methyl 2-diazo-2-(3,4-dimethylphenyl)acetate | 1431564-27-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-diazo-2-(3,4-dimethylphenyl)acetate
• CAS: 1431564-27-0
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: QIJYWQVIIXUDGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  62.7
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl 2-diazo-2-(3,4-dimethylphenyl)acetate 在 盐酸 、 dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] 作用下， 以 乙醇 为溶剂， 生成 (2S,3S)-methyl 2-(3,4-dimethylphenyl)-3-hydroxy-3-phenylpropanoate
  参考文献：
  名称：

  用于高度官能化 2,3-二氢苯并呋喃的对映选择性合成的连续 C-H 官能化反应

  摘要：

  2,3-二氢苯并呋喃的对映选择性合成是通过使用两个连续的 CH 官能化反应来实现的，即铑催化的对映选择性分子间 CH 插入，然后是钯催化的 CH 活化/CO 环化。通过随后的钯催化分子间 Heck 型 sp(2) CH 功能化，2,3-二氢苯并呋喃结构的进一步多样化是可能的。

  DOI：

  10.1021/ja401731d

文献信息

• Asymmetric Counter-Anion-Directed Aminomethylation: Synthesis of Chiral β-Amino Acids via Trapping of an Enol Intermediate
  作者：Zhenghui Kang、Yongheng Wang、Dan Zhang、Ruibo Wu、Xinfang Xu、Wenhao Hu

  DOI：10.1021/jacs.8b12832

  日期：2019.1.30

  A novel enantioselective aminomethylation reaction of diazo compound, alcohol and α-aminomethyl ether enabled by asymmetric counteranion-directed catalysis is disclosed that offers an efficient and convenient access to furnish optically active α-hydroxyl-β-amino acids in high yield with high to excellent enantioselectivities. Control experiments and DFT calculations indicate that the transformation

  公开了一种通过不对称抗衡阴离子导向催化实现的重氮化合物、醇和 α-氨基甲基醚的新型对映选择性氨基甲基化反应，它提供了一种高效便捷的途径以高产率提供光学活性 α-羟基-β-氨基酸。对映选择性。对照实验和 DFT 计算表明，转化是通过用亚甲基亚胺离子捕获原位生成的烯醇中间体而进行的，不对称诱导是由手性五羧基环戊二烯阴离子通过氢键和静电相互作用实现的。
• Enantioselective Trapping of Oxonium Ylides by 3-Hydroxyisoindolinones via a Formal S_N1 Pathway for Construction of Contiguous Quaternary Stereocenters
  作者：Zhenghui Kang、Dan Zhang、Jiayi Shou、Wenhao Hu

  DOI：10.1021/acs.orglett.7b03916

  日期：2018.2.16

  acid co-catalyzed three-component reaction via trapping of oxonium ylides with 3-hydroxyisoindolinones by a formal SN1 pathway is described. This reaction allows for the efficient synthesis of isoindolinone derivatives with two contiguous quaternary stereogenic centers in high yields (up to 93%) with excellent enantioselectivities and moderate diastereoselectivities under mild reaction conditions.

  对映体选择性的Rh（II）/手性磷酸共催化通过由正式S下层捕获与3- hydroxyisoindolinones氧鎓叶立德三组分反应Ñ 1途径进行说明。该反应可以在温和的反应条件下，以高收率（高达93％）高效合成具有两个连续的季立体异构中心的异吲哚啉酮衍生物，并具有出色的对映选择性和中等非对映选择性。
• Co(II)-Catalyzed Regioselective Pyridine C–H Coupling with Diazoacetates
  作者：Haisheng Xie、Youxiang Shao、Jiao Gui、Jianyong Lan、Zhipeng Liu、Zhuofeng Ke、Yuanfu Deng、Huanfeng Jiang、Wei Zeng

  DOI：10.1021/acs.orglett.9b01196

  日期：2019.5.3

  A Co(II)-catalyzed pyridyl C–H bond carbenoid insertion with α-diazoacetates has been realized. This transformation features a highly regioselective C–C bond formation at the C3-position of pyridines, providing an efficient access to diverse α-aryl-α-pyridylacetates.

  已经实现了由Co（II）催化的带有α-重氮乙酸盐的吡啶基C–H键类胡萝卜素插入。这种转变的特征是在吡啶的C3位上具有高度区域选择性的C–C键形成，从而可以有效地获得各种α-芳基-α-吡啶基乙酸酯。
• Diastereoselective synthesis of isochromans <i>via</i> the Cu(<scp>ii</scp>)-catalysed intramolecular Michael-type trapping of oxonium ylides
  作者：Gopi Krishna Reddy Alavala、Farrukh Sajjad、Taoda Shi、Zhenghui Kang、Mingliang Ma、Dong Xing、Wenhao Hu

  DOI：10.1039/c8cc06390g

  日期：——

  skeleton was achieved by the copper(II)-catalyzed transformation of alcohol-tethered enones and diazo compounds. This transformation was proposed to proceed through the intramolecular Michael-type trapping of an in situ generated oxonium ylide intermediate. The copper(II) catalyst may play a dual role in catalyzing diazo decomposition as well as activating the enone unit. With this method, a series of 3

  通过铜（II）催化的醇系烯酮和重氮化合物的转化，实现了用于快速构建异色满骨架的高度非对映选择性的方法。提出该转化通过原位产生的氧鎓叶立德中间体的分子内迈克尔型捕集进行。铜（II）催化剂在催化重氮分解以及活化烯酮单元中可以起双重作用。用这种方法，可以在非常温和的反应条件下获得一系列具有极好的非对映选择性的3，4-取代的异色满。
• Rh(I)-Catalyzed Cross-Coupling of α-Diazoesters with Arylsiloxanes
  作者：Ying Xia、Zhen Liu、Sheng Feng、Fei Ye、Yan Zhang、Jianbo Wang

  DOI：10.1021/acs.orglett.5b00052

  日期：2015.2.20

  An Rh(I)-catalyzed cross-coupling of diazoesters with arylsiloxanes has been successfully achieved. This transformation is a new method for the construction of the C(sp(3))C(sp(2)) bond, thus providing an alternative synthesis of a-aryl esters. Rh(I)carbene migratory insertion has been proposed to be involved in this coupling reaction. The reaction represents the first example of utilizing arylsiloxane as the coupling partner in the carbene-involved cross-coupling reactions.