1,3,5-tris(3-chloro-4-methylphenyl)-1,3,5-triazinane | 1448262-42-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,3,5-tris(3-chloro-4-methylphenyl)-1,3,5-triazinane
• CAS: 1448262-42-7
• 化学式: C₂₄H₂₄Cl₃N₃
• 分子量: 460.834
• InChiKey: GTVVIIRYXVRHNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,5-tris(3-chloro-4-methylphenyl)-1,3,5-triazinane 、 methyl 3-hydroxy-3-phenylprop-2-enedithioate 以 1,2-二氯乙烷 为溶剂， 以93%的产率得到(3-(3-chloro-4-methylphenyl)-6-(methylthio)-3,4-dihydro-2H-1,3-thiazin-5-yl)(phenyl)methanone
  参考文献：
  名称：

  Synthesis of 3,4-Dihydro-2H-1,3-thiazines from α-Enolic Dithioesters and 1,3,5-Triazinanes via a Formal (3 + 3) Annulation Reaction

  摘要：

  The synthesis of 3,4-dihydro-2H-1,3-thiazines from alpha-enolic dithioesters and 1,3,5-triazinanes has been achieved via a formal (3 + 3) annulation reaction under thermal conditions, where 1,3,5-triazinanes were utilized as three-atom synthons. This transformation is catalyst-free and additive-free.

  DOI：

  10.1021/acs.joc.0c01984
• 作为产物：
  描述：

  聚合甲醛 、 3-氯-4-甲基苯胺 以 甲苯 为溶剂， 生成 1,3,5-tris(3-chloro-4-methylphenyl)-1,3,5-triazinane
  参考文献：
  名称：

  钯催化配体引导乙烯基恶唑烷-2,4-二酮与 1,3,5-三嗪的发散脱羧环加成反应

  摘要：

  本研究展示了乙烯基恶唑烷-2,4-二酮与 1,3,5-三嗪烷的高效区域发散配体控制的钯催化环加成反应。在二膦配体存在下，反应通过(5+2)环加成途径进行，以优异的收率得到1,3-二氮杂卓-4-酮，而使用单膦配体时，反应通过(3+ 2)环加成途径以良好的产率得到咪唑烷-4-酮。

  DOI：

  10.1021/acs.orglett.3c04339

文献信息

• Access to Imidazolidines via 1,3-Dipolar Cycloadditions of 1,3,5-Triazinanes with Aziridines
  作者：Liang Tu、Zhenghui Li、Tao Feng、Shuyan Yu、Rong Huang、Jing Li、Wenxuan Wang、Yongsheng Zheng、Jikai Liu

  DOI：10.1021/acs.joc.9b01959

  日期：2019.9.6

  The unprecedented 1,3-dipolar cycloaddition of 1,3,5-triazinanes and aziridines has been described. With readily available starting material, this method offers efficient access to a wide range of functionalized imidazolidine derivatives in moderate to good yields (up to 92%) under mild conditions. Preliminary mechanistic investigations show that the ring opened zwitterionic pathway product dominated

  已经描述了前所未有的1,3,5-三嗪并与氮丙啶的1,3-偶极环加成反应。使用容易获得的起始原料，该方法可在温和条件下以中等至良好的收率（高达92％）有效获得各种功能化的咪唑烷衍生物。初步的机理研究表明，开环的两性离子途径产物比二阶亲核取代样产物占优势。该方案是非常有前途的，因为该反应是可扩展的，并且可以将产物通用转化为其他官能化的咪唑烷。
• Synthesis of 1,2,3,4‐Tetrahydrobenzofuro[3,2‐ <i>d</i> ]pyrimidines via [4+2] Annulation Reaction of 1,3,5‐Triazinanes and Aurone‐Derived α,β‐Unsaturated Imines
  作者：Bin Cheng、Xinping Zhang、Shengxian Zhai、Yixuan He、Qingqing Tao、Hui Li、Jian Wei、Haiyan Sun、Taimin Wang、Hongbin Zhai

  DOI：10.1002/adsc.202000713

  日期：2020.9.21

  A [4+2] annulation reaction of 1,3,5‐triazinanes and aurone‐derived α,β‐unsaturated imines has been developed, which enables the synthesis of 1,2,3,4‐tetrahydrobenzofuro[3,2‐d]pyrimidines under thermal conditions in high yields. This protocol is catalyst‐free and additive‐free.

  已开发出1,3,5-三嗪并与紫罗兰素衍生的α，β-不饱和亚胺进行[4 + 2]环合反应，从而可以合成1,2,3,4-四氢苯并呋喃[3,2- d在热条件下高产率制备嘧啶嘧啶。该协议不含催化剂和添加剂。
• Enantioselective formal [2 + 2 + 2] cycloaddition of 1,3,5-triazinanes to construct tetrahydropyrimidin-4-one derivatives
  作者：Peiran Ruan、Qiong Tang、Zun Yang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/d1cc06549a

  日期：——

  A chiral Lewis acid-catalyzed enantioselective formal [2 + 2 + 2] cycloaddition of 1,3,5-triazinanes with azlactones or β,γ-unsaturated pyrazole amides was developed to synthesize chiral tertiary/quaternary tetrahydropyrimidin-4-one derivatives with good yields and enantioselectivities. Two competitive reaction pathways were proposed based on experiments.

  1,3,5-三嗪烷与吖内酯或β,γ-不饱和吡唑酰胺的手性路易斯酸催化的对映选择性形式[2 + 2 + 2]环加成反应合成了具有良好性能的手性叔/季四氢嘧啶-4-酮衍生物。产率和对映选择性。基于实验提出了两种竞争反应途径。
• Synthesis of Hydrobenzoimidazoles from <i>para</i> ‐Quinamines and 1,3,5‐Triazinanes via a Formal [3+2] Annulation Reaction
  作者：Xinping Zhang、Bin Cheng、Hui Li、Yixuan He、Wei Xu、Xiaoguang Duan、Haiyan Sun、Taimin Wang、Hongbin Zhai

  DOI：10.1002/adsc.202001103

  日期：2021.1.19

  The synthesis of hydrobenzoimidazoles from para‐quinamines and 1,3,5‐triazinanes was achieved via a formal [3+2] annulation reaction in the presence of In(OTf)3 as the catalyst. Further studies demonstrated that the synthesis of hydrobenzooxazoles could also be accomplished via the same strategy from para‐quinols and 1,3,5‐triazinanes.

  在In（OTf）3作为催化剂的情况下，通过正式的[3 + 2]环化反应，由对喹胺和1,3,5-三嗪酮合成氢化苯并咪唑。进一步的研究表明，也可以通过对苯二酚和1,3,5-三嗪并酮的相同策略完成氢化苯并恶唑的合成。
• [3 + 2]-Cycloaddition of Azaoxyallyl Cations with Hexahydro-1,3,5-triazines: Access to 4-Imidazolidinones
  作者：Danqing Ji、Jiangtao Sun

  DOI：10.1021/acs.orglett.8b00951

  日期：2018.5.4

  A novel base-promoted [3 + 2] cycloaddition reaction of azaoxyallyl cations with hexahydro-1,3,5-triazines has been developed, affording 4-imidazolidinones in moderate to good yields under mild reaction conditions. This simple but efficient protocol features cycloaddition of two in situ formed reactive species in the absence of a transition-metal catalyst.

  已经开发了一种新的碱促进的氮杂烯丙基阳离子与六氢-1,3,5-三嗪的碱促进的[3 + 2]环加成反应，在温和的反应条件下以中等至良好的产率提供了4-咪唑啉酮。这种简单而有效的方案的特征是在不存在过渡金属催化剂的情况下环化两个原位形成的反应物种。