5-(碘甲基)-2-苯基-4,5-二氢-1,3-噻唑 | 906451-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(碘甲基)-2-苯基-4,5-二氢-1,3-噻唑
• 英文名称: 5-iodomethyl-2-phenyl-2-thiazoline
• 英文别名: Thiazole, 4,5-dihydro-5-(iodomethyl)-2-phenyl-；5-(iodomethyl)-2-phenyl-4,5-dihydro-1,3-thiazole
• CAS: 906451-57-8
• 化学式: C₁₀H₁₀INS
• 分子量: 303.167
• InChiKey: QAMCWYLLRVWNMT-UHFFFAOYSA-N

物化性质

• 沸点：
  377.0±34.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-allylbenzothioamide 在 次氯酸叔丁酯 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以77%的产率得到5-(碘甲基)-2-苯基-4,5-二氢-1,3-噻唑
  参考文献：
  名称：

  N杂环的实用便捷合成：在中性条件下用t-BuOI立体选择性地环化N-烯基酰胺。

  摘要：

  [结构：见正文]叔丁基次碘酸盐（t-BuOI）被发现是在极端温和条件下环化N-烯基酰胺的强大试剂，可导致多种N-杂环。当在反应中使用N-烯基磺酰胺时，以完全的立体选择性，以良好至优异的产率获得了三元至六元饱和N-杂环。该方法适用于烯基苯甲酰胺衍生物的环化以提供N-，O-或N-，S-杂环。

  DOI：

  10.1021/ol061182q

文献信息

• Practical and Convenient Synthesis of <i>N</i>-Heterocycles:  Stereoselective Cyclization of <i>N</i>-Alkenylamides with <i>t</i>-BuOI under Neutral Conditions
  作者：Satoshi Minakata、Yoshinobu Morino、Yoji Oderaotoshi、Mitsuo Komatsu

  DOI：10.1021/ol061182q

  日期：2006.7.1

  [Structure: see text] tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for the cyclization of N-alkenylamides leading to a variety of N-heterocycles under extremely mild conditions. When N-alkenylsulfonamides were employed in the reaction, three- to six-membered saturated N-heterocycles were obtained in good to excellent yields with complete stereoselectivity. The method was applicable

  [结构：见正文]叔丁基次碘酸盐（t-BuOI）被发现是在极端温和条件下环化N-烯基酰胺的强大试剂，可导致多种N-杂环。当在反应中使用N-烯基磺酰胺时，以完全的立体选择性，以良好至优异的产率获得了三元至六元饱和N-杂环。该方法适用于烯基苯甲酰胺衍生物的环化以提供N-，O-或N-，S-杂环。
• Electrophilic cyclization of N-alkenylamides using a chloramine-T/I2 system
  作者：Yoshinobu Morino、Ikumasa Hidaka、Yoji Oderaotoshi、Mitsuo Komatsu、Satoshi Minakata

  DOI：10.1016/j.tet.2006.10.003

  日期：2006.12

  A new protocol for the cyclization of N-alkenylamides using chloramine-T and iodine is described. When N-alkenylsulfonamides are treated with chloramine-T and iodine, three- to six-membered N-heterocycles are obtained with complete stereoselectivity. The method is compatible with the cyclization of the allylbenzamide or allylbenzthioamide to afford an oxazoline or thiazoline derivative, respectively. Mechanistic studies indicate that the chloramine-T/I-2 system functions as an effective iodonium species. (c) 2006 Elsevier Ltd. All rights reserved.
• Modular Preparation of 5-Halomethyl-2-oxazolines via PhI(OAc)₂-Promoted Intramolecular Halooxygenation of <i>N</i>-Allylcarboxamides
  作者：Gong-Qing Liu、Chun-Hua Yang、Yue-Ming Li

  DOI：10.1021/acs.joc.5b01832

  日期：2015.11.20

  A new method for the construction of oxazoline moiety was detailed. Using (diacetoxyiodo)benzene (PIDA) as the reaction promoter and halotrimethylsilane as the halogen source, intramolecular halooxygenation and halothionation of N-allylcarboxamides/N-allylcarbothioamides proceeded readily, leading : to the corresponding 5-halomethyloxazolines/5-halomethylthiazolines in good to excellent isolated yields. The 5-halomethyl products could be converted to different derivatives via conventional nucleophilic substitution methods. The reactions were carried out using easily available starting materials, and did not need harsh reaction conditions. All these features made this reaction a viable method for the construction of different oxazoline and thiazoline structures.