanol derivatives were efficiently prepared through a chemoselective hydrozirconation reaction of (1-butenyl)oxirane and vinyloxirane with Cp2ZrHCl. However, the attemped reaction of (1-pentenyl)oxirane or (1-propenyl)oxirane failed to yield cyclohexyl or cyclobutylmethanols. The ring formation was stereospecific and proceeded with the inversion of the configuration at the reacting oxirane carbon. The origin of stereospecificity and the stereoselectivity in the formation of cyclopropylmethanols was presumed by the approach of the Schwartz reagent from the less hindered site of the stable gauche-conformer of the vinyloxirane compound in the transition state. (Cyclopropylmethyl)amine derivatives were also prepared by the treatment of vinylaziridine derivatives with Cp2ZrHCl. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10340-4
• 作为产物：
  描述：

  N-苄基苏氨酸甲酯 在 四氯化碳 、 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 21.0h， 生成 (2S,3S)-1-Benzyl-3-methyl-aziridine-2-carbaldehyde
  参考文献：
  名称：

  A new route to functionalised π-allyltricarbonyliron lactam complexes from aziridines and their use in stereoselective synthesis and oxidative conversion to β-lactams

  摘要：

  氮丙啶烯酮能以良好的收率转化为侧链中含有酮官能团的Ï-烯丙基三羰基内酰胺铁络合物；在这些络合物的侧链中加入各种亲核剂，能以良好的收率和优异的脱氧率（>95%）生成仲醇和叔醇，这些醇在与三甲胺 N-氧化物处理后能以良好的收率生成相应的δ-内酰胺。

  DOI：

  10.1039/a806236f

文献信息

• Photoreactions of β-aziridinylacrylonitriles and acrylates with alkenes: the substituent effects on the formation of [3+2] cycloadducts
  作者：Keitaro Ishii、Takuya Sone、Takahide Shigeyama、Masahiro Noji、Shigeo Sugiyama

  DOI：10.1016/j.tet.2006.08.098

  日期：2006.11

  photoreactions of N-tritylaziridines 7–9 possessing diester, dinitrile, and butadiene groups in the side chain with electron-deficient alkenes yielded 2,3-cis-pyrrolidine derivatives 29, 30, and 33 exclusively. In particular, the dinitrile 8 also reacted with non-electron-deficient alkenes. The formal synthesis of the indolizidine fragment 10 of stellettamides starting from the pyrrolidine (E)-33 was achieved in

  光化学C，三取代的氮丙啶的C-键裂解3 - 6和随之而来的[3 + 2]与缺电子烯烃的环加成，得到新颖的头-头加成物（1,2,3,5-四取代的吡咯烷）和有选择地有效率的。氮丙啶3和5与分子氧反应，分别得到二恶唑烷26和裂解产物。结果可能表明，氮丙啶的C，C键双自由基裂解。的光反应Ñ -tritylaziridines 7 - 9具有二酯，二腈，和丁二烯基团与缺电子烯烃侧链，得到2,3-顺式吡咯烷衍生物29，30，和33只。特别地，二腈8也与非电子不足的烯烃反应。的吲哚里片段的正式合成10从吡咯烷（起始stellettamides的ë） - 33被以方便的方式来实现。
• Efficient synthesis of syn-aziridino alcohols by chelation-controlled addition of dialkylzincs and Grignard reagents to N-benzylaziridino aldehydes
  作者：JoséM. Andrés、Noemí de Elena、Rafael Pedrosa、Alfonso Pérez-Encabo

  DOI：10.1016/s0040-4020(99)00879-0

  日期：1999.12

  N-Benzyl aziridino aldehydes, derived from (L)-serine and (L)-threonine react with dialkylzinc and alkylmagnesium halides leading to syn-aziridino alcohols as single or major stereoisomers. The diastereoselec tivity is affected by the nature of the organometallic and the solvent system.

  衍生自（L）-丝氨酸和（L）-苏氨酸的N-苄基叠氮基醛与二烷基锌和卤化烷基镁反应，生成单一或主要的立体异构体的合成叠氮基醇。非对映选择性受有机金属和溶剂体系性质的影响。
• Hydrozirconation of alkenyloxirane derivatives: Preparation of cycloalkylmethanols
  作者：Susumu Harada、Noboru Kowase、Nobuhito Tabuchi、Takeo Taguchi、Yasuo Dobashi、Akira Dobashi、Yuji Hanzawa

  DOI：10.1016/s0040-4020(97)10340-4

  日期：1998.1

  Cyclopentyl and cyclopropylmethanol derivatives were efficiently prepared through a chemoselective hydrozirconation reaction of (1-butenyl)oxirane and vinyloxirane with Cp2ZrHCl. However, the attemped reaction of (1-pentenyl)oxirane or (1-propenyl)oxirane failed to yield cyclohexyl or cyclobutylmethanols. The ring formation was stereospecific and proceeded with the inversion of the configuration at the reacting oxirane carbon. The origin of stereospecificity and the stereoselectivity in the formation of cyclopropylmethanols was presumed by the approach of the Schwartz reagent from the less hindered site of the stable gauche-conformer of the vinyloxirane compound in the transition state. (Cyclopropylmethyl)amine derivatives were also prepared by the treatment of vinylaziridine derivatives with Cp2ZrHCl. (C) 1997 Elsevier Science Ltd. All rights reserved.
• A new route to functionalised π-allyltricarbonyliron lactam complexes from aziridines and their use in stereoselective synthesis and oxidative conversion to β-lactams
  作者：Steven V. Ley、Ben Middleton

  DOI：10.1039/a806236f

  日期：——

  Aziridinyl enones can be converted in good yield into π-allyltricarbonyliron lactam complexes bearing ketone functionality in the side chain; addition of a variety of nucleophiles into the side chains of these complexes proceeds in good yield and excellent (>95%) de to afford secondary and tertiary alcohols which on treatment with trimethylamine N-oxide form the corresponding β-lactams in good yield.

  氮丙啶烯酮能以良好的收率转化为侧链中含有酮官能团的Ï-烯丙基三羰基内酰胺铁络合物；在这些络合物的侧链中加入各种亲核剂，能以良好的收率和优异的脱氧率（>95%）生成仲醇和叔醇，这些醇在与三甲胺 N-氧化物处理后能以良好的收率生成相应的δ-内酰胺。