2-phenyl-3-oximino-3H-indole | 4676-99-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-phenyl-3-oximino-3H-indole
• 英文别名: 2-phenyl-indol-3-one oxime；2-phenyl-indole-3-one oxime；2-Phenyl-indol-3-on-oxim；3-Oximino-2-phenyl-indolenin；2-Phenyl-3H-indolon-(3)-oxim；3-Oximo-2-phenyl-indolenin
• CAS: 4676-99-7
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: UNTADALETIMKJL-UHFFFAOYSA-N

物化性质

• 熔点：
  280 °C (decomp)
• 沸点：
  432.2±28.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.95
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-phenyl-3-oximino-3H-indole 在 乙醚 、 五氯化磷 作用下， 生成 2-苯基-4-[3H]喹唑啉酮
  参考文献：
  名称：

  Alessandri, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1913, vol. <5> 22 II, p. 153,230

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯基吲哚-3-酮 在 乙醇 、 盐酸羟胺 、 sodium acetate 作用下， 生成 2-phenyl-3-oximino-3H-indole
  参考文献：
  名称：

  Social Psychological Models of Choice Behavior and Drivers' Left Turns

  摘要：

  The authors reanalyzed data from a simulated left-turn experiment (P A. Hancock, J. K. Caird, S. Shekhar, & M. Vercruyssen, 1991) to test the adequacy of the nonlinear Gray-Tallman satisfaction balance model of choice behavior (L. N. Gray & I. Tallman, 1984) in predicting left turns. Participants (Hancock et al., 1991) were 40 experienced U.S. drivers who were exposed to simulated oncoming traffic; the size of the vehicle (motorcycle, compact vehicle, full-sized vehicle, delivery truck), its speed (10-70 mph, or 16-112 kmph), and the intervehicle time gap (3-9 s) varied. Hancock et al. (1991) measured (a) the likelihood of a left turn and (b) the occurrence of a collision. The probability of a left turn was greater for larger intervehicle time gaps and for oncoming smaller vehicles traveling at higher speeds. The Gray-Tallman (1984) model explained 69% of the variation in turning versus 57% for a linear regression model. In making decisions people tend to treat the values and costs affecting choices in a multiplicative, rather than linear, fashion. The Gray-Tallman model also has the potential for incorporating, both theoretically and mathematically, an unlimited range of potential values and costs that may influence left turn decisions.

  DOI：

  10.1080/00224540109600583

文献信息

• NaNO ₂ /K ₂ S ₂ O ₈ ‐mediated Selective Radical Nitration/Nitrosation of Indoles: Efficient Approach to 3‐Nitro‐ and 3‐Nitrosoindoles
  作者：Adedamola Shoberu、Cheng‐Kun Li、Ze‐Kun Tao、Guo‐Yu Zhang、Jian‐Ping Zou

  DOI：10.1002/adsc.201900070

  日期：2019.5.14

  JPZ acknowledges financial support from the National Natural Science Foundation of China (No. 21172163, 21472133), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), and Key Laboratory of Organic Synthesis of Jiangsu Province (KJS1749).

  JPZ感谢国家自然科学基金（No. 21172163，21472133），江苏省高等学校优先学术计划（PAPD）和江苏省有机合成重点实验室（KJS1749）的资助。
• <i>tert</i>-Butyl Nitrite Mediated Synthesis of Fluorinated <i>O</i>-Alkyloxime Ether Derivatives
  作者：Xingxing Ma、Qiuling Song

  DOI：10.1021/acs.orglett.9b02689

  日期：2019.9.20

  A tert-butyl nitrite (TBN)-mediated synthesis of fluorinated O-alkyloxime ether derivatives with bromodifluoroalkyl reagents as the fluorine sources has been developed. A variety of halodifluorinated compounds were found compatible, delivering the desired products in moderate to excellent yields. This transformation features a simple operation, can be done in air, and found to involve radicals. This

  已经开发了以溴代二氟烷基试剂为氟源的亚硝酸叔丁酯（TBN）介导的氟化O-烷基肟醚衍生物的合成。发现多种卤代二氟化合物是相容的，以中等至优异的产率提供所需的产物。这种转换的特点是操作简单，可以在空气中完成，并且涉及自由基。该协议代表了一种直接的途径来访问各种氟化的O-烷基肟醚衍生物。
• Reactions of indoles with nitrogen dioxide and nitrous acid in an aprotic solvent
  作者：Paola Astolfi、Maria Panagiotaki、Corrado Rizzoli、Lucedio Greci

  DOI：10.1039/b607680g

  日期：——

  The reaction of 2-phenyl- and 1-methyl-2-phenylindole with nitrogen dioxide or with nitrous acid (NaNO2-CH3COOH) in benzene leads mainly to the formation of the isonitroso and 3-nitroso indole derivatives, respectively. When reacted with nitrous acid, 1-methyl-2-phenylindole gives also the corresponding azo-bis-indole in good yields. The reaction of indole with nitrogen dioxide leads to 2-(indol-3-yl)-3H-indol-3-one

  2-苯基-和1-甲基-2-苯基吲哚与二氧化氮或与亚硝酸（NaNO2-CH3COOH）在苯中的反应分别分别导致异亚硝基和3-亚硝基吲哚衍生物的形成。当与亚硝酸反应时，1-甲基-2-苯基吲哚也以良好的收率得到相应的偶氮-双吲哚。吲哚与二氧化氮的反应导致以2-（吲哚-3-基）-3H-吲哚-3-酮为主要产物以及少量的2-（吲哚-3-基）-3H-吲哚-3 -肟; 当相同的吲哚与亚硝酸反应时获得的主要产物为2-（吲哚-3-基）-3H-吲哚-3-肟。3-烷基取代的吲哚与二氧化氮的反应相当复杂，并导致形成不同的硝基吲哚，而当使用亚硝酸时观察到亚硝化。
• Three-component reaction of tert-butyl nitrite with indoles and halides: A facile and efficient synthesis of oxime ether derivatives
  作者：Zhongshan Wu、Ranran Zhu、Yang Yang、Yichu Wu、Zhonghua Wang、Fanhong Wu

  DOI：10.1016/j.tet.2023.133519

  日期：2023.8

  A mild and efficient one-pot method has been developed for the synthesis of oxime ether derivatives with up to 85% yield by employing tert-butyl nitrite (TBN) as nitrogen source, which occurs under room temperature and exhibits wide substrate scope. The single electron transfer mechanism and the cascade reactions approach have been confirmed.

  开发了一种以亚硝酸叔丁酯（TBN）为氮源，在室温下合成肟醚衍生物的温和高效的一锅法，收率高达85%，该反应在室温下发生，具有广泛的底物范围。单电子转移机制和级联反应方法已得到证实。
• Water vs. Organic Solvents: Water‐Controlled Divergent Reactivity of 2‐Substituted Indoles
  作者：Airu Hashidoko、Taku Kitanosono、Yasuhiro Yamashita、Shū Kobayashi

  DOI：10.1002/asia.202301045

  日期：2024.3

  Notwithstanding lack of ability to dissolve reactants, water exhibited superior performance to other media. 2-Methoxyethyl nitrite, which has been tailored for reactions in water, empowered this protocol. Chemoselective transformations of the products opens up access to a new chemical library. These results support the power of running organic reactions in water.

  已经开发出2-取代吲哚和丙二酸酯的选择性肟形成。尽管缺乏溶解反应物的能力，水仍表现出优于其他介质的性能。亚硝酸 2-甲氧基乙酯专为水中反应而设计，为该方案提供了支持。产品的化学选择性转化开辟了新化学库的途径。这些结果支持了在水中进行有机反应的能力。