3-氯-3-异丙基-3H-双吖丙啶 | 29648-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环化合物
• 中文名称: 3-氯-3-异丙基-3H-双吖丙啶
• 英文名称: isopropylchlorodiazirine
• 英文别名: 3-Chloro-3-(propan-2-yl)-3H-diazirene；3-chloro-3-propan-2-yldiazirine
• CAS: 29648-80-4
• 化学式: C₄H₇ClN₂
• 分子量: 118.566
• InChiKey: HCUNOAVIUSXYTR-UHFFFAOYSA-N

物化性质

• 沸点：
  96.4±50.0℃ (760 Torr)
• 密度：
  1.31±0.1 g/cm3 (20 ºC 760 Torr)
• 闪点：
  12.1±30.1℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氯-3-异丙基-3H-双吖丙啶 以 正庚烷 为溶剂， 生成 Isopropylchlorocarbene
  参考文献：
  名称：

  The 1,2-hydrogen-shift rearrangement in alkylchlorocarbenes

  摘要：

  DOI：

  10.1021/ja00199a078
• 作为产物：
  描述：

  N,N'-dichloroisobutyrimidamide 在 sodium hydroxide 、 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 以49%的产率得到3-氯-3-异丙基-3H-双吖丙啶
  参考文献：
  名称：

  Mechanism of Graham's reaction

  摘要：

  DOI：

  10.1021/jo00337a061

文献信息

• Competitive rearrangements of alkylacetoxycarbenes
  作者：Robert A Moss、Song Xue、Wei Ma、Huarong Ma

  DOI：10.1016/s0040-4039(97)00936-2

  日期：1997.6

  Absolute rate constants are determined for (1,2) acetyl, carbon, and hydride shifts in cyclobutylacetoxycarbene and isopropylacetoxycarbene; comparative reactivities are examined.

  确定环丁基乙酰氧基卡宾和异丙基乙酰氧基卡宾中的（1,2）乙酰基，碳原子和氢化物位移的绝对速率常数；比较了反应性。
• A Nonspectroscopic Method To Determine the Photolytic Decomposition Pathways of 3-Chloro-3-alkyldiazirine:  Carbene, Diazo and Rearrangement in Excited State
  作者：Takatsugu Wakahara、Yasuyuki Niino、Takashi Kato、Yutaka Maeda、Takeshi Akasaka、Michael T. H. Liu、K. Kobayashi、S. Nagase

  DOI：10.1021/ja0116876

  日期：2002.8.1

  of carbene, diazo compound, and for the rearranged product via the excited state in the photolysis of 3-chloro-3-isopropyldiazirine and 3-chloro-3-chloromethyldiazirine. The carbene adds to C(60) to form methanofullerene, whereas the diazo compound adds to C(60) to form fulleroid. The olefin product arises as a result of the rearrangement in the excited state.

  C(60) 充当形成卡宾、重氮化合物以及通过 3-chloro-3-isopropyldiazirine 和 3-chloro-3-chloromethyldiazirine 光解中的激发态重排产物的机制探针。卡宾与 C(60) 相加形成甲烷富勒烯，而重氮化合物与 C(60) 相加形成富勒烯。烯烃产物是激发态重排的结果。
• Quantum Yield of Formation of Diazo Compounds from the Photolysis of Diazirines
  作者：Roland Bonneau、Michael T. H. Liu

  DOI：10.1021/ja9613217

  日期：1996.1.1
• Laser Flash Photolysis Study of Alkylhalocarbenes Generated from Non-Nitrogenous Precursors
  作者：Marc Robert、Igor Likhotvorik、Matthew S. Platz、Sarah C. Abbot、Mary M. Kirchhoff, and、Richard Johnson

  DOI：10.1021/jp972464y

  日期：1998.2.1

  Previously we have studied the photochemistry of alkylchlorodiazirines using laser flash photolysis methods and the pyridine ylide technique (White et al. J. Org. Chem. 1992, 17, 2841). The yield of trappable carbene was found to be a sensitive function of the alkylcarbene structure. This was attributed to ring opening of the diazirine to form a biradical which could suffer rearrangement, in addition to fragmentation to a carbene. It was also possible to explain the data in terms of a carbene-pyridine complex which can either rearrange or collapse to an ylide. In this work, alkylchlorocarbenes are generated from phenanthridenes. The results do not rule out the intermediacy of a carbene-pyridine complex; however, if this species is formed, it does not rearrange to chloroalkene in competition with collapse to form an ylide. This study reduces the urgency with which to postulate carbene-olefin complexes (Tomioka et al. J. Am. Chem. Soc. 1984, 106, 454).
• Mechanism of Graham's reaction
  作者：Robert A. Moss、Joanna Wlostowska、Wenjeng Guo、Michal Fedorynski、James P. Springer、Jordan M. Hirshfield

  DOI：10.1021/jo00337a061

  日期：1981.11