1-phenyl-3--2(3H)-indolizinone | 74360-65-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-phenyl-3--2(3H)-indolizinone
• 英文别名: (3Z)-3-[methylsulfanyl(sulfanyl)methylidene]-1-phenylindolizin-2-one
• CAS: 74360-65-9
• 化学式: C₁₆H₁₃NOS₂
• 分子量: 299.417
• InChiKey: IXLXJURNKQHORP-PEZBUJJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.31
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-phenyl-3--2(3H)-indolizinone 在 potassium carbonate 、 三乙胺 作用下， 以 氯仿 、 苯 为溶剂， 反应 48.0h， 生成 4-Ethoxy-2-oxo-10-phenyl-2H-pyrano[2,3-b]indolizine-3-carbonitrile
  参考文献：
  名称：

  新的氮桥杂环的制备。吡喃并[2,3-b]吲哚嗪酮衍生物的简便合成方法

  摘要：

  在碱存在下，通过 3-[双（烷硫基）亚甲基]-2,3-二氢吲哚嗪-2-酮与各种乙酸酯的反应，以 18-98% 的产率形成吡喃并 [2,3-b] 吲哚嗪酮衍生物。通过 1-[2,2-双（烷硫基）-1-乙氧基羰基乙烯基]-2-乙基吡啶鎓碘化物和-2-甲基吡啶鎓碘化物的碱处理或通过 3-[（烷硫基）巯基亚甲基的 S-烷基化，很容易获得二氢茚茚酮]-1-苯基-2,3-dihydroindolizin-2-ones 与烷基碘。

  DOI：

  10.1246/bcsj.53.1115
• 作为产物：
  描述：

  二硫化碳 、 2-benzyl-1-(ethoxycarbonylmethyl)pyridinium bromide 、 硫酸二甲酯 在 base 作用下， 生成 1-phenyl-3--2(3H)-indolizinone
  参考文献：
  名称：

  Preparation of New Nitrogen-Bridged Heterocycles. 46. Selective Formation of 4(1H)-8,8a-Dihydro-1,4-thiazino[3,4,5-cd]indolizinone and (E)-3-(1,3-Oxathiol-2-ylidene)-2(3H)-indolizinone Derivatives.

  摘要：

  (Z)-3-[巯基(甲硫基)亚甲基]-2(3H)-吲嗪酮与溴乙腈和溴乙酸酯在碱存在下的反应得到了相应的 4(1H)-8，8a-二氢-1，4-噻嗪并[3，4，5-cd]吲嗪酮衍生物、但用一些苯酰基溴化物对相同化合物进行类似处理，可得到一种完全不同类型的产物--(E)-3-(5-芳基-1, 3-氧硫杂环戊烯-2-亚基)-2(3H)-吲嗪酮，产率为 12-74%，并伴有甲硫醇的演化。有趣的是，(Z)-3-[巯基（苯硫基）亚甲基]-2(3H)-吲嗪酮与碘甲烷在碱存在下的反应并没有得到预期的(Z)-3-(5-芳基-1, 3-氧硫杂环戊-2-亚基)-2(3H)-吲嗪酮，而只得到了相同的(E)-异构体，产率为 22-53%。通过 X 射线分析，确定这些 3-(5-芳基-1, 3-氧硫杂环戊-2-亚基)-2(3H)-吲嗪酮中 C3-C2' 双键的立体化学结构为 (E)。

  DOI：

  10.1248/cpb.46.1866

文献信息

• Preparation of New Nitrogen-Bridged Heterocycles. 28. First Syntheses of 1,3-Oxazino[6,5-<i>b</i>]indolizine Derivatives
  作者：Akikazu Kakehi、Suketaka Ito、Tosio Sakurai、Kunio Urushido、Susumu Hatanaka、Kouji Sugiura

  DOI：10.1246/bcsj.64.3296

  日期：1991.11

  The reactions of 2-[mercapto(methylthio)methylene]-2(3H)-indolizinones with alkyl isothiocyanates in the presence of potassium t-butoxide in N,N-dimethylformamide afforded new heterocycles, 3-alkyl-2H-1,3-oxazino[6,5-b]indolizine-2,4(3H)-dithione derivatives, in moderate yields. On the other hand, their reactions with phenyl isothiocyanate did not afford the corresponding 2H-1,3-oxazino[6,5-b]indolizine-2,4(3H)-dithiones, although the reaction of 2-[mercapto(methylthio)methylene]-1-methyl-2(3H)-indolizinone with phenyl isothiocyanate gave 10-methyl-3-phenyl-2-phenylimino-2,3-dihydro-4H-1,3-oxazino[6,5-b]indolizine-4-thione in a very low yield (10%). The structures of these 2H-1,3-oxazino[6,5-b]indolizine-2,4(3H)-dithiones and the 2-phenylimino analogue were determined by inspections of their physical and spectral data and by a single crystal X-ray analysis of one of these compounds.

  在N,N-二甲基甲酰胺中，2-[巯基(甲硫基)亚甲基]-2(3H)-吲哚嗪酮与烷基异硫氰酸酯在叔丁醇钾存在下反应，以中等的产率得到了新的杂环化合物，即3-烷基-2H-1,3-恶嗪并[6,5-b]吲哚嗪-2,4(3H)-二硫酮衍生物。另一方面，它们与苯基异硫氰酸酯的反应并未得到相应的2H-1,3-恶嗪并[6,5-b]吲哚嗪-2,4(3H)-二硫酮，尽管2-[巯基(甲硫基)亚甲基]-1-甲基-2(3H)-吲哚嗪酮与苯基异硫氰酸酯反应生成了10-甲基-3-苯基-2-苯亚胺-2,3-二氢-4H-1,3-恶嗪并[6,5-b]吲哚嗪-4-硫酮，但产率极低（10%）。这些2H-1,3-恶嗪并[6,5-b]吲哚嗪-2,4(3H)-二硫酮及其2-苯亚胺类似物的结构通过其物理和光谱数据检测以及其中一种化合物的单晶X射线分析确定。
• A New Synthetic Approach to Some Functionalized Cycl[3.2.2]azine Derivatives
  作者：Akikazu Kakehi、Hideyuki Muranaka、Hiroyuki Suga、Kennosuke Itoh

  DOI：10.3987/com-10-s(e)72

  日期：——

  Dehydrogenation of some ethyl 4-oxo-1H-8,8a-dihydro-1,4-thiazino[3,4,5-cd]indolizine-1-carboxylates with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) were examined. No simply dehydrogenated products such as 4-oxo-1H- and 4-oxo-8H-1,4-thiazino[3,4,5-cd]indolizines or their full conjugated enol forms could be obtained, but ethyl cycl[3.2.2]azine-1-carboxylates were directly obtained via the cyclization and the subsequent desulfurization of the 4H-1,4-thiazine ring in the dehydrogenated intermediates.
• Preparation of New Nitrogen-bridged Heterocycles. A Facile Synthetic Method of Pyrano[2,3-<i>b</i>]indolizinone Derivatives
  作者：Akikazu Kakehi、Suketaka Ito、Kazunori Nakanishi、Kozo Watanabe、Masahiko Kitagawa

  DOI：10.1246/bcsj.53.1115

  日期：1980.4

  Pyrano[2,3-b]indolizinone derivatives were formed in 18–98% yields by the reactions of 3-[bis(alkylthio)methylene]-2,3-dihydroindolizin-2-ones with various acetates in the presence of alkali. Dihydroindolizinones were readily obtained by the alkaline treatment of 1-[2,2-bis(alkylthio)-1-ethoxycarbonylvinyl]-2-ethylpyridinium iodides and -2-methylpyridinium iodides or by the S-alkylation of 3-[(alk

  在碱存在下，通过 3-[双（烷硫基）亚甲基]-2,3-二氢吲哚嗪-2-酮与各种乙酸酯的反应，以 18-98% 的产率形成吡喃并 [2,3-b] 吲哚嗪酮衍生物。通过 1-[2,2-双（烷硫基）-1-乙氧基羰基乙烯基]-2-乙基吡啶鎓碘化物和-2-甲基吡啶鎓碘化物的碱处理或通过 3-[（烷硫基）巯基亚甲基的 S-烷基化，很容易获得二氢茚茚酮]-1-苯基-2,3-dihydroindolizin-2-ones 与烷基碘。
• Preparation of New Nitrogen-Bridged Heterocycles. 46. Selective Formation of 4(1H)-8,8a-Dihydro-1,4-thiazino[3,4,5-cd]indolizinone and (E)-3-(1,3-Oxathiol-2-ylidene)-2(3H)-indolizinone Derivatives.
  作者：Akikazu KAKEHI、Suketaka ITO、Hiroyuki SUGA、Toshiyuki KOBAYASHI、Susumu HATANAKA

  DOI：10.1248/cpb.46.1866

  日期：——

  The reactions of (Z)-3-[mercapto(methylthio)methylene]-2(3H)-indolizinones with bromoacetonitrile and bromoacetates in the presence of a base gave the corresponding 4(1H)-8, 8a-dihydro-1, 4-thiazino[3, 4, 5-cd]indolizinone derivatives, but similar treatment of the same compounds with some phenacyl bromides provided a quite different type of product, (E)-3-(5-aryl-1, 3-oxathiol-2-ylidene)-2(3H)-indolizinones, in 12-74% yield with the evolution of methanethiol. Interestingly, the reactions of (Z)-3-[mercapto(phenacylthio)methylene]-2(3H)-indolizinones and iodomethane in the presence of a base did not afford the expected (Z)-3-(5-aryl-1, 3-oxathiol-2-ylidene)-2(3H)-indolizinones, but gave only the same (E)-isomers in 22-53% yields. The stereochemistry about the C3-C2' double bond in these 3-(5-aryl-1, 3-oxathiol-2-ylidene)-2(3H)-indolizinones was determined to be (E) by X-ray analysis.

  (Z)-3-[巯基(甲硫基)亚甲基]-2(3H)-吲嗪酮与溴乙腈和溴乙酸酯在碱存在下的反应得到了相应的 4(1H)-8，8a-二氢-1，4-噻嗪并[3，4，5-cd]吲嗪酮衍生物、但用一些苯酰基溴化物对相同化合物进行类似处理，可得到一种完全不同类型的产物--(E)-3-(5-芳基-1, 3-氧硫杂环戊烯-2-亚基)-2(3H)-吲嗪酮，产率为 12-74%，并伴有甲硫醇的演化。有趣的是，(Z)-3-[巯基（苯硫基）亚甲基]-2(3H)-吲嗪酮与碘甲烷在碱存在下的反应并没有得到预期的(Z)-3-(5-芳基-1, 3-氧硫杂环戊-2-亚基)-2(3H)-吲嗪酮，而只得到了相同的(E)-异构体，产率为 22-53%。通过 X 射线分析，确定这些 3-(5-芳基-1, 3-氧硫杂环戊-2-亚基)-2(3H)-吲嗪酮中 C3-C2' 双键的立体化学结构为 (E)。