2-(p-chlorobenzyl)-1-(ethoxycarbonylmethyl)pyridinium bromide | 133303-48-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(p-chlorobenzyl)-1-(ethoxycarbonylmethyl)pyridinium bromide
• 英文别名: 1-ethoxycarbonylmethyl-2-(p-chlorobenzyl)pyridinium bromide；ethyl 2-[2-[(4-chlorophenyl)methyl]pyridin-1-ium-1-yl]acetate;bromide
• CAS: 133303-48-7
• 化学式: Br*C₁₆H₁₇ClNO₂
• 分子量: 370.673
• InChiKey: PNXUHNDEZADDMQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.21
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.18
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(p-chlorobenzyl)-1-(ethoxycarbonylmethyl)pyridinium bromide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 2.17h， 生成 ethyl 3-benzylthio-5-(p-chlorophenyl)-4-oxo-1H-8,8a-dihydro-1,4-thiazino[3,4,5-cd]indolizine-1-carboxylate
  参考文献：
  名称：

  A New Synthetic Approach to Some Functionalized Cycl[3.2.2]azine Derivatives

  摘要：

  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.

  DOI：

  10.3987/com-10-s(e)72

文献信息

• Preparation of New Nitrogen-Bridged Heterocycles. 25. A Smooth Synthesis of [1,4]Thiazino[3,4,5-<i>cd</i>]indolizine Derivatives
  作者：Akikazu Kakehi、Suketaka Ito、Tsuneo Fujii、Tosio Sakurai、Kunio Urushido、Susumu Hatanaka、Toshiaki Mabuchi、Shun-ichiro Matsushita

  DOI：10.1246/bcsj.63.3571

  日期：1990.12

  The title compounds were prepared smoothly in moderate yields by the reactions of 3-(mercaptomethylene)-2(3H)-indolizinones with various alkylating agents such as bromoacetonitrile, bromoacetates, and phenacyl bromides in the presence of base. The structural assignments of these products were accomplished by their spectral inspections, and the structure for one compound was distinctly proven by its

  在碱的存在下，通过 3-(巯基亚甲基)-2(3H)-吲哚满酮与各种烷基化剂如溴乙腈、溴乙酸盐和苯甲酰溴反应，以中等产率顺利制备了标题化合物。这些产品的结构分配是通过光谱检查完成的，一种化合物的结构由其 X 射线晶体学明确证明。为了解释该反应中的区域选择性，还使用模型化合物进行了分子轨道计算 (CNDO/2)。
• 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)。
• KAKEHI, AKIKAZU;ITO, SUKETAKA;FUJII, TSUNEO;SAKURAI, TOSIO;URUSHIDO, KUNI+, BULL. CHEM. SOC. JAP., 63,(1990) N2, C. 3571-3578
  作者：KAKEHI, AKIKAZU、ITO, SUKETAKA、FUJII, TSUNEO、SAKURAI, TOSIO、URUSHIDO, KUNI+

  DOI：——

  日期：——